CHAPTER THREE
A LIFETIME OF WRESTING A LIVING FROM THE WILDS OF SOUTHERN FLORIDA had made Joe Ashley a hard man. But it also had made him resourceful, practical, and determined, and it had relieved him of any lingering concerns about laws. He was not one to let ethics or propriety stand between him and a dollar. In his book, if you saw a chance to make—or take—a dollar and you stopped to think about right and wrong, you’d probably miss your opportunity. And only a fool would hesitate to take what he could. If the other man wasn’t quick enough or smart enough or strong enough to hold on to it, that was his problem.
Ashley and his family—his wife, five sons, and four daughters—moved from a small settlement near the mouth of the Caloosahatchee River on Florida’s Gulf Coast to the state’s Atlantic coast in 1904. Ashley went to work on one of the crews clearing right-of-way for the Florida East Coast Railway’s relentless southward march to the tip of the peninsula and beyond. Some said that Ashley moved his family because he’d gotten into a gunfight and his seriously wounded opponent had sworn revenge when he recovered.
Aside from matters of style and social graces, Joe Ashley and his clan weren’t too different from many of the other dreamers and fortune seekers who started coming to Florida in a steady stream in the first two decades of the twentieth century. They wanted lots and lots of money. But unlike the persevering preacher’s son who’d opened the door to the state, many of the newcomers felt they were entitled to wealth, and they didn’t have time to work for a lifetime to accumulate it. They wanted it now.
Joe Ashley’s son John had inherited his old man’s worldview, as well as his uncanny skill with firearms. It was said that John could lay a whiskey bottle on its side on a tree stump and, from thirty paces away, put a bullet through the bottleneck so cleanly that only the bottom of the bottle would be broken.
John also inherited his father’s skills as a woodsman. And something—perhaps Joe’s spare-no-rod parenting style—had made John just plain mean.
In late 1911, John, now in his early twenties, went on a hunting and trapping expedition in the Everglades northwest of Fort Lauderdale. During this hunting trip, his youthful greed and impulsiveness and his inherent ruthlessness would prompt him to kill a young husband and father because he wanted something that was worth a small fortune. And he wanted it immediately.
Only the man he killed saw John Ashley commit the crime, but the evidence against him was airtight. He should have swung from the gallows soon after he was arrested and charged with the murder, and the world would have been rid of him. But clever lawyers played the legal system to keep the noose from Ashley’s neck. And his backwoods cunning, his cold-blooded daring, and some plain old good luck took over from there.
For a decade after John Ashley dodged the hangman’s noose, he and his family, aided by a few career criminals who joined them, did pretty much as they pleased in southeastern Florida between Fort Pierce and the Florida Keys. They robbed banks and bootleggers. They made and sold moonshine and hauled whiskey from the Bahamas. They made fools of some cops and killed others, and they eluded capture by intimidating all who would offer evidence against them. And when things got too hot, they disappeared into the Everglades.
John Ashley’s criminal career started with a hunting trip.
In early November 1911, John left his family’s home just south of Stuart for a hunting and trapping expedition in the Everglades. He loaded camping gear, food, a tent, several guns, and dozens of traps into his canoe. He was especially interested in trapping otters. Otter fur was valuable and would fetch a handsome price in Miami and Fort Lauderdale.
But as Christmas approached, Ashley had nothing to show for more than a month in the wilds. On December 19, Ashley stopped at the encampment of Homer Tindall, a young man about his own age who was on a hunting expedition with his father. The Tindalls were camped near the dredge Caloosahatchee, a floating earth-mover that was working on the North New River Canal, a drainage canal being built about twenty-five miles west of Fort Lauderdale.
Ashley stayed in the Tindalls’ camp a couple of days. He and Homer watched Seminole Indians coming and going on the canal, and Ashley wondered if the Indians had had better luck with their traps than he’d had with his.
On the morning of Thursday, December 21, Ashley left the Tindalls’ camp and paddled up the canal to a Seminole encampment a few miles from the Caloosahatchee.
The Seminoles had indeed had better luck, accumulating a pile of eighty-four otter pelts, cured and ready for market. They were worth a lot of money, and John Ashley eyed them enviously.
Among the Seminoles was Desoto Tiger, twenty-five years old and oldest son of Tom Tiger, a Seminole chief who had died about a decade earlier. Like his father, Desoto Tiger was highly respected by his tribesmen. He spoke perfect English and was married with two small children—a boy, four, and an infant daughter.
After eyeing the otter hides, Ashley disappeared for a couple of days.
The crew of the Caloosahatchee shut down to take a Christmas holiday, but on Christmas Day, John Ashley showed up at the dredge with a couple gallons of whiskey. The Seminoles, who were camped nearby, came to the dredge and joined Ashley for an evening of Christmas cheer. Word spread, and soon a sizable crowd had assembled.
It was a relatively tame party for a gang of young men gathered deep in the Everglades with gallons of whiskey. Still, there was a mishap. One of the Seminoles who’d had too much to drink fell from the upper deck of the dredge. Although he was seriously injured, the party continued.
After an evening of boozing, Ashley showed up at the Seminoles’ camp around daybreak. He showed no interest in resuming his hunting and trapping expedition. Instead, he parked himself in the Indians’ camp and started guzzling whiskey. He stayed there several days, drinking. And apparently the way he eyed the Indians’ stack of pelts made them uneasy. The Seminoles tried to get Ashley to leave, but he wouldn’t budge. So they decided to move their valuable stash to the Caloosahatchee, where it would be more secure.
Desoto Tiger was chosen to move the hides to the dredge. Early Friday morning, December 29, 1911, Tiger and Ashley watched other Seminoles load the furs into Tiger’s canoe, which was equipped with a sail. As Tiger got into the canoe to start the trip to the dredge, Ashley asked to join him, saying he wanted to go to the dredge to buy some food. Ashley brought his rifle—a handsome, .38-55 caliber, Model 1894, lever-action Winchester—with him, but left all of his other gear at the Seminoles’ camp. Desoto Tiger placed a pistol in the canoe next to where he would stand to propel the vessel with a pole.
John Ashley and Desoto Tiger left the camp shortly before eight a.m. Around ten a.m., the crew aboard the Caloosahatchee saw John Ashley glide by in a canoe. He was alone.
Later that day, another Seminole took his tribesman who’d been injured Christmas night to Fort Lauderdale to see a doctor.
The following day, Desoto Tiger’s uncle, Jim Gopher, was worried. His nephew hadn’t returned to camp, nor had he been seen since the previous morning when he’d gotten into the canoe with John Ashley. Jim Gopher set out to find his nephew.
He went first to the Caloosahatchee, but the crew there hadn’t seen Desoto Tiger.
Jim Gopher kept looking. He found an oar in the saw grass next to the canal. It was his nephew’s. Clearly something had gone wrong during the short trip from the Seminoles’ camp to the Caloosahatchee.
Jim Gopher went back to the dredge. There, he met his tribesman who’d taken the injured Seminole to Fort Lauderdale. He told Jim Gopher that he’d seen John Ashley in the canal near Fort Lauderdale around four p.m. the previous day. Ashley’s own boat was still in the Seminoles’ camp in the Everglades.
On Sunday morning, December 31, Melville Forrey, the captain of the Caloosahatchee, led a search party seeking Desoto Tiger. Jim Gopher took them to the spot where he’d found the oar. As the wake from their small boat rolled toward the canal bank, a human body suddenly floated to the surface. It was Desoto Tiger. He’d been shot twice.
One bullet had struck him between the eyes and exited the back of his head. The other had struck him in the chest but hadn’t exited. Forrey got out his knife and dug out the bullet. It was a .38-55 caliber slug.
James Girtman couldn’t believe that the sunburned young man who came to his store on Saturday morning, December 30, was John Ashley. The last time he’d seen Ashley, he was a little kid in short breeches. But here he was, and he had otter pelts to sell, eighty-four of them.
Girtman made Ashley an offer—$584 for the lot, and not a nickel more. Ashley thought that was a mighty cheap price. But, he admitted, he hadn’t gone to a lot of trouble to get the hides. He’d trapped some of them and swapped for the others. So he was willing to sell them for what Girtman offered.
Girtman gave Ashley $84 in cash and told him to come back shortly for the rest of the money. When Ashley returned, he was decked out in new clothes. He went with Girtman to a bank, where Girtman cashed a check and gave $500 to Ashley.
It was a lot of walking-around money for 1911—more than $14,000 in twenty-first-century dollars. John Ashley hired a cab to drive him to West Palm Beach. The cabbie dropped him off in what was delicately referred to in those days as the “red-light district.” Flush with cash, Ashley went into a whorehouse, intent on a night of single-minded pleasure.
Ashley’s exuberance got the better of him, however, and soon the cops were hauling him off to jail for recklessly shooting up the house. No one was injured, but Ashley had raised quite a ruckus. The West Palm Beach police hadn’t heard about the killing in the Everglades. Ashley paid his $25 bail, collected his guns—including his prized Winchester—and left town aboard the northbound Florida East Coast Railway passenger train. It was New Year’s Eve, 1911. John Ashley didn’t know it, but he was a wanted man. And it wasn’t because he’d skipped bail for shooting up a whorehouse. He was wanted for murder.
Stories about the brutal murder of a respected Seminole Indian in the Everglades started appearing in newspapers soon after New Year’s Day, and the name “J. H. Ashley” was connected to the crime. Word reached Joe Ashley’s house that the cops were looking for his son. On January 3, 1912, John Ashley said good-bye to his family and headed west for New Orleans. From there, he made his way to San Francisco, and then north to the Pacific Northwest, where he hired on with a logging crew out of Seattle.
The police would learn nothing about John Ashley’s whereabouts from his family. But they didn’t give up the search, nor did the Seminole Tribe.
On January 12, nine days after Ashley’s hasty departure from Florida, a dignified and well-spoken Sioux Indian from Muskogee, Oklahoma, sat down for a special meeting with the Palm Beach County Board of Commissioners. The Native American’s name was James W. Strongheart. He was the grandson of the famous warrior Sitting Bull, and he was related to Desoto Tiger by marriage. He’d come to Florida to try to track down the man who’d killed his in-law.
Strongheart had been to the Everglades, where he’d made his own inquiries into the death of Desoto Tiger. He was convinced that John Ashley had killed Desoto Tiger for the otter pelts.
Strongheart wanted the county commissioners to offer a reward for Ashley, but county attorney H. L. Bussey said the county wasn’t allowed to use public money for that purpose. The commissioners could, however, request Florida governor Park Trammell to offer a reward, and they were willing to do that.
Strongheart was convinced that a large reward would be more likely to get results. So a week after his meeting with the Palm Beach County commissioners, he met with a multimillionaire businessman who’d recently arrived in Miami. The new resident was a Midwesterner, a dynamic, energetic man who had a few ideas for a real estate venture.
Strongheart described the details of the death of Desoto Tiger and explained what he was trying to do. The man who’d killed his in-law was little more than an animal. He had to be captured and brought to justice. A big reward would be a powerful inducement for someone to come forward with information that could lead to his capture and conviction.
The businessman listened to Strongheart’s request and agreed. Tell the newspapers that I’ll kick in a contribution to the reward fund, he said.
Strongheart was elated. He talked to a reporter for the Miami Daily Metropolis at Girtman Bros. Groceries on Twelfth Street, where John Ashley had sold his ill-gotten otter hides a few weeks earlier.
The January 18, 1912, edition of the Metropolis published a front-page, above-the-fold story saying that Carl G. Fisher, “a wealthy resident who is from Indiana,” would pay a $500 reward for information that led to the conviction of the murderer of Desoto Tiger.
The reward for Desoto Tiger’s killer was one of Fisher’s earliest investments in Florida. Before he was finished, he would sink millions more into the community.
Fisher was a grade-school dropout who had made a fortune by inventing the automobile headlight. He was also a founding partner of the Indianapolis 500 in 1911. In 1910 he bought a mansion on a stretch of Brickell Avenue overlooking Biscayne Bay that came to be known as “Millionaires’ Row.”
Fisher bought the mansion sight unseen as a winter vacation home. He would become one of several powerful, wealthy men who became fascinated with Florida around the start of the second decade of the new century. These men—Fisher, William Jennings Bryan, Barron Collier, and others—would build on Henry Flagler’s investment and lay the foundation for Florida’s spectacular growth—and wild real estate speculation—a decade later.
Around the same time that Fisher agreed to offer a reward for the arrest of John Ashley, he met John Collins, who, at the age of seventy-five, had bought property on a swampy, mosquito-infested barrier island about two and a half miles offshore. Collins called his island Ocean Beach, and he was trying to build a wooden bridge across Biscayne Bay to his property. But he’d run out of money.
Collins impressed Fisher, and he loaned Collins $50,000 to complete the bridge. Collins gave Fisher two hundred acres on his island.
Carl Fisher’s wife Jane visited the island with her husband and saw a jungle swarming with mosquitoes. She had no idea why her husband wanted it.
But Fisher, like other dreamers who’d come to Florida before him, saw a paradise.
As Jane Fisher swatted mosquitoes, her husband stood in the middle of the swamp and told her that he was going to build a city here—“a city like magic,” she recalled, “like romantic places you read and dream about but never see.”
Jane Fisher said it was Carl’s “greatest and craziest dream.” He was going to create Miami Beach.
Like Henry Flagler, Carl Fisher realized that his vision for his magic city could only be accomplished if more people came to Florida. But unlike Flagler, whose notion of transportation was the nineteenth-century steam-powered passenger train, Fisher was plugged into the transportation of the future—the automobile. And before automobiles could bring hordes of newcomers to Florida, good roads would have to be built.
So Fisher became a driving force behind two major arteries that would open Florida to the automobile—the Dixie Highway, which ran from the Midwest to Miami, and the Lincoln Highway, which ran from San Francisco to New York City.
The bridge to John Collins’s swampy island opened in June 1913—one month after Henry Flagler died after falling down a flight of stairs in his Palm Beach mansion. The bridge was billed as the longest wooden bridge in the world.
Fisher bought more land, hired a construction crew to clear away man-groves and build bulkheads, and started pumping sand from Biscayne Bay onto his property. In a few years he’d raised most of Ocean Beach to at least five feet above sea level. He planted grass and trees, built tennis courts and golf courses, and planned to turn the island into a sun-and-fun destination that catered to the wealthy. He was so determined that Ocean Beach be associated only with carefree fun that he forbade cemeteries on the island.
But in November 1913, just as Fisher was putting the finishing touches on Ocean Beach, his hopes of attracting tourists were dealt a serious blow when Dade County voters narrowly approved a referendum banning the sale of alcoholic beverages. The polls had scarcely closed, however, before bootleggers were doing a flourishing business.
If Fisher was upset by the vote, the referendum undoubtedly pleased his Brickell Avenue neighbor, William Jennings Bryan, a longtime and passionate advocate of Prohibition. At the same time the bridge to Fisher’s dream-city-to-be was being completed, workmen were putting the finishing touches on Bryan’s new waterfront home overlooking Biscayne Bay. Bryan had decided to build a winter home in Florida for a now-familiar reason: He hoped the climate would improve his wife’s fragile health.
Bryan first visited Miami on Christmas Day, 1909, when he delivered a speech that came to be known as “The Prince of Peace” lecture, in which he affirmed his faith in religion and disputed Charles Darwin’s theory of evolution.
Bryan visited Fort Myers and Miami in January 1912, and hinted that he and his wife were thinking about building a winter home in Miami. He took a quick look at the Everglades and made a boat trip across Lake Okeechobee. The farmer’s son was impressed by the lake area’s rich, dark soil.
“One could hardly believe that there was such an enormous wealth of soil undeveloped, and the area of it amazes me,” he told Miami Daily Metropolis. “I regard the reclamation of the Everglades as one of the greatest enterprises of its kind on record.”
He brought his wife to the village of Miami and Mary Bryan was charmed from the moment she stepped off the Florida East Coast Railway train in May 1912.
“As soon as I breathed the balmy air of Miami I knew this was the place, and began to investigate,” she later recalled.
The Bryans started work on their home on Brickell Avenue soon after he became secretary of state under President Woodrow Wilson in 1913. Bryan rolled up his sleeves and helped the stonemasons build a garden wall on the property.
The Miami Daily Metropolis of April 11, 1913, described Bryan’s new home overlooking Biscayne Bay as a “magnificent and stately structure” that had been designed by Mary to resemble “an old Spanish castle.”
Miami wasn’t the only part of Florida that was getting the attention of wealthy, powerful men. In 1911, Barron Gift Collier, a high school dropout who’d become a millionaire by the age of twenty-six, visited Useppa Island, near Fort Myers on Florida’s Gulf Coast. He liked it so much he bought it, and then he started buying more property, eventually creating his own empire on Florida’s southwest coast.
By 1911, Miami had about six thousand residents, and apparently that was big enough for the federal government to decide to put a US Weather Bureau station there.
At the time, the Weather Bureau was a branch of the Department of Agriculture. The science of meteorology was in its infancy, and a college degree in the field was not required in order to be in charge of a Weather Bureau station. Station chiefs made observations on such things as wind speed and direction, temperatures and barometric pressure readings, forwarding the information on to Washington, DC.
All weather forecasts for all parts of the country came from Washington.
In early May 1911, Richard W. Gray arrived in Miami to be the first “official in charge” of the Weather Bureau station there. His qualifications for the post were meager—a high school diploma from Charlotte, North Carolina, and “various special courses” that included two years’ study of mathematics and languages, according to Department of Agriculture inspection reports written a few years after Gray took the post.
Despite his sparse training in meteorology, Gray’s abilities and efficiency were considered “excellent,” inspector H. C. Frankenfield wrote. But under “special qualifications” for the post, the inspector noted “None.”
Gray, thirty-six years old when he took the job, was “a tall, slender young man of pleasing personality and address,” Frankenfield noted. “His habits are good and his standing in the community is excellent. So far as is known he lives within his means, and he has no source of income other than his official salary.
“Mr. Gray appears to have read and studied extensively, and has passed all of the Weather Bureau examinations with high percentages,” Frankenfield wrote. “He is ambitious and energetic, and can do work of a better class than is required here. He likewise has confidence in his own abilities, and would be glad to change stations, if advanced in grade.”
Gray was “a good man,” Frankenfield concluded, although, at times, he could be “a trifle too loquacious.”
A month after Richard Gray had set up shop at Miami’s new US Weather Bureau station, Solomon Merrick, the minister who had left behind New England’s bitter winters for a sunny citrus farm in Florida, died after an extended illness. His son George, who’d been studying law at New York University, dropped out of school and came home to take over the family’s citrus plantation.
George was an artistic young man who wrote poetry and had won a prize for one of his short stories. It occurred to him that maybe there was a better use for the farm than growing grapefruit. He started thinking about building a city—a beautiful, perfect city.
By late 1913, John Ashley had been away from Florida for two years. He’d spent some of that time working as a logger in the Pacific Northwest. He also claimed later that he’d crossed into Canada and robbed a bank.
He was getting homesick. Although there was the problem of the price on his head and the cops looking for him, he didn’t care. He made his way back home to the family house at the edge of the Everglades.
Still, being a wanted man made him edgy.
On January 27, 1914, Floyd Chaffin, a civil engineer, was riding his motorcycle on a stretch of the Dixie Highway between Stuart and West Palm Beach. Near the little community of Fruita, John Ashley and his younger brother Bob suddenly stepped out of the thick vegetation that lined the highway, pointed guns at Chaffin, and ordered him to stop.
John Ashley aimed a shotgun at Chaffin, identified himself, and accused Chaffin of being a deputy sheriff sent to arrest him. He said he was going to kill all of the deputies in Palm Beach County. I’m a bad man, and I’m wanted all over the country, Ashley told Chaffin. Killing one more man won’t make any difference to me.
Chaffin protested, telling the brothers that he was not a lawman. But it didn’t matter to them. John Ashley hit the engineer with the butt of his shotgun several times, and then Bob pistol-whipped him. But instead of killing Chaffin, they left him lying in the road, injured but alive.
After the attack on the engineer, every cop and sheriff in the area knew John Ashley was back. On February 21, Palm Beach County Sheriff George Baker sent two deputies, S. A. Barfield and Rob Hanlon, to arrest him. The deputies were walking along the Dixie Highway, looking for a break in the jungle-like undergrowth, when John Ashley and brother Bob appeared before them, guns drawn.
The brothers disarmed the deputies and told them to go back to West Palm Beach. But Ashley couldn’t resist taunting the lawmen. Tell Sheriff Baker not to send any more “chicken-hearted men” after him, he said.
It was hard for the Ashley clan to understand why the law was going to so much trouble to arrest John. The dead man was a Seminole Indian. What was all the fuss about?
Finally, the family made a cynical calculation. John would turn himself in and stand trial for the murder of Desoto Tiger. The way the Ashleys figured, there weren’t twelve men—women couldn’t serve on juries at the time—in Palm Beach County who would convict an Ashley for shooting a Seminole. No one who was a friend of the family would vote for a conviction. And anyone who wasn’t a friend knew they’d face the furious wrath of the clan if they voted to convict John Ashley of a crime that could send him to the gallows.
Ashley made arrangements through an attorney to surrender to Palm Beach County sheriff’s deputies. He promised to behave himself under two conditions: He didn’t have to submit to being handcuffed when he was moved from the jail to the courtroom during the trial, and his father could bring his supper every night to the Palm Beach County Jail. Sheriff Baker agreed, and Ashley turned himself in on April 27, 1914.
Ashley’s trial began in West Palm Beach a couple of months later. The Ashleys’ gamble was shrewd, but not quite shrewd enough. On July 1, the jury retired to deliberate. When they returned, they told the judge they were deadlocked. Nine of their twelve members had voted, as the Ashleys figured they would, for acquittal. But three had dared to vote to convict John Ashley of murder.
It wasn’t quite enough to get John Ashley off the hook. He’d have to stand trial again. Still, he continued to behave as a model prisoner. And undoubtedly he still believed, with good reason, that there weren’t twelve men in Palm Beach County who’d be crazy enough to convict him.
In the closing days of John Ashley’s trial in West Palm Beach, while the jury of twelve listened to attorneys sparring over how a man was killed in the wilds of the Everglades more than two years earlier, another man was killed in Europe.
On June 28, 1914, an angry young man with a gun killed a member of the ruling family of Austria-Hungary and his wife, who were visiting Sarajevo, Austria. The young gunman’s name was Gavrilo Princip. Like countless assassins throughout history, Princip, a Serbian, believed that by killing Archduke Franz Ferdinand, heir to the throne of Austria-Hungary, he was striking a blow against a monstrous evil. What he’d actually done, however, was tip the first domino in a sequence of events that would ignite four years of slaughter in Europe.
The carnage that followed the deaths of two people in Sarajevo would change the world almost beyond recognition.
Before the war ended in 1918, more than sixty-five million servicemen from the United States, Britain, Germany, France, and many other countries around the world would be engaged in the conflict. More than eight million of them would die, along with nearly seven million civilians.
Although the murder of Franz Ferdinand and his wife was a brutal act, it did not have to ignite the greatest conflagration that the world had ever seen. The war happened because the assassination activated an entanglement of alliances and treaty obligations that quickly divided Europe into two opposing armed camps. In a sense, the conflict that came to be called the Great War happened because honor demanded it. And the weapons the belligerents wielded were frighteningly efficient, modern killing machines—rapid-fire machine guns, powerful artillery, airplanes, battleships, and submarines. It was the first time such deadly weapons had been deployed on so large a scale.
“All this madness, all this rage, all this flaming death of our civilization and our hopes has been brought about because a set of official gentlemen, living luxurious lives, mostly stupid, and all without imagination or heart, have chosen that it should occur rather than that any one of them should suffer some infinitesimal rebuff to his country’s pride,” British philosopher Bertrand Russell wrote in August 1914.
The story of the faraway assassination received prominent play on the front page of the Miami Daily Metropolis of June 29, 1914, although the killer was referred to as a “Servian” student. In fact, the newspaper’s editors misspelled “Serb” and “Serbian” throughout the story as “Serv” and “Servian.”
On the day that Franz Ferdinand and his wife Sophie were gunned down, the world still moved at a relaxed, nineteenth-century pace. Four-legged horsepower still was a primary means of transportation. Steam powered the locomotives that pulled trains and powered ships at sea, but there were plenty of sleek schooners that used the ancient propulsion of the wind.
Still, the technology that would change the world in a few years had appeared. Airplanes, primitive though they were, had been around for a decade, and would play a role in the war that was about to erupt in Europe. Automobiles powered by gasoline-fueled internal combustion engines were becoming common, although for long trips Americans still used the steam-powered passenger train.
The United States had ratified the Seventeenth Amendment to the Constitution in 1913, allowing voters in each state to choose the two senators who would represent them in the US Senate. Before the amendment, US senators had been chosen by individual state legislatures.
But the voters who went to the polls to choose those senators were males only, just like the jury in West Palm Beach that had been unable to come to a decision about whether John Ashley was guilty of murder. Women could not vote, nor could they serve on juries.
The outbreak of war in Europe in 1914 proved to be the undoing of William Jennings Bryan as secretary of state. Bryan was a firm believer that civilization was steadily moving humanity to a utopian destiny, when hunger, poverty, and wars would be eliminated. He was horrified as Europe stumbled inexorably toward a massive armed conflict. As Germany and the Central Powers squared off against the Allies—primarily Great Britain and France—Bryan insisted on a policy of strict neutrality toward the belligerent nations.
That was in line with President Woodrow Wilson’s stated policy—at least, technically. But while Bryan had volunteered for military service during the Spanish-American War, he abhorred war and wanted to stop the fighting in any way possible, even if it left Britain and France at a disadvantage. And his concept of neutrality was so strict and narrow that he even refused to publicly condemn Germany when a German submarine torpedoed the British passenger liner Lusitania in May 1915. The sinking killed 1,198 civilians, including 128 Americans.
Germany claimed that the ship had been carrying war munitions for the Allies and therefore was a legitimate target of war. Bryan didn’t dispute the German assertion.
Relations between Bryan and President Wilson became tense. Bryan submitted his resignation on June 8, 1915. He was a private citizen again, free to pursue other interests.
After the mistrial a few months earlier, John Ashley had spent the summer and much of the fall of 1914 behind bars in West Palm Beach, awaiting a new trial. No judge in his right mind was going to allow bail for a prisoner who had eluded cops for two years before turning himself in. Ashley kept his bargain about behaving, however, so he was never handcuffed, and he was allowed to receive home-cooked suppers from his mother while he was in jail.
Ashley’s second trial started on November 11, 1914. The courtroom was packed with spectators and men called to serve as potential jurors. Judge Pierre Branning called the courtroom to order, then told the 150 potential jurors that any of them who were sick or deaf or had urgent business would be excused from duty.
“In an instant there was a rush to the front of the courtroom and about every ailment known to doctors was given out,” reported the Stuart Times. “In fact, Judge Branning was surprised to hear of so much sickness.”
About seventy-five jurors—half the pool—were excused. When all of those who remained had been questioned by prosecution and defense attorneys, only two had been chosen. It was abundantly clear that there were not a dozen men in Palm Beach County who were willing to sit in judgment of an Ashley.
The Ashleys didn’t need an attorney to tell them that if a jury couldn’t be selected in Palm Beach County, the judge would grant the prosecution’s relentless requests to move the trial to another county. And a trial in another county in front of a jury they couldn’t control either through friendship or intimidation could mean an unhappy outcome for John Ashley.
The Ashleys didn’t like the odds. So on Saturday, November 15, Joe Ashley and his clan executed what could be called the “pork chop plan” to free John Ashley from jail.
Court was in session that day, but once again, no jurors were chosen. After the session ended but before John Ashley left the courthouse, Joe Ashley asked his son what he wanted for supper.
“John, do you want some good beefsteak for supper?” Joe Ashley asked.
“Yes,” John answered.
“Wouldn’t you rather have pork chops?” Joe suggested in a way that Sheriff Baker thought was a bit odd.
“Sure,” John answered.
John Ashley then left with Robert Baker, a deputy sheriff who was the jailer, and also the son of Sheriff George Baker.
As usual, Ashley was not in handcuffs when he got into an automobile with Baker for the short ride from the courthouse to the jail. It was a dark and rainy night as Baker drove through the streets of West Palm Beach with his prisoner. Still, it wasn’t dark enough to prevent Baker from recognizing Joe Ashley and one of his sons standing across the street from the jail.
As Ashley and Baker were walking from the car into the jail compound, Baker’s wife called to him from the cottage next to the jail that she shared with her husband. She handed Baker a plate of pork chops that Joe Ashley had left for his son.
Baker and John Ashley walked to the entrance of the jail, and Baker handed his prisoner the plate so he could have both hands free to unlock the gate. He turned and put the key into the lock.
The next thing he heard was the sound of breaking glass, and when he turned around, he saw John Ashley disappearing around the corner. Still, there was a ten-foot fence surrounding the compound. No one could scale that without help.
Baker drew his gun and raced after his prisoner. In the darkness he heard Ashley blindly run into the fence. He fired a shot in the direction of the sound, and then ran to the fence.
Ashley was gone. The fence was intact. It was as though Ashley had simply melted through the wire. Baker took off in the direction that he thought Ashley would have gone, but there was no trace of him.
Sheriff George Baker told the Daily Tropical Sun of West Palm Beach that he thought the conversation between father and son about supper was a prear-ranged signal. His father’s suggestion that John have pork chops for supper was a signal that it was time for him to break out of jail.
“It is supposed that a skiff or canoe with weapons and provisions had been furnished by his friends and put in some place known only to them and him so that he knew where to go and by this time is a long ways out in the Glades,” the Tropical Sun concluded.
John Ashley stayed out of sight for a couple of months after his escape. But in February 1915, with winter tourists and money coming into Florida, the clan came out of hiding.
In 1894, the Florida East Coast Railway built a railroad drawbridge across the St. Lucie River, just north of Stuart. Eventually, seagulls learned that when a passenger train crossed the bridge, there was a good chance that food scraps would be thrown out of the dining car.
Soon Stuart residents could tell when a passenger train was approaching because gulls would alight on the bridge to await the train. They would be on the bridge long before the train’s whistle was heard. Residents noted that they never assembled on the bridge in advance of freight trains.
Shortly after sundown on Sunday, February 7, 1915, the gulls settled on the bridge in anticipation of the arrival of a southbound trainload of tourists on the Palm Beach Limited. It was the peak of the winter season, and the luxurious Florida East Coast (FEC) Railway train, nicknamed “The Millionaires’ Special,” was hauling a load of well-heeled northern visitors—many of them New Yorkers—to Palm Beach. The train included an observation car with an open-air platform, where passengers could watch the tropical vista slide by.
Steam-powered locomotives were required to make regular stops to take on water for their boilers, and the Palm Beach Limited stopped at a water tank in Stuart. As the train started pulling away from the tank, but before it could pick up speed, four agile young men wearing masks dashed out of hiding and climbed onto the observation platform. They pulled out pistols and told the passengers to raise their hands.
Some of the women screamed at the sight of the guns, but one of the would-be robbers shouted that they did not want anything from the women. One of the men herded the women into another passenger car.
The bandits started to demand valuables from the men, but someone pulled the emergency stop cord, and the train screeched to a sudden halt. The bandits leapt off the train and ran.
For all of their gun-waving, they hadn’t made much of an impression on the Yankee tourists.
“They were young fellows, and they looked like farmers,” Margaret Wilson, a passenger from New York City, told the New York Times. “They seemed frightened.”
Still, an armed holdup of a passenger train full of wealthy tourists made national headlines. “Bandits Lose Nerve and Run from Prey,” read a front-page headline in the Washington Herald edition of Monday, February 8, 1915.
A sheriff’s posse mounted a vigorous effort to capture the would-be train robbers, and soon had four suspects in custody in Stuart. But the men turned out to be drifters who’d been in the wrong place at the wrong time, and they were released.
With the release of the tramps, however, suspicion automatically turned to the Ashleys, and Sheriff Baker and his posse were determined to find them. They continued beating the bushes through the night and into the next morning. This set the stage for an ironic comedy of errors that could have had a tragic ending, but luckily led only to embarrassment.
It so happened that silent film director George Terwilliger was filming a shoot-’em-up thriller in Florida for Lubin Studios of Philadelphia. The film starred two heartthrobs of the early days of motion pictures, Ormi Hawley and Earl Metcalfe.
The script included a scene in which armed robbers boarded a train and robbed the passengers, and Terwilliger had made arrangements to shoot it on the FEC’s tracks, just across the St. Lucie River from Stuart.
On Monday morning, the southbound train carrying Terwilliger and his film crew and actors stopped at the raised drawbridge that spanned the river. Terwilliger started putting his actors through a very realistic rehearsal. Men with guns climbed aboard the train and pointed them at passengers, who appeared to be horrified.
The sheriff’s posse, still hunting for the previous night’s robbers, saw what was happening.
“Then,” reported the Philadelphia Evening Ledger, “things started.”
“Several shots were fired, whether as a signal to other sheriffs or at the Lubin players has not been cleared up as yet,” the Ledger said, “but from every direction armed man-hunters carrying rifles appeared.”
The actors, now genuinely terrified, scattered as men brandishing weapons swarmed aboard the train.
“Some fled into the train—others stood still, frightened still, thinking they were about to be held up by a band of Florida robbers,” the Ledger reported. “Three of the sheriffs grabbed two of the Lubin ‘robbers.’ Everyone talked, no one understood.”
Amid the chaos and shouting, director Terwilliger noticed that one of the men waving a gun was wearing a lawman’s badge. Terwilliger grabbed the man by his suspenders and shouted “Moving pictures! Moving pictures!”
“Light then began to dawn on both sides,” the Ledger said. “The sheriff explained to Terwilliger and the latter explained to the sheriff.”
Guns were lowered and holstered, pounding heartbeats subsided; there may even have been a few laughs. And the posse apparently was stagestruck.
“After the company had recovered from fright, rehearsals were resumed,” the Ledger reported, “and the sheriff and his deputies, at their own request, acted in the pictures and then resumed their manhunt.”
A guide leading a group of hunters in the Everglades may have accidentally found what lawmen had been seeking—one of the Ashleys’ hideouts. Around nightfall on February 16, C. C. Myers and a boatload of tourist hunters were about to land on a canal bank to set up camp for the night. Suddenly a man with a shotgun appeared on the opposite bank of the canal.
“If you want to see blood, make your campfire there!” the man shouted. Then he raised the shotgun and fired.
Myers was hit in the back by the pellets. The hunters fled. Myers survived the painful attack.
They couldn’t identify the angry gunman who’d shot Myers, but the cops assumed it was an Ashley. And lawmen also thought the Ashleys had robbed a store in Deerfield, a small village south of West Palm Beach, a few days later.
On Tuesday, February 23, the Ashleys committed the crime that would clearly demonstrate to local lawmen that they were dangerous criminals. On that morning, teller A. R. Wallace was absorbed in taking a deposit from a customer at the Bank of Stuart. A movement caught his eye and he glanced up.
He was looking up the muzzle of a rifle that was pointed at him by Bob Ashley, kid brother of John Ashley.
“Hands up!” Bob said.
Wallace thought he was joking.
“Hands up!” Bob Ashley repeated more forcefully.
Wallace glanced around and saw that John Taylor, the bank’s cashier, had his hands in the air.
“Better put ’em up, Wallace,” Taylor said. “He means it.”
Wallace raised his hands “All right,” he said. “What’s next?”
John Ashley, a gun in each hand, waved one of his pistols at Wallace. He tossed a sack at the teller. “Throw it in here, that’s what’s next,” he said.
There was about $4,300 in bills and coins within sight of the robbers, and Wallace started tossing it into the sack. But he did not open any drawers containing more cash, and Ashley apparently was unaware that there was more cash at hand.
Wallace picked up a sack containing about $30 in pennies.
“Throw it in,” Ashley commanded.
Another gun-toting robber appeared. His name was “Kid” Lowe, a hardened criminal from Chicago who’d come south and somehow connected with John Ashley.
Lowe asked how much money was in the sack.
Told there was about $4,300, Lowe was angered.
“Where’s the rest?” he demanded, shoving a gun in Wallace’s face.
“There is no more,” Wallace said. “This is a small bank and has only a small supply of cash.”
Lowe grabbed Wallace and shoved him into the lobby, where several other terrified customers were waiting.
“Which one of you fellows can run a car?” Lowe demanded.
A customer named Frank Coventry said he could drive a car, and Lowe ordered him to drive the three robbers out of town.
What happened next has been debated for nearly a century.
Somehow, John Ashley was shot in the head but miraculously not killed. One account of the incident says Bob Ashley fired his gun in jubilation at the successful holdup and accidentally hit his brother. Another account says that as Coventry was driving out of town, Kid Lowe turned to fire a shot to discourage anyone who might be pursuing them, and the bullet struck one of the car’s window frames, ricocheted, and struck Ashley. Still another explanation was that Ashley accidentally shot himself with his own gun. And Ashley later would claim that Lowe was trying to kill him so he wouldn’t have to give Ashley a share of the loot.
However the shot was fired, the bullet struck Ashley below the chin and lodged behind his right eye. Somehow, he was not killed, but it was a severe wound—one that probably would have been fatal if left unattended.
Coventry sped south on the Dixie Highway. Ashley was losing a lot of blood from his wound and passed out briefly, Coventry said later. About ten miles south of Stuart, Coventry was ordered to stop. The three robbers got out. Coventry was told to return to Stuart, and if he so much as looked back as he was driving away, they’d kill him.
Coventry later told police that the three had horses waiting for them when they got out of his car. Despite his wound and weakness from loss of blood, John Ashley was still able to mount a horse and gallop into the swamp, Coventry said.
As they disappeared into the Everglades, carloads of heavily armed men were speeding after them. They knew the fugitives would head for their familiar hideouts. At one point that afternoon, the lawmen were certain they had their quarry surrounded. But John Ashley’s intimate knowledge of the Everglades saved them, and somehow they eluded the posse.
By nightfall, about a hundred men, some of them on horseback, were thrashing through the Glades, looking for the bank robbers. John Ashley, still losing blood, was weakening and in intense pain. Still, he managed to elude the posse for two days.
Finally, he’d had enough. Ashley gave himself up on the morning of February 25.
But Bob Ashley and Kid Lowe were still on the run, and they’d taken the money with them.
The cops took John Ashley straight to a surgeon’s office in West Palm Beach. By that night, he was back in the Palm Beach County Jail. Eventually, he would wear a glass eye in the socket where his right eye had been.
While the cops-and-robbers drama was playing out in the wilds of southern Florida, Edwin Menninger, a student at Washburn College in Topeka, Kansas, was busy preparing for a career in medicine. He hadn’t given too much thought to his choice of professions. His father was Dr. Charles F. Menninger, a renowned psychiatrist. His brothers Karl and Will were also planning careers in medicine. It was a family tradition.
In 1915, Edwin Menninger was a senior at Washburn. He’d studied chemistry for three years, and now was applying himself to organic chemistry.
But he had other interests, including journalism. As a boy, he’d shown unusual skill in managing his newspaper-delivery routes. They were well-organized, and he had developed an effective system for collecting from his subscribers and adding new ones.
He was associate editor of the student-produced newspaper, the Washburn Review. And he enjoyed the art of legerdemain.
He also enjoyed experimenting with chemicals. This, however, was a pleasure that would change the course of his life.
On March 2, 1915, Menninger and a fellow student were experimenting with chemicals in a laboratory in Rich Hall on the Washburn campus. They mixed phosphorus and potassium chlorate in a test tube. Menninger knew that he’d created a volatile, highly unstable combination. They decided to take the mixture outside to test it.
Menninger carried the glass test tube in his right hand. Without thinking, he shifted the tube to his left hand, upending it in the process.
That slight movement of the chemicals was all that was needed to agitate and ignite the compound. There was a blinding flash and the test tube was shattered in a shower of sparks and broken glass. Like John Ashley, Menninger lost his right eye, and his left hand was severely mangled. His plans to become a medical doctor were destroyed as well. When he recovered, he would leave Kansas for New York City to enroll in the Columbia University School of Journalism.
While Dr. Charles Menninger tried doggedly to save what remained of his son’s left hand, a grand jury in West Palm Beach heard evidence against John Ashley for robbing the Bank of Stuart the previous month. On March 10, Ashley was indicted, along with Kid Lowe and Bob Ashley, on charges of bank robbery. Lowe and the younger Ashley were still on the run, however.
John Ashley still had to answer for the death of Desoto Tiger.
On March 22, Ashley was in court in West Palm Beach for the third time to face the charge of murdering the Seminole Indian. Prosecuting attorneys had made a vigorous effort to get the trial moved to another county, arguing that a jury in Palm Beach County would be afraid to bring in a guilty verdict. But Judge Pierre Branning had sided with Ashley’s defense attorneys in refusing a change of venue.
The judge soon changed his mind, however. Attorneys questioned 112 potential jurors, trying to seat a dozen to hear the evidence. Only two were chosen. All of the others told Branning that they’d already made up their minds about whether John Ashley was guilty or innocent and thus could not be impartial.
Branning gave up. The trial would be moved to Dade County.
John Ashley was in jail when the judge made his decision. It was a serious blow to his hopes for being acquitted of the murder charge. Nevertheless, he put up an optimistic front.
“All I want is a fair and impartial trial, and I believe I can get it in Miami as well as I could here,” he told a reporter for the Daily Tropical Sun.
Whether John Ashley actually believed what he said is another question.
In 1909, L. D. Reagin, publisher of the Sarasota Times, set out on an automobile trip from Tampa to Jacksonville. At the time, those cities were two of Florida’s leading seaports.
There’s no record of what kind of car Reagin was driving, but at the time a Ford Model T was capable of forty to forty-five miles per hour on a good road. And the roads between Tampa and Jacksonville were not the best.
It was a trip of around three hundred miles. Had Reagin been traveling in a Model T on roads that would have allowed him to push the car to its top speed for the entire distance, he could have made the trip in roughly six and a half to seven and a half hours.
Reagin made the journey in nineteen hours, for an average speed of about sixteen miles per hour. Still, in 1909, it was the fastest anyone had ever made the trip between Tampa and Jacksonville in an automobile.
By 1915, it was becoming abundantly clear to Florida’s business leaders that there had to be a better way to link the state’s Gulf and Atlantic coasts. And businessmen on the Florida Gulf Coast especially wanted an overland route from southwest Florida to Miami, which even then was on its way to becoming an important seaport on the state’s east coast.
But between Tampa and Miami lay hundreds of miles of dense jungle and saw-grass prairies. Most engineers took one look at terrain that was as mysterious as the surface of the moon and concluded that a road simply could not be built through that impenetrable swamp.
Still, a few dreamers were willing to try. In April 1915, Francis W. Perry, president of the Fort Myers Chamber of Commerce, and James F. Jaudon, the tax assessor for Dade County, sat down in Tallahassee to talk about a road connecting Tampa and Miami. They got a map of the state from Florida commissioner of agriculture William McRae and studied it closely.
Lake Okeechobee, the giant, shallow lake that serves as a holding pond for water before it flows slowly southward through the Everglades, was the northern boundary of the Glades. From the southern shore of the lake to the tip of the peninsula was almost entirely covered by jungle, saw-grass prairie, and a shallow sheet of water sliding through the Glades to Florida Bay.
You could travel by automobile on roads of varying quality from Tampa southward to Fort Myers, a distance of around 145 miles. But the only way to get from Fort Myers to Miami was to either go by boat southward around the tip of the peninsula or embark on an automobile trip of perhaps 750 miles that would have required going north to somewhere around Gainesville, then turning east to St. Augustine, and finally, a trip of more than 300 miles south down the east coast to Miami.
As Jaudon and Perry studied the map, they knew that carving a road through the Everglades would be a fiendishly difficult task. But even their unbridled imaginations couldn’t conceive just how difficult it would be.
“The unknown character of the immense terra incognita through which the highway was projected could not be determined by engineers trudging through miles of aquatic prairie,” an anonymous author wrote in a booklet about the construction project in 1928. “Not until actual construction was attempted did the discouraging features of the undertaking become adequately known.”
Had Jaudon, Perry, and others who took up the cry to pierce the Everglades known what they actually were up against, they might not have taken on the project. No one would have blamed them for throwing up their hands and declaring that it couldn’t be done.
Still, it was an age when anything seemed possible. The Panama Canal had been built to link the Atlantic and Pacific Oceans, and Henry Flagler had laid down a railroad across the Florida Keys to Key West. Why couldn’t a road be built through the Everglades?
Jaudon and Perry started talking to other movers and shakers in Florida. The idea started gaining momentum.
Judge Pierre Branning issued some special instructions to guide the selection of the dozen Dade County men who would sit in judgment of John Ashley in his third trial for the murder of Desoto Tiger: They must have no prejudice against Indians, they must be willing to consider an Indian’s testimony the same as they would a white man’s, they must have no prejudice against hearing testimony through an interpreter translating the Seminole language, no reluctance to impose the death sentence should evidence convince them beyond a reasonable doubt that the defendant was guilty, and no predetermined opinion about John Ashley’s guilt or innocence.
It took a couple of days to get through the selection process, but on April 2, 1915, a jury in Miami started hearing the evidence. Newspaper reporters covering the first day of testimony wrote that the accused was in good spirits.
But his mood changed as the trial progressed.
The jury heard the story of Desoto Tiger’s death—valuable otter pelts belonging to the Seminoles, Tiger found dead from two gunshot wounds, pelts sold by Ashley in Miami.
Ashley still wore bandages around his head from the gunshot wound he’d suffered after the robbery of the Bank of Stuart two months earlier. Bandages completely covered where his right eye had been.
“For the most part he sits grim and silent,” the Miami Daily Metropolis reported, “thin lips pressed tightly together—always watching the witness.”
His mother, Lugenia, equally grim, sat beside him with his lawyers at the defendant’s table. “Never a change comes across her countenance, except when she turns to speak a word to her son in answer to some question,” the Metropolis reported. “Statement after statement comes from the witnesses, never causing her to wince or smile.”
A few days into the trial, the prosecution brought in a surprise witness who sent defense attorneys into paroxysms of protest. His name was Homer Tindall, and he’d talked with John Ashley when Ashley dropped by his campsite a few days before Desoto Tiger was killed.
Tindall had not testified during Ashley’s first trial that had ended in a hung jury in West Palm Beach. After hours of heated arguments that stretched over two days, Judge Branning ruled that Tindall’s testimony could be heard by the Miami jury.
Homer Tindall and his father had been camped about a mile and a half from the Caloosahatchee, the dredge that had been working on the drainage canal. Ashley spent the night of December 19 at the Tindalls’ camp.
Around noon the following day, Ashley and the younger Tindall watched two Seminoles glide past their camp in a canoe in the canal.
“The Indians were coming up to the camp and they were some little distance away, and he, Ashley, asked me if I knew them and I told him I did not,” Tindall testified, “and he asked me if I reckoned they had any hides, and I told him I didn’t know, and he said, ‘If they have let us kill them and get the hides.’ He said, ‘We can do it and no one will ever know it,’ and I told him ‘No,’ and he said, ‘If I could find one with a large quantity of hides I wouldn’t any more mind killing him than I would of shooting a buzzard,’ and at that time the Indians were at the camp and there wasn’t any more said.”
Tindall said Ashley had stayed in their camp until December 21 and then left; he’d had no further contact with him.
The jury also heard James Girtman testify that he had bought eighty-four otter pelts from Ashley for $584.
When Ashley took the stand, he said he and Desoto Tiger had discussed the hides privately in Ashley’s tent, and that Ashley had wanted to buy the pelts but first wanted to get an opinion about what they were worth. Ashley said he told Tiger that he’d go to Fort Lauderdale to get an estimate, and that Tiger had insisted that he bring back whiskey.
Ashley said when he returned, he paid Tiger $400 for the hides on December 28, and this transaction also was in the privacy of his tent. He denied saying to Tindall that he would as soon shoot a buzzard as an Indian, and accused Tindall of accepting a bribe in exchange for his testimony.
Ashley told the jury that he’d shot Desoto Tiger in self-defense while they were in Tiger’s boat. The Seminole had pointed a pistol at him and threatened to kill him unless he gave him whiskey.
“He had his pistol pointing at me, and I, hearing the click of the pistol, grabbed my gun and started shooting as fast as I could,” Ashley told the jury.
Desoto Tiger tumbled out of the canoe and into the canal, Ashley said.
But the jury didn’t buy John Ashley’s story. On April 8, 1915, they pronounced Ashley guilty of murder. The following day, Judge Branning sentenced Ashley to hang. When he heard the sentence, Ashley looked toward the attorney who had led the prosecution’s case against him. A cool, chilling smile slowly came to his lips.
Ashley’s court-appointed defense attorney, Crate D. Bowen, said he would appeal the conviction. In the meantime, Ashley would be held in the Dade County Jail in Miami awaiting trial on charges of robbing the Bank of Stuart a few months earlier.
Some people who were acquainted with Joe Ashley attributed his contempt for the rule of law to the fact that he grew up in the post–Civil War South during Reconstruction, when US troops occupied the former Confederate States for more than a decade. Whatever the reason, he certainly did not respect traditional boundaries of behavior and property ownership.
He saw no harm in robbing banks. In fact, he considered it a public service. The money they took was insured and would be replaced by “some damned Yankee insurance company.” So the bank did not lose anything, the depositors didn’t lose anything, and since the Ashleys would spend the money locally, it was actually a form of economic stimulus. So instead of forming posses to chase them down, “Everybody ought to help us,” was the way Joe Ashley saw it.
So it stood to reason that Joe Ashley and his family were not going to allow the state of Florida to hang his son for the murder of a Seminole.
Dade County Sheriff Dan Hardie knew he had a slippery prisoner on his hands, and that John Ashley’s family was likely to try to free him. He added locks and chains to increase security.
The Ashleys’ jailbreak attempt came in a sudden, brutal, and deadly fashion on June 2, 1915.
Workers at a multistory parking garage across the street from the Dade County Jail talked to three men—one older, the other two younger—who were hanging around the garage that morning as though they were waiting for something to happen.
The men wanted to make sure a Ford automobile parked in the garage would start with no problems. They bought new batteries for the car and installed them.
“I tried to talk to them but none of them seemed very talkative and our conversation was not long,” E. T. Wells, who worked at the garage, told the Daily Tropical Sun later. “The men all seemed to be nervous, and I remember now that one or the other frequently went to the doors or windows and looked out.”
One of the younger men was Bob Ashley, John Ashley’s kid brother. Ashley had bought a bottle of whiskey earlier that day, and he was carrying a curious package, something long and slender and wrapped in blue paper. A garage employee later said Ashley occasionally went to a window or door of the garage to communicate in sign language with someone in the jail across the street.
Around 12:30 p.m. Bob Ashley made a daring move. He crossed the street from the parking garage to the jail and knocked on the door of the adjoining house, where Deputy Sheriff Robert Hendrickson, the jailer, lived with his wife. When Hendrickson came to the door, Bob Ashley shot him dead with a rifle that had been wrapped in the blue paper. He grabbed the keys to the jail, and ran.
Hendrickson’s wife grabbed a shotgun and aimed at the fleeing Bob Ashley, but the gun either misfired or wasn’t loaded.
In the parking garage across the street, Joe Ashley and Kid Lowe were talking to employees on the second deck of the building when they heard a gunshot. Ashley and Lowe ran to a window. They watched for a few moments, then started down the stairwell, one of them remarking that Miami didn’t seem to be a very safe town, and that they’d better leave and go home.
Across the street, the gunshot that had killed the jailer was attracting a crowd, and Bob Ashley apparently lost his nerve. He dropped the keys and fled back into the garage. Not seeing his father or Kid Lowe, he ran to the Ford with the recently installed new batteries.
But Bob Ashley couldn’t operate a car. He pointed his gun at a man standing nearby and ordered him to get in the car and drive it. The man replied that he did not know how to drive a Ford.
Ashley leveled his gun at a second man and demanded that he get in the car to drive. But that man also said he did not know how to drive a Ford.
So Ashley accosted a third man and shouted to him to get in the car. But the man was hard of hearing, and when he cupped his hand around an ear and asked Ashley to repeat what he’d said, the young gunman gave up and ran from the garage and out onto the street.
Ashley waved his gun and stopped a man driving a cycle car, a small, cheap automobile with room for only the driver and a passenger or two. Ashley shoved the gun in the driver’s face and ordered him to drive him out of town. The driver realized the police were after Ashley and refused, but Ashley became enraged and threatened to kill him. Reluctantly, the driver made room for Ashley in his small car and drove away.
But after going a few blocks, the car stalled and the driver got out, raised the hood, and started tinkering with the engine. By this time, Miami police officer Robert Riblett had overtaken Bob Ashley. Riblett pointed his gun at Ashley and ordered him to surrender.
Again, there are varying accounts of what happened next. Some say that Riblett and Ashley grappled hand to hand before the shooting started. Others say Ashley whirled and fired twice at Riblett, and then the police officer managed to get off a shot that hit Ashley in the abdomen.
Both men were mortally wounded. Riblett died shortly afterward at a hospital. Bob Ashley was examined by a doctor, who said there was nothing he could do. He was taken to a jail cell. Sheriff Dan Hardie sat down on his bunk, hoping to get deathbed information from Ashley. Ashley admitted he’d planned to break his brother out of jail, but he refused to tell Hardie anything more about his family, and soon he was dead.
John Ashley, of course, denied knowing anything about a plot to spring him. Jailers then discovered that he’d secretly been using a spoon to tunnel his way out of his cell, and was on the verge of succeeding. He was moved to a more secure cell, presumably to await his date with the hangman’s noose. But the Florida Supreme Court had agreed to hear the appeal of his conviction for the murder of Desoto Tiger, so he had escaped the gallows—at least for the time being.
A few days later, Sheriff Hardie received a crudely written letter, addressed to “Mr. Dan Hardie, high sheriff of Dade County.”
“Dear Sir,” it began, “we were in your city at the time one of our gang young Bob Ashley was brutally shot to death by your officers and now your town can expect to feel the results of it any hour. And if John Ashley is not fairly delt with and given a fair trial and turned loose simply for the life of a god damned Seminole indian, we expect to shoot up the hole god damned town, regardless of the results might be. We expect to make our appearance at an early date, signed, Ashley gang.”
The letter was signed “Kid lowe Arizona kid ike Mitchell and others name not mentione.”
Nothing came of the threat, and Hardie dismissed it as a hoax. Apparently, the Ashleys were willing to wait for the state Supreme Court to decide on the appeal.
While lawmen in Miami and Palm Beach counties tried to contain and curtail the crude but crafty savagery of the Ashley clan, local politicians moved forward with plans to try to tame a natural force that was wilder than the Ashleys—the Everglades.
A week after the gunfight in downtown Miami, in which three men were killed, a group of businessmen met in Orlando to form the Florida Highway Association. Among the discussion items on their agenda was the proposed highway through the Everglades, linking Tampa and Miami. It needed a catchy name. The Tamiami Trail—a clever name that managed to be both alliterative and combine the names of the cities that would be linked—emerged from the discussion.
Preliminary plans called for the Trail to go through only two counties, Dade on the east coast and Lee on the Gulf Coast. Each county would be responsible for paying for the portion passing through it.
In 1915, the boundaries of Lee and Dade met in the middle of the state near the tip of the peninsula. Both were large counties, and in 1915, Lee County—which included Fort Myers—was bigger than the state of Delaware. Dade County’s segment of the Trail would be around thirty-five miles. Lee County’s portion would be more than twice that. Lee did not have the rapidly growing population and tax base that Dade had, and thus had fewer resources to pay for its share of the highway.
On September 8, the Dade County Board of Commissioners—who would have to approve any plan to pay their county’s share of the construction costs—heard from some of the doubters about building the Trail. J. H. Tatum told the commissioners that draining the Everglades to build the road would flood Dade County, and he was unalterably opposed to spending so much money to simply flood the county. He also had doubts about whether Lee County would ever build its share of the highway, and that would mean all the money Miami spent on the road would be wasted because it would be a road to nowhere.
At times the debate over whether to build the road grew heated. Then the meeting was interrupted by a telegram. The Lee County Board of Commissioners had just decided to hold an election on October 19 to determine whether the county would issue bonds to pay for its portion of the Tamiami Trail. Dade County voters would decide the same issue on the same date.
Around the same time that Dade and Lee County leaders were discussing the Tamiami Trail, representatives from the ten states through which the Dixie Highway would pass, from Michigan to Florida, met in Chattanooga, Tennessee, to discuss the road’s route. Regardless of where the highway meandered from its origin in Montreal, however, it would end in Miami, functioning like a pipeline for winter-weary Midwesterners seeking sunshine.
Lee County and Dade County voters approved issuing bonds to build the Tamiami Trail. Miami boosters were ecstatic about the bond approval. The day after the vote, the Miami Herald predicted that, within eighteen months, “the traveler may go over a splendid road from this city to Tampa.”
Surveyors had the Dade County portion of the highway laid out by March 1916, and on August 15, giant excavators started hacking westward toward the Dade-Lee county line.
In Miami, Dade County jailers kept a close eye on their most infamous prisoner, as John Ashley’s murder conviction awaited consideration by the Florida Supreme Court. On August 4, A. J. Rose, one of Ashley’s court-appointed attorneys, received a telegram from Tallahassee. It was from the clerk of the state Supreme Court. Ashley’s conviction had been reversed, and a new trial was ordered.
There was no explanation in the telegram for why the court had made this decision.
On September 14, Palm Beach County Sheriff George Baker, accompanied by a judge and a newspaper reporter, arrived in Miami to pick up Ashley. The old gentlemen’s agreement about no handcuffs was forgotten. Ashley left the jail handcuffed between two of the Palm Beach County delegation. He was taken back to West Palm Beach for his fourth trial for the death of Desoto Tiger.
The following afternoon, an Overland touring car with four riders rolled to a stop in front of the Bank of Homestead, about forty miles southwest of Miami.
Two men got out of the car and walked into the bank. One of the men wrote a check for $10 to Thomas Dice, signed it Dan Wilson, and the two men stepped up to a teller’s window and presented the check.
The teller didn’t know the men and called the bank’s cashier over to take a look at the check. As the cashier was examining the check, the men each pulled out revolvers.
“Hands up, gentlemen,” one of them said. “We have been in the Glades long enough.”
The men left with all of the cash in the bank—about $6,500. They headed west in the Overland—toward the Everglades.
For the next two weeks, the robbers fought a running gun battle with a posse that pursued them through the Everglades and into the Florida Keys. Three members of the posse were killed by “friendly fire” from other posse members in a shoot-out with the bandits on the morning of Sunday, September 17. But by October 2, two of the robbers were dead and the other two were in jail. There were reports that Kid Lowe, who was still wanted for the Bank of Stuart holdup, had planned the Homestead stickup.
John Ashley sat in the Palm Beach County Jail for two months until the date for his fourth trial arrived in November. But apparently no one saw any point in putting him on trial again for murder in a county where one previous trial had ended in a hung jury, and a jury couldn’t even be seated for a second trial. Prosecutors agreed to drop the murder charge if Ashley would plead guilty to robbing the Bank of Stuart in February 1915.
He was sentenced to seventeen years in the Florida State Prison in Raiford, about forty miles north of Gainesville.
In early 1917, Tamiami Trail boosters got a jolt of reality about how difficult it was going to be to push a highway through the Everglades. On February 10, Miami engineer John W. King, his son, John Jr., and eighteen-year-old William Catlow Jr. left Miami to survey land that had recently been purchased from the state for the Trail’s right-of-way. They thought it would take them about two weeks to work their way through the Glades to the Gulf Coast.
By late February, they hadn’t reached their destination, nor had they been heard from since they left Miami. On February 27, two experienced Everglades guides—a trapper and a Seminole Indian—went looking for the group.
Other search parties joined the hunt, but after more than a week, the three missing surveyors still hadn’t been found. On March 9, aviator Phil Rader and surveyor Burt Tubbs took off in a Curtiss military biplane and flew over the Everglades. It was a risky flight. Pilots had learned to avoid flying over the Everglades because of treacherous air currents over the vast swamp that could cause planes to suddenly drop hundreds, or thousands, of feet.
Rader pushed his plane to an altitude of 14,000 feet—a record for that time—partly to add a margin of safety in case he encountered a sudden down-draft, partly so that he and his passenger could see a bigger expanse of land. They saw a few people moving through the Glades, but they turned out to be search parties.
King and his two young companions were indeed having a rough time. The story of their trek through the Glades became the subject of an eight-part series by writer W. Livingston Larned that was published in 1918 in Forest and Stream magazine, a popular mass-circulation magazine that included among its contributors former president Theodore Roosevelt.
The elder King badly miscalculated what it would take to cross the formidable Everglades. He was “fairly familiar” with the outer edge of the Glades, and had not expected any major problems, Larned wrote.
But the interior of the great swamp was far different from what King had anticipated—impassable in some places, bewildering in others, and always eerily quiet, despite the obvious presence of so much wildlife.
“It seems past belief that, almost within hearing of Miami’s church bells, we should thus face absolute helplessness,” King wrote in the diary that formed the basis for Larned’s stories. “My faith in my own knowledge of the area is beginning to weaken.”
The story of the men lost in the Everglades made national headlines, and raised such concern for their safety that a group of Miami spiritualists offered their assistance in finding the lost exploration party. And J. F. Jaudon, for whom King was doing the exploration, seriously considered taking them up on their offer.
Even when the group was almost within sight of their Gulf Coast objective, they couldn’t find a path through the final stretch of the Glades. They could see distant waterspouts that occasionally formed over the Gulf of Mexico, but could not find a way out. They were weak and disoriented from hunger, and King began to wonder if they’d make it.
Finally, on March 14, a telegram arrived from Key West for J. F. Jaudon in Miami. The three missing men had made it to the mouth of the Shark River on the Gulf Coast, near the southwest tip of the peninsula. There, they’d come across a small processing operation owned by the Manetto Company, which extracted tannic acid from palmetto trees. The company’s superintendent had taken them by boat to Key West—the closest town—so they could tell the world that they were safe.
Suddenly the Miami Herald’s prediction about pushing a road through a couple hundred miles or so of the Everglades in eighteen months seemed a little optimistic.
John Ashley was back to his old tricks at the Florida State Prison in Raiford. He was behaving like a prisoner who sincerely wanted to mend his ways and hasten his return as a productive member of society. Prison officials noticed his exemplary behavior, and soon he was rewarded. In March 1918 he was transferred from Raiford to a prison work camp in Milligan, in the western Florida Panhandle, about fifty miles east of Pensacola.
Ashley was assigned to a chain gang. Every day, he and other prisoners, wearing pants with broad, alternating black-and-white horizontal stripes, climbed into what essentially was a cage on wheels and were taken to a site where they did manual labor on roads.
For three months, Ashley did his job, swinging picks and pushing shovels. But summers in the Florida Panhandle can be stunningly hot. And he was getting homesick again. He decided he’d had enough, and on July 11, 1918, he and another prisoner slipped away from the chain gang.
The western Panhandle was a long way from Ashley’s home, but somehow, he made it back to his familiar haunts down on the peninsula south of Stuart, and soon he was again spending most of his time in the Everglades. He found a new occupation: He and his father were operating three moonshine stills in the Glades.
And there was romance in John Ashley’s life.
Laura Upthegrove was not a delicate, feminine beauty. Author Hix C. Stuart described her as an “Amazon” who never left home without her .38 caliber revolver.
“There was nothing striking in Laura’s appearance to which might be attributed John’s devotion,” Stuart wrote. “Dark, unkempt hair, a tawny weather-beaten complexion, prominent cheekbones, squinting yet sharp black eyes, and generally untidy in appearance; there was nothing attractive about Laura,” Stuart wrote.
Yet Laura and John had magic moments together. An undated photo of the two shows a happy couple obviously in love and posing cheek to cheek for the camera against the backdrop of the Florida wilderness. Ashley, a few inches taller, stands behind Laura, his arms wrapped around her neck and shoulders. He’s wearing a white shirt, dark slacks, and what appears to be an army garrison cap. Laura, buxom and beaming at the camera, is dressed in women’s outdoor clothing of the late 1910s—a drab dark long coat and calf-length skirt, high-top shoes, and dark leggings. She’s holding on to John’s forearms.
Taken out of context, they appear to be merely a young couple very much in love instead of two desperadoes who would spend the rest of their brief lives on the run.
While dreamers were telling themselves that spanning the Everglades with a highway would be no big deal, and lawmen in southern Florida were spending a lot of their time seeking members of the Ashley clan in that vast swamp, world events were inexorably dragging the United States into the war raging in Europe.
Americans’ ire had been roused in May 1915 when a German submarine torpedoed the British passenger liner Lusitania, killing 1,198 people, including Americans. Germany, however, had realized what a potent weapon its undersea boats were, and was reluctant to curtail its attacks on Allied ships, regardless of whether they were warships. Even the Lusitania had been carrying war supplies along with its passengers, making it a legitimate target of war as far as Germany was concerned.
In March 1916, a German sub torpedoed a French passenger liner in the English Channel. No one was killed, but among the injured were a few Americans.
President Wilson warned Germany that the United States would cut its diplomatic ties with Germany if they continued to attack civilian shipping, and Germany responded by saying its submarines would not sink merchant ships without warning and would allow passengers and crew to abandon ship before sinking it.
President Wilson continued his efforts to mediate a peace between the Allies and the Central Powers, but German leaders had little interest in the negotiations because they thought they could eventually win the war outright rather than settle for a negotiated peace. Even the threat of American intervention didn’t concern them because they thought they could win the war before American troops were ready for combat.
In January 1917, Germany announced that it was lifting the restrictions it had imposed on its U-boats and would resume “unrestricted submarine warfare.” The United States severed diplomatic ties with Germany, and in March 1917 German subs sank five American merchant ships.
Then came the ultimate German insult to the United States. British intelligence agents intercepted a message circulating among some German officials suggesting that if America declared war on Germany, Germany should seek an alliance with Mexico. The inducement for Mexico to form this alliance would be the opportunity to recover the territory it had lost in its war with the United States from 1846 to 1848—territory that had become the states of Texas, New Mexico, and Arizona.
President Wilson released the message to American newspapers, and the nation was infuriated.
Former secretary of state William Jennings Bryan was in Miami in the months leading up to the US entry into the war. He was horrified that the United States was being dragged into a conflict that, he would later say, was caused by the same science that “manufactured poisonous gasses to suffocate soldiers” and was preaching “that man has a brute ancestry,” and eliminated “the miraculous and the supernatural from the Bible.”
Bryan rushed to Washington, DC, hoping to head off the move to war. But there was nothing he could do. On April 4, 1917, the United States declared war on Germany. Bryan had lost his bid to preserve peace, but he promptly sent a note to President Wilson telling him that he would do whatever he could to help the war effort.
Congress approved a draft that eventually would require all men between the ages of eighteen and forty-five to register for military service. Before World War I ended, about 2.8 million American men had been drafted.
One forty-five-year-old man who didn’t have to worry about the draft was an out-of-work architect named Addison Mizner. Suffering from a leg injury that wouldn’t heal, Mizner was shivering through the winter of 1917–18 in Port Washington, New York, overlooking Manhasset Bay on Long Island’s North Shore. The winter was made more miserable by a coal miners’ strike, leaving heating fuel very scarce.
Through a mutual friend, Mizner happened to meet Paris Singer, heir to a portion of the Singer Sewing Machine Company fortune that had been amassed by his father, Isaac Singer.
Paris Singer and Mizner quickly became friends, and Singer’s personal nurse suggested that Mizner’s leg would benefit from warmth and sunshine. So in January 1918 Mizner, Singer, and the nurse boarded a southbound Florida East Coast Railway train in New York City.
Mizner’s good health returned in the warm Florida winter, and he started designing a hospital that Singer wanted to build in Palm Beach for convalescing American soldiers returning from World War I. Soon, the jobless architect who had been shivering and suffering from a gimpy leg in a chilly Long Island apartment would become the toast of Palm Beach. The Roaring Twenties were just around the corner, and nowhere would they roar louder than in Florida.