Hundreds of miles away from Virginia, John Wilkes Booth was on a mission. Ostensibly going to Canada to enhance his theatrical wardrobe, Booth visited the unofficial headquarters for the Confederate Secret Service, the St. Lawrence Hall Hotel in Montreal, and checked into room number 150 on October 18.1
The twenty-six-year-old, a popular stage actor from a family of actors, was described by some as the “handsomest man in America.” Booth led a double life. His sister kept a secret memoir that was published upon her death. In it, she described her brother as “a spy, a blockade-runner, a rebel! … He has been from childhood, an ardent lover of the South and her policy.”2 Renowned for his keen mind and charisma, John Wilkes Booth was not a madman.
During the time of Booth’s stay, Confederate saboteurs had sallied out of their lair in Canada on October 19 to raid the town of St. Albans, Vermont, and hold up three banks, making off with over $200,000. The personnel and plans for the raid flowed from Montreal and George Sanders and company. One of the raid’s goals was to create an incident that would draw the British, who had Southern sympathies, into the war on the side of the Confederacy. They also hoped to force the Union to place more troops on the northern border to guard against future raids. The Confederates almost succeeded in creating an international incident when a local posse of Northern townspeople pursued the men who fled to Canada. Instead, Canadian authorities rounded up approximately a dozen raiders and recovered and returned over $80,000 of the stolen money.
After the raid, Sanders, who ascribed to the “theory of the dagger” and was a proponent of political assassinations, checked into room 169, just down the hall from Booth. Three credible eyewitnesses saw the two men together. One of them later recalled under oath, “They were talking confidentially, and drinking together. I saw them go into Dowley’s [the hotel bar] and have a drink together.”3
According to St. Lawrence Hall’s guest book, another crucial Confederate Secret Service operative checked in during Booth’s stay: John Harrison Surratt.4 He frequently stayed at the hotel; the guest book and arrival book have entries under his name and various aliases more than a dozen times. Only twenty when the war broke out, the divinity student abandoned his studies for the priesthood and became a Confederate courier and spy. Upon his father’s death, he assumed the role of postmaster and innkeeper of Surratt’s Tavern in Clinton, Maryland. His mother, Mary, had a boarding house in Washington, DC. Both destinations were safe houses for the Confederate Secret Service. Surratt would emerge as an essential member of Booth’s team and one of the South’s most significant operators.
Spy vixen Sarah Antoinette Slater often accompanied Surratt. The black-eyed, fair-complexioned, slim twentysomething5 got bored sitting around waiting for her husband to return from the war, so she volunteered for Secret Service work and was tied to some of their most important missions. Months later, Slater helped rescue the St. Albans raiders who had been rounded up by Canadian authorities. Often wearing a veil and speaking perfect French, she covertly carried papers from Richmond stating the men were not criminals but agents acting on behalf of their government, which halted their extradition to the United States. Adopting various aliases, among them Kate Brown and Kate Thompson, and referred to as the “the French Woman,” Slater captured the attention of those around her; Surratt confided to one man that he had “woman on the brain.”6
Booth’s diary revealed what they were planning. “For six months we had worked to capture [Lincoln],”7 Booth wrote in early April 1865. His diary entry placed the origins of Booth’s planning in Montreal in October and explained the plans to capture versus kill. Capturing Lincoln had advantages over assassination: the president could be used as political leverage in negotiations. Seizing the leader of the Union could destabilize Federal operations and war plans. After the Dahlgren Raid, Federal house burnings, and advancement toward total war, Lincoln had become a more palatable military target, since the Federals had planned to decapitate Confederate leadership during the Dahlgren Raid.
Confederates and Mosby demonstrated expertise in the capture of high-value targets, such as snaring General Stoughton. And Lincoln’s personal security remained surprisingly lax, as he often traveled with only a small escort. The Rangers could provide security for the capture team through hostile territory and bring Lincoln and the team to the safety of Richmond.
Parallel to the unfolding operation involving Booth, the Confederate Secret Service had another team also looking at kidnapping Lincoln. It is unclear whether this was an operation occurring concurrently or perhaps a feasibility group under the command of Captain Thomas Nelson Conrad. Confederate topographic experts and mapmakers went to work to examine egress routes from Washington to Richmond. Confederate secretary of war James Seddon cut orders in September that “Lt. Col. Mosby and Lieutenant Cawood are hereby directed to facilitate the movements of Captain Conrad.”8
A preacher and principal at Georgetown Institute, Conrad revealed his loyalties in 1861 when he ordered a band to play “Dixie” at commencement. Federal authorities soon arrested Conrad and threw him into Washington’s Capitol Prison but later released the fiery preacher in a prisoner exchange. Joining J. E. B. Stuart’s cavalry, Conrad took on the dangerous occupation of scout but never shed his religious calling. He assumed the role of chaplain. At the end of September 1864, the preacher spy infiltrated back into Washington, where he went to work for the Confederate Secret Service and was given $500 in gold, which Jefferson Davis authorized from Secret Service funds via Request No. 47.9 “I had reached Washington safely and begun to reconnoiter the White House.… I had to ascertain Mr. Lincoln’s customary movements.” At Lafayette Park, “only a stone’s throw from the White House,” Conrad observed for days: “Officials’ ingress and egress, noting about what hours of the day he might venture forth, size of the accompanying escort if any: and all other details.… We had to determine at what point it would be most expedient to capture the carriage and take possession of Mr. Lincoln; and then whether to move with him through Maryland to the lower Potomac and cross or the upper Potomac and deliver the prisoner to Mosby’s Confederacy for transportation to Richmond. To secure the points necessary for reaching a proper conclusion about all these things, required days of careful work and observation.… Having scouted the country pretty thoroughly … we finally concluded to take the lower Potomac route.”10
Testing the feasibility of this route became a priority. Months later, following the assassination, Booth would take the same route to escape from Washington and into Virginia. The path involved moving from Washington through southern Maryland using covert lines established by the Confederate Secret Service, crossing the Potomac, landing near Mathias Point, and traversing a peninsula known as the Northern Neck to the safety of Richmond. The Confederate Secret Service signals officer in the Northern Neck ordered to work with Mosby and Conrad was Lieutenant Charles Cawood. Mosby also had two Secret Service Signal Corps personnel assigned to his command.11
During this time frame, Mosby conducted a raid that, while not stated, was likely intended to test whether taking Lincoln across the lower Potomac would work. Mosby tapped Walter Bowie, one of his best Rangers, who was from a distinguished Prince William County family and knew the area like the back of his hand. Bowie also had ties to the Confederate Secret Service. The Scout led a band of twenty-five Rangers through the Northern Neck to Mathias Point, with the ostensible, likely bogus, cover story of aiming to capture the governor of Maryland. Their route of egress makes little sense for capturing the governor in Annapolis, which would have been easier to accomplish from the north. After capturing over a dozen Union soldiers and horses, Bowie’s men moved to Sandy Springs, a few miles from Rockville. Here a group of citizens and Union cavalry tracked them down and shot and mortally wounded Bowie as most of the remainder of his team escaped to Mosby’s Confederacy.
Booth fit right in at St. Lawrence Hall. As one witness, John Deveney, later swore under oath, “[Booth] was then in company with Sanders, Thompson, and others of that class. He seemed well received by these men and was on familiar and intimate terms with them.”12
Booth also racked and broke balls in the billiards room next to Dooley’s Bar. Drinks flowed freely as the game unfolded. Politics swirled in the air, and Booth is said to have exclaimed, “It made d—d little difference [who was elected], head or tail—Abe’s contract was near up, and whether elected or not, he would get his goose cooked.” Later, Booth boasted, “Do you know I have the sharpest play laid out ever done in America? I can bag the biggest game this side of—. You’ll hear of a double carom one of these days.”13
An eyewitness under oath later testified that, before he departed Canada, Booth went to the Ontario Bank, deposited money, and obtained a bill of exchange that could be cashed at other banks. The teller believed Booth might have been introduced to a “Mr. P. Martin,” a known Confederate agent with expert knowledge of the Confederate secret routes in southern Maryland. Martin also provided Booth with a Secret Service letter of introduction to contacts in southern Maryland, the “Doctor’s Courier Line,” that included ardent Southern operative Dr. Samuel Mudd, men who would abet Booth and his team in their flight from Washington to Maryland and across the Potomac to Virginia. The Secret Service’s underground lines in southern Maryland were essential to Booth’s mission. When the assassination option was introduced is not known, but the Confederates’ plans for kidnapping the president, and perhaps a deadlier operation, moved forward. During Booth’s stay, George Sanders proclaimed to a London-based Daily Telegraph correspondent that the Confederate Secret Service would conduct covert missions that “would make the world shudder.”14
The Confederate Secret Service planned to roll out a war of terror in the North from Montreal in conjunction with the kidnapping plot. The organization teemed with novel and groundbreaking ideas on how to survive the war and kill Yankees. One plot involved biological warfare. Within the group, Dr. Luke Pryor Blackburn, an expert on infectious diseases, gathered bales of infected clothing from yellow fever patients who died in Bermuda that he planned to distribute in Northern cities. The Confederate Secret Service plotted to poison New York’s water supply in another deadly operation. Neither operation got too far beyond the planning phase.
After spending nearly ten days in Montreal, Booth traveled by train to New York City, which was teeming with Confederate operatives. He would visit the city a dozen times, presumably meeting his Confederate handlers. There, Booth stocked up on weapons, ammo, and two pairs of handcuffs. He undoubtedly had help from the Confederate Secret Service to obtain two Spencer carbines, a cutting-edge weapon for the time.
Among other shadowy characters, the actor met with his good friend and fellow actor Samuel Knapp Chester. “After considerable conversation,” Booth attempted to enlist him in the plot to kidnap the president. “He finally opened the whole affair to him and stated there was a plot to kidnap the president and cabinet and take them to Richmond; and there were 50 to a hundred engaged in the plot and they have all taken the oath of secrecy, and that the plot was completed.”15 Here, Booth revealed the extent of the plot and its size; this was not a small group of conspirators. Booth promised Chester thousands of dollars for his involvement. When Chester demurred, Booth threatened to kill him if he went to the authorities, claiming he carried a derringer pistol to shoot anyone who betrayed him.
The clandestine organization also had operatives in place to burn New York to the ground. Initially scheduled to occur before the election, the plan to burn the city was delayed until November 25, the day after Thanksgiving; President Lincoln in 1863 had officially proclaimed the fourth Thursday of November a national day of thanks. Following the plot hatched in Montreal, eight operatives set fire to nineteen hotels throughout the city in addition to P. T. Barnum’s Museum. They rented rooms and then doused the mattresses with scores of bottles of “Greek fire,” a supposedly highly flammable liquid mixed by a sympathetic chemist. However, the Greek fire proved more difficult to ignite than they expected; simple matches would have been more effective. Moreover, many operatives failed to leave the windows of their hotel rooms open to feed oxygen to the flames.
Local authorities quickly recognized the fires as a Confederate plot and miraculously deployed fire departments and local citizens to douse the flames. Barnum’s museum, with its hay for the animals, proved their biggest challenge. As New Yorkers doused the flames, the perpetrators escaped back to their Confederate headquarters in St. Lawrence Hall. Only one arsonist was later captured in February 1865.
The operation to capture the president moved to the next phase: assembling an action team of operatives including John Surratt and John Wilkes Booth, as well as one of Mosby’s best Rangers.