Day after day District Attorney Miles McDonald’s rookies continued to raid bookmaking joints across Brooklyn; many of those arrested in the raids then received subpoenas to testify behind the twin smoked-glass doors of Room 405 of the Brooklyn County Courts Building. In that room twenty-two grand jurors—among them a former suffragist who had once campaigned for the right of women to serve on grand juries—sat for hours on end as a parade of witnesses took the stand. The grand jury heard testimony from policemen and bookmakers alike; bankers testified about the accounts of police officers suspected of receiving bribes, while representatives of brokerage houses detailed the officers’ stock trades. McDonald’s investigators, reported The Brooklyn Daily Eagle, were edging ever closer to a “bookmaking ring whose ramifications are reported to extend high into the borough’s social and political levels”; they were “hot on the trail” of “a top borough racketeer with choice political connections.”
Miles McDonald had not yet found the elusive Mr. G.
In April, rookies from McDonald’s squad had raided a restaurant in the Bay Ridge section of Brooklyn and arrested the owners, Salvatore and Thomas Starace, for bookmaking. The Staraces indignantly protested that they “had paid the cops regularly”; the brothers refused to say whom exactly they had been paying off, but several policemen from the local precinct were subsequently called to testify before the grand jury. One of them was Captain John Flynn, who explained under questioning that he had heard of bookmaking going on in the Staraces’ restaurant and sent a uniformed officer to investigate, but the officer found no evidence. After his testimony, Flynn was excused, and he was not required to return.
Three weeks later Captain Flynn checked in for work at the precinct house; in the captain’s room he lay down on the daybed, pulled out his service revolver, and shot himself in the right temple.
Flynn left a note denying that his suicide was related to his testimony, but in police circles he was widely believed to be a casualty of the McDonald investigation. On the day of his funeral some six thousand police officers gathered at the funeral home in Queens where Captain Flynn, in a flag-draped coffin, received a Solemn Requiem Mass. At the end of the service a group of reporters clustered around the mayor to ask for his reaction. For days O’Dwyer had been saying privately that Flynn had been “hounded to death”; now he could not resist the impulse to use the occasion to inveigh against McDonald’s investigation. “Nobody had the guts to say that Johnny Flynn was a clean man,” answered the mayor, “but six thousand policemen walked by his children to tell them so. I’m not opposed to the gambling investigation in Brooklyn. I have aided it when asked. But I am opposed to witch hunts and the war of nerves made popular by Hitler.”
O’Dwyer believed that linking McDonald with Flynn’s death would, as he assured aides, “finish that knucklehead who used to work for me,” but he had miscalculated the impact of his words. Raising the dark specter of Hitler only five years after the end of the Second World War, in a city still deeply traumatized by the Holocaust, seemed shockingly inappropriate and only intensified the widely held suspicion that Bill-O was losing his political touch, losing the ability, finely honed over two decades in public life, to understand and express the problems and desires of everyday New Yorkers—for while the people of the city were not especially concerned about the activities of bookmakers, they were concerned about the idea of police officers accepting bribes to protect those bookmakers. In his autobiography O’Dwyer acknowledged the error: “It may have been a justifiable label,” he wrote, “but it was not good politics to say so, and I paid the price for the rash statement.”
He was doing what he could in those months to maintain his rapport with the people of New York, the easy give-and-take that cheered him and gave him hope for the future. Often on sunny Sundays he would wander onto the lawn of Gracie Mansion and chat with neighbors through the bars of the fence; sometimes he and Sloan Simpson would stroll hand in hand through nearby Carl Schurz Park, the mayor tipping his homburg to those who passed by. O’Dwyer had also begun appearing on a new television show called At the Mayor’s Desk, broadcast every other Thursday night. For half an hour he and various government officials would sit in his City Hall office and informally discuss the problems of New York, but as the New Yorker correspondent Philip Hamburger noted, “the Mayor himself is unquestionably the star of the show. Not only is he a fine figure of a man but he could give many television actors a lesson or two in how to behave in front of the cameras.”
All of the great deeds he planned for his second term and that he so loved to talk about on his show—the juvenile aid initiatives, the water pollution control programs, the new highways and public housing complexes—were being overtaken by the bookmaking scandal in Brooklyn, a vast and splendid landscape dimmed by a single dark cloud. The mayor had always maintained amicable relations with the press; now he complained incessantly about the treatment he was receiving in the papers, refusing to speak to reporters for days at a time. He himself seemed unable to let go of thoughts of the burgeoning scandal, even on the most unexpected occasions. During a ceremony welcoming Australian prime minister Robert Menzies to City Hall, he praised the prime minister’s “ready wit and sense of humor,” then could not refrain from adding, “I am sure, sir, that you will agree that a sense of humor saves a man in public life from worrying over the machinations of his political enemies.” For New Yorkers it was discomfiting to see their mayor, long known for his charm and geniality, appearing to brood in public about his “enemies.”
At the end of July, Samuel Leibowitz, the judge overseeing the Brooklyn grand jury, summoned the mayor to what the newspapers termed a “peace parley.” Accompanied by Police Commissioner O’Brien and several top aides, Mayor O’Dwyer drove to Brooklyn to meet Judge Leibowitz and the foreman and assistant foreman of the grand jury. Sitting down with the visitors in his chambers, the judge reminded them that his job was to ensure that the grand jury’s work continued free from interference. “It seems to me,” he told the mayor, “that you and other officials in this city ought to work together” rather than “engage in acrimonious newspaper debate.” He had just released forty-one pages of grand jury testimony, he said, which demonstrated conclusively that Captain Flynn had been treated with the utmost respect and consideration and that his honesty had not been impugned in any way.
For his part, Mayor O’Dwyer affirmed that he had always tried to aid the inquiry—had even offered his top investigator to lead it—but that all his efforts to bring a sense of objectivity and professionalism had been thwarted by the district attorney. After half an hour the police officials departed; Samuel Leibowitz had always been known for the directness of his speech, and now, with the policemen gone, he loosened his tongue, telling the mayor that he had been acting in a partisan and intemperate manner, and then he went even further, suggesting to O’Dwyer that his usefulness as a mayor had ended and that it was in his interest and the interest of the city for him to leave office as quickly and as gracefully as possible.
Afterward, reporters were waiting for the mayor back at City Hall. “I went to Brooklyn,” O’Dwyer told them, “to give Judge Leibowitz and the grand jury assurance that there would be complete cooperation from the mayor and the Police Department.”
“Was there any criticism of the district attorney?” asked one of the reporters.
O’Dwyer hesitated for a moment, then said only: “No comment.”
“Do you still think that Mr. McDonald is conducting a witch hunt?”
“No comment.”
“Do you still think the grand jury is pursuing Hitler tactics?”
“I never said that, and I told the grand jury that today.”
Despite Judge Leibowitz’s sterling reputation in the city, O’Dwyer deeply distrusted him, considering him a headline chaser and a political climber. Still, he considered it a remarkable day when a County Court judge felt free to tell the mayor of the City of New York that he should resign. Rumors were flying about what the Brooklyn grand jury was learning. They were zeroing in on the big man, it was said, the bookmaking kingpin with the political ties; there was talk that wiretaps conducted by McDonald’s squad had captured conversations between bookmakers and cops that included the names of New York City political officials—even that of the mayor. Years later he would write of that period, “I somehow felt things getting away from me.”
Late nights he often rambled around Gracie Mansion, worrying and brooding, the only one awake in the house other than the security detail, who dared not intrude on his privacy. Sloan was always urging him to attend the social functions for which he had less and less patience; she preferred to go out at night, escaping the tension that had begun to pervade the house. After returning from their Florida honeymoon she had set out to redecorate the mansion, hanging Irish paintings on loan from the Metropolitan Museum of Art, rearranging the living room so that more people could sit in one area for after-dinner conversation. Of late, friends had begun to remark on the wistfulness that had crept into his talk, the stories of his boyhood in Bohola. It was a little world of bogs and stone huts and star-filled nights, where he had no dreams greater than to become a village schoolteacher like his parents; his father, though, had wanted him to test his mettle in America. “In the USA,” he said, “you’ll either be a bum or a man.” Now he lived in a colonial house overlooking the river, with pictures of Irish scenes on the wall; it was a beautiful home, far better than any other he would ever know, and he would be sorry when he had to leave it.
One night in August, reading by lamplight in his study, he received a most unwelcome visitor.
Edward J. Flynn had run the Bronx Democratic machine for the previous twenty-eight years. During that time the Bronx had not elected a single Republican official; a political candidate nominated by the local machine was such a shoo-in to be elected that he was said to be “in like Flynn.”*
Ed Flynn confounded every stereotype of the urban party boss: He was patrician in manner, tall and silver haired, an avid horticulturalist with a taste for literature and fine art, likely the only political boss ever to have his memoir excerpted in the pages of The Atlantic Monthly. Introspective and aloof by nature, prone to bouts of melancholia, Flynn was uncomfortable in crowds, which for a big-city politician of the time was akin to a physician who recoils at the sight of blood. He abhorred back-slapping and glad-handing and rarely appeared at the benevolent association dinners and police smokers on which William O’Dwyer had built a career. He much preferred to spend time at his upstate farmhouse or the ranch where he bred racehorses, or pass the evening playing gin rummy or Russian bank at home with his wife. Flynn maintained his control of the party machinery in large part through the adroit dispensation of patronage—including jobs for leaders of the local Republican Party, as he understood that this would reduce the incentive for genuine opposition. Though he was a strong supporter of Franklin Roosevelt, he was continually frustrated by New Dealers (“amateur politicians,” in his disdainful phrase) who were willing to provide patronage even to those not connected to party organizations; Flynn firmly believed that politics was important enough that, like medicine or engineering or the law, it should be left to the professionals.
Under Flynn’s command the Bronx was, by percentage, the most heavily Democratic territory anywhere north of the Mason-Dixon Line, reliably providing huge numbers of votes to elect Democratic officials statewide and deliver the state in national elections. In 1940 he had been named chairman of the Democratic National Committee, and he had served as the campaign manager for Roosevelt’s 1940 and 1944 presidential campaigns. Along with the Manhattan Tammany Hall chieftain he was also responsible for putting together the Democratic ticket in New York City elections, negotiating various constituencies to create an optimally balanced ballot line, with candidates representing the Democratic strongholds of Manhattan, Brooklyn, and the Bronx, and ideally including at least one Irishman, one Italian, and one Jew. He was the consummate political professional, able to read even the gentlest of political winds, and it was not hard for him to see how damaged William O’Dwyer had become; Flynn recognized that the McDonald investigation was going to expose serious public graft and police corruption, and he believed it would be prudent for the Democratic Party to remove those tainted by the bookmaking scandal before the voters next went to the polls.
Furthermore, a New York gubernatorial election was scheduled for that coming November. The Republican incumbent, Thomas E. Dewey, was a popular governor, and the only way he might be defeated was to dramatically increase Democratic turnout, especially in New York City—and the most effective way to increase the city’s turnout was to hold a mayoral election on the same day. O’Dwyer, however, had only just been reelected, and the seat would not open up again until 1953. And so, Flynn reasoned, it would be necessary to hold a special mayoral election that coming November, with a new field of candidates, and that would mean persuading O’Dwyer to resign.
So Ed Flynn traveled to the White House, where he met with President Harry S. Truman in the Oval Office. In 1944, when Franklin Roosevelt wanted Truman to be nominated as vice president, it was Flynn to whom he entrusted the important and delicate task of convincing party leaders around the country to support the choice; Truman had not forgotten the service, and after he succeeded Roosevelt he retained Flynn in the informal position of the president’s man in New York. Now Flynn explained to President Truman that for the good of the party, Bill-O had to be gotten rid of.
Flynn’s proposition to Truman had an almost fiendish cleverness: In 1948 O’Dwyer had publicly suggested that Truman should be replaced at the top of the Democratic ticket, because, he argued, Truman could not beat the Republican presidential nominee, Thomas Dewey. The notion of increasing Democratic turnout in the gubernatorial election by means of a special New York City mayoral election thus presented Truman with the gratifying prospect of dispensing with both O’Dwyer and Dewey in a single blow.
As it happened, the president had recently received the resignation of the career diplomat Walter C. Thurston, who had been serving as U.S. ambassador to Mexico. He would send O’Dwyer to Mexico, Truman told Flynn. There was just one problem: The ambassadorial position paid only $25,000 a year—would O’Dwyer be willing to take a $15,000-a-year pay cut?
“Don’t worry,” said Flynn. “He’ll take it.”
It was nearly midnight when Ed Flynn arrived at Gracie Mansion. O’Dwyer himself answered the door; together he and Flynn walked through the grand foyer and into the living room. Earlier in the evening the mayor had attended a political dinner, and he was still wearing his black dinner jacket, with a starched white shirt beneath. Flynn was dressed, as he always was, in an expensive, finely cut suit with a boutonniere in the lapel and a flowered Charvet tie. He settled into an easy chair as O’Dwyer poured them a pair of whiskeys.
The two men sat contemplatively with their drinks; from beyond the darkened window they could hear the mournful call of the foghorns on the river. After a while Flynn said, “I guess you know why I’m here, Bill.”
“Yeah,” O’Dwyer replied in a quiet voice. The lamp above his head had whitened his graying hair, so that he appeared unexpectedly old.
“Well, how do you feel about it?”
“How can I feel?” The indignation of his tone seemed briefly to energize him, and for a moment it was as though he were back on the campaign stump reciting his own accomplishments, as he reminded Flynn of the years of service he had given New York, the countless favors he had provided for their friends in the party.
“It’s pretty late, Bill,” Flynn interrupted. “Now, look—we want you out just as soon as possible. Maybe within two weeks.”
With that O’Dwyer seemed to crumple a bit, and for a long while he just sat silently, staring at the carpet. Then he raised his head and said, “What have they got for me?”
“You’re lucky,” Flynn replied. “I’ve been to see the president. He says, if nothing goes wrong before then, you can be ambassador to Mexico.”
O’Dwyer sighed. He had spent so many nights strolling the long porch outside, even snowy nights, stormy nights, just marveling at the lights of the city shimmering in the distance. He would, he knew, never get New York out of his head. At last he said faintly, “All right.”
“Very good,” said Flynn. “You’ll be hearing from me.” He rose and left the room, leaving the mayor sitting alone in the lamplight.
At six o’clock on the evening of August 14, Mayor William O’Dwyer boarded a Pennsylvania Railroad express train bound for Washington, D.C. No explanation was given for the sudden trip, though it was generally understood that he would be meeting the next day with President Truman at the White House. As it turned out, they met for no more than twenty minutes; afterward came an announcement from the president’s secretary that Mayor O’Dwyer would resign his office at the end of the month and would then be appointed United States ambassador to Mexico. “I had a conversation with the president that made up my mind,” O’Dwyer explained to reporters in the drawing room of the train returning home. “What that conversation was I am not going to disclose.”
The next day O’Dwyer attended a meeting of the city’s Board of Estimate at City Hall, the final such meeting he would oversee as presiding officer. In a voice choked with emotion he told those gathered in the chamber, “I am saying this morning my official goodbye to the city. I want you to remember that a city that took in an immigrant forty years ago, gave him every opportunity, and step by step honored him over and above his just deserts….” There the mayor’s voice broke, and he paused to wipe his eyes with a handkerchief. “We pray,” he continued after a moment, “that when we leave we will leave a city, state, and nation better for those who follow us. I haven’t words to say any more. I have tears, but you don’t want them.”
With that he resumed his seat, putting on his tortoiseshell reading glasses and lighting his curved-stem pipe. For the next hour, the Board of Estimate proceeded to hand out $116,000 worth of raises to various officials on the city’s payroll. The mayor’s two police chauffeurs were promoted to deputy police commissioner; his bodyguard, Detective Joseph Boyle—the man who had claimed that he’d accidentally started the fire in the mayor’s hospital suite—was likewise made a deputy police commissioner. Not surprisingly, the most prized appointment of all went to Bill-O’s closest aide, James Moran: He was named a commissioner of the city’s Board of Water Supply, a well-paying lifetime appointment and not subject to the discretion of future mayors. Moran’s only apparent qualification for the job was his career of service to William O’Dwyer. It was, reporters Norton Mockridge and Robert Prall noted in their book The Big Fix, “one of the most shocking appointments ever made by any mayor in the history of New York.”
On September 2, 1950, the city clerk received a letter bearing the official seal of the city. It read simply: “Dear Sir: I hereby resign as Mayor of the City of New York. Very truly yours, William O’Dwyer.”
Thirteen days later, Chief Investigator William Dahut and another detective burst into Room 1116 of the Towers Hotel in Brooklyn Heights. The room was furnished with richly upholstered chairs, thick carpeting, and gold brocade draperies, and it opened onto a terrace that commanded a magnificent view of New York Harbor. Though it was almost eleven o’clock in the morning, the room’s occupant, a paunchy young man with slicked-back black hair and manicured nails, was unshaven and wore only pajama bottoms.
“We’re from the district attorney’s office,” said Dahut, flashing his badge.
Harry Gross nodded. “I’ve been expecting you fellows for some time,” he said.