In the fall of 1949 the Democratic mayor of New York City, William O’Dwyer, the one hundredth mayor in the city’s history, would seem to have been riding high. On November 8 he had been reelected to a second term, a mandate given by the citizenry of New York for his policies of expansive government (“Government should permeate,” he liked to say, “it shouldn’t crush”) and the patronage jobs that he dispensed at a rate not seen since the glory days of Tammany Hall, the city’s venerable Democratic machine. Yet the mayor was deeply troubled. In his relatively brief but highly successful career as a politician, O’Dwyer had been driven by two conflicting forces: ambition and fear. Though he had long dreamed of occupying the city’s highest office, he had more than once tried to give it up when it was within his grasp, as if, historian Robert Caro observed, he was “desperately afraid of what the spotlight in which a mayor must walk might reveal when it shone on those shadowy places in his past.”
On the very day in 1945 that O’Dwyer received the Democratic nomination for mayor of New York, he had pleaded with party leaders to name him to a judgeship—for, by an arcane provision of New York electoral law, that was the only way the winner of a primary election could refuse the nomination. That request had gone unfulfilled; O’Dwyer won the mayoral election decisively and served out a successful first term.
Now, less than three weeks after his reelection and at the apex of his political power, he began to complain of dizziness and palpitations of the heart. On November 28, 1949, he checked in to Bellevue Hospital; there, in his hospital room, having not yet been sworn in for a second term, he wrote out and signed his letter of resignation.
William O’Dwyer (Bill-O, as he was known to his friends, and he had friends in every part of the city) was fifty-nine years old, still a handsome man, with broad shoulders and a ruddy face and a thatch of graying hair that set off the thick black eyebrows that were his most distinctive feature—other than his voice, which was exceptionally fine, deep and resonant and with just a trace of an Irish lilt. O’Dwyer’s was a classic New York success story. An immigrant from County Mayo, one of eleven children born to a pair of village schoolteachers, at the age of twenty he had arrived in the city with twenty-five dollars in his pocket and no clothes but the suit on his back. Eventually he found work as a plasterer’s helper; years later, as mayor, O’Dwyer would stand on the steps of City Hall and, gesturing up at the Woolworth Building towering across the street, say proudly, “It was with these hands that I helped erect that building. And so, for all time, I have left my mark on the city.”
He had always loved books (he quoted lavishly from Dante, Yeats, and Byron) and during his time in the construction trade he read Western novels to his fellow hod carriers on their lunch breaks; the other men, grateful for the diversion, didn’t realize that he was working on his pronunciation, trying to lose his thick brogue, which he understood was going to be an impediment to his success—he just didn’t yet know in what. After several years in construction he took a job as a bartender at the Vanderbilt Hotel, where he spent endless hours watching the customers, the wealthy and well-dressed whom he thought of as “the dainty people,” trying to figure out how to act like one of them; more important, while working at the Vanderbilt he fell in love with one of the hotel’s switchboard operators, Catherine Lenihan*—Kitty, she was called—who believed in him and gave him confidence when he had little, who persuaded him to take the civil service examination and become a policeman. Later, with Kitty’s encouragement, he enrolled in evening law school at Fordham University; in 1925 he passed the bar exam and went into private practice as a defense attorney.
In late 1932, Acting Mayor Joseph V. McKee appointed him magistrate; it was the lowest tier of judgeship but a platform from which a political career might be launched, and in those years O’Dwyer passed many evenings in Brooklyn’s fraternal lodges and the banquet rooms of the political clubhouses. Even then, Bill-O knew how to win over a crowd, with his swept-back hair and the expansive gestures of a Broadway idol, opening his arms wide as he spoke of how as a young man from a small Irish town he had fallen in love with the great hectic city of New York, where people from the four quarters of the earth lived together in peace and harmony—but how he also knew they could do better still, and he clasped his hands prayerfully to his chest as he called on the city to build better schools and playgrounds for its children, to clear slum housing and build new hospitals, his rich voice lowering in sorrow as he spoke of “the needy sick, those helpless ones.” No one could doubt O’Dwyer’s deep concern for the welfare of the poor and weak and newly arrived—they were, he felt, his own people—but it seemed just as clear that he was a man on the move. Among those who recognized the magistrate’s political talents was Frank V. Kelly, the Democratic leader of Brooklyn; after first maneuvering O’Dwyer’s appointment as a County Court judge, in 1939 Kelly put him forward as the Democratic candidate for district attorney, which in Brooklyn was tantamount to election.
Over the next two years O’Dwyer earned a citywide reputation as a crusading DA, obtaining eighty-seven murder convictions, including death sentences for seven members of Murder, Inc., Brooklyn’s ruthless gang of killers for hire, and in 1941 he ran as the Democratic candidate against Fiorello H. La Guardia—a feisty Republican progressive and one of the most popular mayors in the city’s history. Though O’Dwyer lost that race he kept the margin of victory to only six percentage points; it was clear to all observers that his political future in the city was still bright, and that he could very well return City Hall to the Democrats if he were to face an opponent less formidable than La Guardia.
When the Second World War broke out, O’Dwyer enlisted and was sent to Wright Field in Dayton, Ohio, eventually rising to the rank of brigadier general. In December 1942 he took time out from his military duties to travel to New York for a small cocktail party hosted by Frank Costello, the most powerful of the city’s underworld bosses, at his penthouse in the Majestic Apartments on Central Park West. Costello was a former bootlegger turned gambling czar who had now expanded his empire into legitimate businesses including oil and real estate, whose friendships with political officials and ability to dispense favors had earned him the respectful sobriquet “the Prime Minister.” He was a potent political force in the local Democratic Party, and Manhattan district leaders were regularly seen with him at the city’s most high-profile restaurants and nightclubs. “I know the leaders, know them well, and maybe they got a little confidence in me,” he said modestly. In 1949, Manhattan borough president Hugo Rogers summed up the situation concisely: “If Frank Costello wanted me,” he said, “he would send for me.”
William O’Dwyer in 1945, having just received the news that he had been elected mayor of New York. Associated Press
Some of those who knew about the penthouse meeting between the general and the mob boss would later say that it had been arranged in hopes of obtaining Costello’s support for O’Dwyer’s next mayoral campaign; O’Dwyer himself claimed that they had discussed only Army business, but he could never explain why, if that were the case, several Tammany leaders and political contributors were also in attendance that evening.
Fiorello La Guardia chose not to run for a fourth term in 1945, and this time William O’Dwyer received 57 percent of the vote and became the mayor of the City of New York. On New Year’s Day 1946 he was inaugurated in a festive ceremony at City Hall, joining with the Police Glee Club to sing “It’s a Great Day for the Irish.” In his inaugural address the new mayor struck a forward-looking note, speaking of the great responsibilities he felt in leading the city, the need to address problems left unattended during four years of war. After the swearing-in of his cabinet members, he was escorted to his new office as the glee club sang “For He’s a Jolly Good Fellow.”
Yet even as the city’s highest officeholder, Bill-O could not escape the rumors that he was operating in the service of forces more powerful than himself. Much of the gossip swirled around his closest aide, a shadowy figure named James J. Moran, who, it was whispered, ran the city from his office on the eleventh floor of the Municipal Building. One City Hall observer would later write that Moran “acted as though he owned O’Dwyer”; some who heard the two in conversation would say that they were never quite sure who was giving orders to whom.
Jim Moran was a colossus of a man, a tough, hulking redhead with a lantern jaw and hands like slabs of beef; he had a pink complexion, hooded eyes, and a deep crease on each side of his face that ran from his nose to his mouth, giving him the cobbled-together, slightly mechanical look of a ventriloquist’s dummy. Born into an Irish immigrant family in a rough section of Brooklyn, Moran had started out on the waterfront as a checker of cargo, but like O’Dwyer he studied at night and eventually took the civil service exam and became a legal stenographer and court attendant, a huge man in an ill-fitting uniform who was always available to do a favor for the attorneys and political functionaries who used the courthouse as their base of operations. Judge O’Dwyer, the newly appointed magistrate, seemed to appreciate how easily Moran moved through the world of the courthouse, trading favors and pulling strings, and he hired him as a special attendant. When O’Dwyer became the district attorney of Brooklyn he made Moran his chief of staff. By then Big Jim Moran was already understood to be the man to see if you needed something from Bill-O; he was, in the description of one observer, “as close to O’Dwyer as his shirt.”
As mayor, O’Dwyer appointed Moran first deputy fire commissioner, a position from which he could set into motion an audacious form of shakedown. The city’s building regulations required that oil burners and storage tanks pass inspection by a fire marshal before any new construction could be completed; shortly after taking office, Moran called in his senior-level inspection personnel and instructed them that in the future no oil burner permit would be issued until a private fee had been paid to the inspector. Moran provided a sliding scale of rates, from five dollars for a small one-family house all the way up to five hundred dollars for a factory or warehouse. This fee was to be paid whether or not the inspector found a violation; nor, if one actually was found, did Moran care if it was ever corrected. In issuing a permit the critical factor was simply that the inspector had received his payment—a portion of which, of course, was to find its way back to Jim Moran. Withholding an oil burner permit could hold up construction for weeks or months, a price that no developer was willing to pay; it was far cheaper and easier simply to fulfill the transaction, to hand over the bribe and receive the necessary permit, no questions asked. Nor would a developer who desired ever to build again in New York City see any gain in challenging a directive that, it would have been made clear, came straight from the mayor’s closest political adviser.
In 1949 the Republican mayoral candidate, Newbold Morris, had tried to make an issue of William O’Dwyer’s ties to party bosses and organized crime. Morris denounced O’Dwyer as “the mob’s man in City Hall,” releasing a list of 124 alleged bookmaking sites in the borough of Brooklyn alone. A descendant of an aristocratic family who had attended Groton and Yale, Morris could gain little traction with his charges, and for his part O’Dwyer did not deign to respond to them, saying simply, “There are more serious things for police to do than hunt bookmakers.”
O’Dwyer’s own campaign proclaimed that he was “Courageous, Reliable, Experienced,” those descriptives emblazoned alongside his smiling face on posters displayed all over town, and the incumbent seemed to be everywhere that fall, his Cadillac limousine screaming through the avenues as a motorcycle cop ahead cleared traffic, up the East River Drive from his home at Gracie Mansion to a campaign stop where the mayor would recount the illustrious history of the city: Reminding the audience of how in earlier days George Washington had commanded from Belview Mansion, on the very spot where Gracie Mansion now stood, and Alexander Hamilton had led rebel troops up a cow path called Broadway, noble forebears who had conquered the seemingly unconquerable, he clenched his fists and extended his arms, and before long his listeners were accompanying Lewis and Clark on their trek through the Northwest. “Over river and hill and plain and mountain,” he intoned, “under the winter’s blast and the summer sun”—and when that excursion was completed, Bill-O had somehow come back around again to New York, describing the 58 new schools, 42,000 units of public housing, 760 new subway cars, and 2,000 new buses he had provided for the city during his four years as mayor, and the money for municipal hospitals, and the swift and efficient snow removal during the blizzard of ’47.
His hair was grayer now, and shadows darkened under his eyes, but his posture was still ramrod straight, as if to remind his audience of his service in the Army during the war, and indeed, some of his supporters addressed him as “General.” His demeanor was commanding but unpretentious as he stood on the dais wearing one of the double-breasted suits that even now, as mayor, he bought off the rack (often smartened by a carnation in his lapel), with a loud patterned tie and the same style of comfortable thick-soled black oxfords that he had worn when he walked a beat on the streets of Brooklyn. What always came strongly across to his listeners was that unlike so many would-be reformers, he seemed genuinely to love this city and to know it inside and out, and those in the audience couldn’t help but recall, too, that the mayor’s heart had been broken when his wife passed away during his first year in office; that tragedy seemed to make his attention to their concerns even more affecting, and when his speech was over they invariably gathered around him—he was never one to deflect physical affection—patting his shoulder and clutching his arm as they pumped his hand, and then he murmured his apologies for his crowded schedule and he ducked out a side door and was back in his Cadillac heading somewhere else.
After many years of ill health, Kitty had succumbed to Parkinson’s disease in 1946. Her brief stay in Gracie Mansion had been filled with hardship and sadness, and her death, after thirty years of marriage, was the great sorrow of O’Dwyer’s life; even six months later he still broke down when he spoke in public of “Mrs. O’Dwyer.” He spent two years filling up his evenings with social and civic events, but in 1948 he met a fashion model from Dallas named Sloan Simpson and had soon taken up with her, the two of them regularly photographed attending a Broadway show or walking hand in hand in the park. When the mayor was going to marry Miss Simpson had become a preoccupation of the city’s papers, but she was twenty-seven years his junior and, as he would later write, “misgivings about a May-December marriage continued to haunt me.”
On the evening of November 28, 1949, he was almost overcome with dizziness, and he instructed his secretary to have his physician meet him at Gracie Mansion. When the doctor arrived he found O’Dwyer weak and trembling, barely coherent; he was sped by ambulance to Bellevue Hospital, where upon examination he was diagnosed as suffering from “almost complete nervous and physical exhaustion” compounded by “very definite heart strain.” The mayor was checked in to a three-room hospital suite, and over the following week he undertook a regimen of near-complete rest. He was often under mild sedation, but as the days went by he became increasingly depressed; finally, on Sunday afternoon, December 4, he resolved that he could no longer endure the burdens of the job, and he wrote out a letter of resignation for his secretary to type up. That afternoon he called James Moran and informed him that he had resigned as mayor; Moran told O’Dwyer to calm down and do nothing more until he got there.
Sometime around five o’clock Moran, red-faced with anger, stormed in as O’Dwyer lay in his hospital bed. Back and forth he stomped, his massive body seeming to fill up the entire room, pausing only to pound his fist on the dresser as he shouted at the mayor that he could not resign, would not resign, without first taking care of him, that he needed to be rewarded for his years of service. O’Dwyer shouted back that he very well could resign, no one could stop the mayor from resigning, and with a flourish he pulled out the resignation letter, typed and signed, from a drawer in the bedside table and brandished it at Moran. In a burst of fury Moran snatched the letter away and, taking a book of matches from his pocket, lit the paper and let it burn for a moment before dropping it into a metal wastepaper basket.
Sitting in an adjoining room, the mayor’s bodyguard, Detective Joseph Boyle, suddenly heard a startling cry: “It’s on fire!”
The resignation letter had ignited the other papers in the wastebasket and the room was quickly filling with smoke. Boyle rushed in and managed to extinguish the flames, but by then the smoke had gotten into the ventilation system, and in the corridor one of the nurses noticed it and called the hospital switchboard. In a matter of minutes, twenty New York City firemen arrayed in helmets, rubber coats, and boots were tromping through the corridors looking for the source of the smoke.
At the entrance to the mayor’s suite they were met by Detective Joseph Boyle. “What’s the trouble?” he asked.
“Smoke in the corridor,” said the battalion chief. “Any fire in here?”
“Nah,” the detective replied; he explained that he had been making toast in the suite’s kitchen when the phone rang, and since the mayor was asleep he ran to get the phone, and as he did he accidentally dropped a dish towel on the toaster and the end of it got burned a little. But everything was okay now, he assured the chief, so there was no need to investigate further. “Besides,” he added, “the mayor’s sound asleep in that room. We don’t want to wake him up.”
The firemen duly retreated, and the next day the city’s papers carried an amusing item about the little fire that had been caused by the spark from the dish towel.
“The mayor,” reported the Associated Press, “slept through it all.”
Mayor O’Dwyer checked out of the hospital a few days later and flew down to Florida for a long vacation. While there he held a press conference to announce that he was getting married, and in the coming days the city’s news pages were dominated by speculation about the details of the wedding, to be held December 20 in a Catholic church in the small Florida town of Stuart.
The sports pages, meanwhile, were full of stories about the surprising City College basketball team, which had now compiled six victories against only one defeat. On December 27, City was scheduled to play against the Bruins of UCLA. That afternoon Norm Mager passed the word: This was the game they owed the gamblers.