Until I read this article I had never heard of William O’ Dwyer.
William O’Dwyer was beloved by New York City.
So why did he abruptly leave office and head to Mexico?
William O’Dwyer was a decent man, or so many New Yorkers believed. After his first term as mayor of New York City, from 1945 to 1949, the Daily News called him “100 per cent honest,” while the New York Times proclaimed him to be a civic hero, alongside his predecessor, Fiorello La Guardia. A former cop turned Brooklyn prosecutor who helped send members of Murder, Inc. to the electric chair, O’Dwyer came into office facing challenges that would have made even an experienced mayor blanch—a tugboat workers strike, a looming transit strike and a shortage of city funds—and he solved them all. His landslide re-election in 1949 seemed to complete the story of the poetry-loving immigrant who arrived from Ireland with $25.35 in his pocket and became the mayor of America’s biggest and richest city.
A warmhearted man with blue-green eyes and thick graying hair, O’Dwyer soothed petitioners with a lilting Irish brogue. He was a study in contrasts: He wore white shirts with his black cop shoes, and could recite long stanzas from Yeats and Byron from memory, a New York version of Spencer Tracy’s handsome, gregarious Irish politician in The Last Hurrah (as the New York Times once noted). The mayor openly sympathized with what he called the little people. As a cop, he once shot and killed a man who raised a weapon at him; wracked with remorse, he then fed and educated the man’s son. When O’Dwyer’s wife died, after a long illness, the city mourned with him. When he met and married a fashion model from Texas named Sloane Simpson, who was more than 20 years his junior, no one begrudged the mayor his happiness. He was a surefire candidate for senator or maybe governor.
Yet only months into his second term, O’Dwyer’s reputation as a crime-fighter was coming undone. In December 1949, the Brooklyn district attorney, a squeaky-clean family man named Miles McDonald, began investigating a bookmaker named Harry Gross. In his effort to figure out how Gross could operate a $20 million betting operation without attracting the attention of law enforcement, McDonald uncovered a wide-ranging conspiracy that connected cops on the street to the highest levels of the New York City Police Department, who were connected in turn to the city’s most powerful politicians and crime bosses.
As newspaper headlines charted McDonald’s progress, more than 500 New York City policemen took early retirement rather than risk being called before the prosecutor’s grand jury. Seventy-seven officers were indicted, and the police commissioner and the chief inspector were booted from the force in a cloud of scandal and disgrace. McDonald’s investigation also zeroed in on James Moran, a silent, white-haired former cop who had accompanied O’Dwyer at every stage of his rise and now served as deputy fire commissioner. It seemed it was only a matter of time before charges would be filed against the mayor himself. Instead, at his moment of greatest peril, O’Dwyer found a protector in President Harry Truman—a man he didn’t know well, and who didn’t particularly like him. The reasons Truman protected O’Dwyer have never been adequately explained. “The O’Dwyer story is one of New York City’s more intriguing political mysteries,” Mike Wallace, the Pulitzer Prize-winning co-author of Gotham: A History of New York City to 1898, told me. “It would be great to know what actually happened.”
In order to understand what happened, who William O’Dwyer was, and why Harry Truman protected him, it is necessary to re-examine what we think we know about organized crime. Cozy working relationships between urban criminal organizations, big-city labor unions and the mid-20th-century Democratic Party were first exposed by Senator Estes Kefauver’s investigations in the early 1950s, and were fleshed out a decade later by the McClellan Senate Committee and the work of U.S. Attorney General Robert F. Kennedy. Yet the familiar, often weirdly romanticized tales of internecine warfare among crime families with names such as Genovese and Gambino are mostly the products of the criminal culture of the 1960s and 1970s. Though “the Mafia” as depicted by filmmakers such as Martin Scorsese was real enough, it wielded just a fraction of the power of its predecessors, which went by names like “the syndicate” or “the rackets”—and which stood with one leg in the criminal underworld and the other in the “legitimate” worlds of business and politics. It was this systemic culture of corruption that McDonald revealed, and that posed a threat large enough to be seen from the White House.
I’ve long been interested in O’Dwyer’s story. I have a beloved uncle whose father was a big shot in the syndicate run by the gangster Abner “Longie” Zwillman. My curiosity about my uncle led me to accompany him on his travels, and I have spoken at length with men who wound up living in mansions in places like West Palm Beach after making fortunes in the world of American organized crime. As a teenager interested in local New York City politics, I was also lucky to meet Paul O’Dwyer, William O’Dwyer’s brother and closest political adviser, and was charmed by his Irish brogue and passionate advocacy for social justice.