Born February 23, 1883.
Bill Dwyer was raised in the rough and tumble of Hell’s Kitchen, though he largely succeeded at avoiding the temptations of young gangsterism, a colorful but hard-working young man. He remained loyal, however, to his fellows, and was known as a dependable guy even as he eschewed the criminal life. He finished public school and worked for a time as an usher before finding more steady, if dangerous, employment as a stevedore on the Chelsea Piers. Approaching a kind of financial stability, Dwyer married a girl from his home block, Agnes Frances Cassidy, moving into a small four room flat and beginning a family together. He maintained steady, sober employment, content with what he had.
Dwyer was 37 and set in his ways when Prohibition became law in 1920. A close friend from his childhood, George J. Shevlin, found himself cut from material support with the enactment of the new law, having been the owner of a string of shabby saloons near the Chelsea Piers. However, as he struggled to keep clientele through bootleg alcohol, it soon became clear that a much more lucrative opportunity lay nearby, in the form of dozens of warehouses owned by the government, packed with confiscated illegal alcohol. A lively market in this alcohol, liberated from storage via false permits, bribery, robbery, or burglary, began the moment Prohibition came into effect. Shevlin, working with a small group of longshoremen, former gangsters all, entered into this business, preying upon the warehouses. Shevlin approached Dwyer, asking him if he wanted to be partners in this new venture. Dwyer went for it.
Shevlin and Dwyer largely pursued a policy of nonviolence in their attempts to get at the liquor stored by the government, offering bribes and false permits to withdraw industrial alcohol, which was then sold to other bootleggers to make liquor. As the business grew they invested carefully, accruing warehouses, trucks, and men to guard the lot, violence increasing as the profits did. A key development in Dwyer’s reputation and later success came early and accidentally to the eventual King of the Bootleggers. In May of 1921, Shevlin, found it expedient to leave town, handing Dwyer $2,500 to use in an emergency. That emergency arrived quickly and from an unexpected source - despite Dwyer’s already close relationship with New York police, he found himself pulled over by a couple detectives while riding on a liquor truck. They insisted on a payment and, unwillingly, Dwyer passed on Shevlin’s emergency funds. Worried about Shevlin’s reaction, once the liquor was safely delivered, Dwyer returned to police headquarters, attempting to recover the funds. He met with a wall of indifference and produced another unforeseen result, jump-starting the departmental rumor mill concerning the detectives and the princely sum given to them by Dwyer. The net result was that when the rumors had coalesced into an investigation into the detectives some months later, Dwyer had seen the sudden use of the money. Called to testify, he remained silent, considering his unwilling investment now a wise one and guaranteeing to any police now interested in doing business with him his protection. The money and the silence - by these means Dwyer laid the foundation for what would eventually become a bribery network spanning the police departments of the entirety of Long Island and reaching into federal agencies such as the Prohibition Department and, particularly, the Coast Guard.
His reputation secured and his stature enhanced in the syndicate he’d created with Shevlin, Dwyer only continued to develop, quickly assuming more and more control over the enterprise and becoming recognized as its head. Especially as the going continued to get rough, Shevlin dropped out, leaving Dwyer in sole control of what was quickly becoming a multi-million dollar operation. However, Dwyer soon found himself running against the many other liquor smuggling concerns in the city, struggling with them for territory, product, and profit.
Dwyer infiltrated deep into American government, placing men in law enforcement, the police, and the coast guard on his payroll, not to mention solidifying Tammany and gangster connections to insulate himself and his organization against any kind of legal action. Finally, in 1923, famous gangster Owney “the Killer” Madden was released from a ten year stretch in the federal penitentiary. Known for the violent temperament of his younger days, prison had hardened Madden into a mature man capable of violence but also possessed of a cool head and a calm demeanor. Dwyer paid the best price for his services, making Madden a full partner in his organization. Beyond muscle services, Madden also established the Phoenix Cereal Beverage Co., a brewery in the heart of the West Side, filling the area with the scent of illegally produced beer, Madden’s No. 1. Protected in Dwyer’s web of political connections, they remained untouched and made more money than even they had thought possible, coming to dominate the alcohol trade in New York.
But their success came with a consequence, drawing the attention of the authorities. In 1924, the Coast Guard, along with the negotiation of a treaty to extend the maritime borders of the United States some score miles, stepped up their efforts against bootlegging along the American coast, virtually eliminating Rum Row and forcing those who’d profited so greatly from it, especially Dwyer, to invest in literal fleets of their own ships to handle the difficult business of overseas and ship to shore transportation. Also faced with the construction of new, faster Coast Guard ships specially equipped to halt the alcohol trade, Dwyer turned to a friend, who, purchasing at bottom prices hundreds of airplane engines left over from the Great War, outfitted them on Dwyer’s cutters, thus creating a fleet of ships faster than any on the world’s seas.
Meanwhile, Dwyer also began to branch out into legitimate business ventures, purchasing a great deal of property, restaurants, businesses, unconnected with his bootlegging empire. Most particularly, he purchased a struggling Canadian hockey team, the Hamilton Tigers, relocating them to New York and rechristening them the Americans.