He started off as a simple dockworker, segued into bootlegging on a large scale, and was known and the “King of the Rum Runners.” Big Bill Dwyer made so much money, he was partners with known gangsters in several swanky New York City nightclubs. Dwyer also owned two professional hockey teams, including the New York Americans, and was owner of the Brooklyn Dodgers football team. However, in the end, when Big Bill Dwyer passed away, he died out of the limelight, and flat broke.

William Vincent Dwyer was born in 1883 in the Hells Kitchen area on the west side of New York City. Two gangs, the Hudson Dusters and the Gophers, ruled Hell’s Kitchen at the time, but Dwyer avoided joining both gangs, and instead took a job on the docks as a stevedore for the International Longshoremen’s Union (ILU).

While working on the docks, Dwyer started his own bookmaking operation. After the Volstead Act was enacted in 1919, banning the distribution of alcohol, with the money he made from bookmaking, Dwyer branched out into the bootlegging business. Dwyer purchased a fleet of steel-plated speedboats, each with a mounted machine gun, in case crooks tried to hijack a shipment. Dwyer also purchased several large rum-running ships, which were needed to offload the illegal hootch from whatever boat was supplying it.

Dwyer traveled to Canada, England, and the Caribbean to establish ties with those who sold him the liquor he needed to smuggle into the United States. Then Dwyer set up a system whereby his ships would meet the ships, that were supplying him the liquor, many miles out at sea. There the booze was transferred to Dwyer’s ships, then quickly transported to Dwyer’s speedboats, which were closer to the shore of New York City.

The speedboats were unloaded at the docks, which were protected by Local 791 of the ILU, of which Dwyer was a charter member. From the docks, the liquor was moved to several warehouses in the New York area. When the time was right, trucks filed with illegal alcohol, and protected by convoys of teamster members, transported the booze all over the country: with heavy shipments going to Florida, St. Louis, Kansas City, Cincinnati, and as far away as New Orleans.

Dwyer was able to smuggle large amounts of booze into New York City because he knew one simple fact: you had to bribe the police and the Coast Guard if you wanted to be successful in the bootlegging business. And that Dwyer did, handing over thousands of dollars to whomever needed to be greased.

Paying off New York City cops was easy. The cops who didn’t have their hands out for graft money were far and few between. However, Dwyer was especially skillful in recruiting Coast Guard members to look the other way, when his speedboats were entering New York waters.

Dwyer’s first contact was Coast Guard Petty Officer Olsen. Through Olsen, Dwyer met scores of Coast Guardsmen, “Guardies” he called them, who might be willing to take bribes. Dwyer would bring these Guardies into the bright lights of New York City, where he would feed them sumptuous meals, take them to Broadway shows, and even get them a swanky hotel room, occupied by the lady of their choice, whom Dwyer would pay for too. Once a Guardie took a bribe from Dwyer, he was informed that he could earn hundreds, and sometimes thousands of dollars more, if he could enlist other Guardies to help protect Dwyer’s shipments.

Soon, Dwyer was making so much money through bootlegging, he was considered the largest distributor of illegal alcohol in the entire United States of America. However, Dwyer had one huge problem, which he needed help in solving. Whenever one of his trucks left New York to distribute the booze to other parts of the country, they were vulnerable to being seized by the hundreds of hijackers who operated throughout the country. Dwyer knew to stop this from happening he had to take in partners – members of the Italian mobs, and the Jewish mobs. Since he was raking in millions in profits, Dwyer didn’t mind, and certainly could afford to share the wealth. The problem was, Dwyer considered himself no more than a businessman, and wasn’t a gangster himself. Dwyer needed someone in the underworld who could make the contacts Dwyer needed to continue to operate without fear of being hijacked.

Almost by accident, that person fell right into Dwyer’s lap. In 1924, two of Dwyer’s shipments were hijacked in upstate New York. Dwyer leaned on the cops on his payroll to find out who was responsible for the hijackings. Word soon came back to Dwyer that the perpetrator, who was arrested for the hijackings, was none other than Owney Madden, an Irishman himself, who grew up in Liverpool, England, before he emigrated to New York as a teenager. Madden was a vicious con nicknamed “The Killer” and had once ruled the murderous Gopher’s gang in Hell’s Kitchen.

Dwyer paid whomever needed to be paid to get the charges dropped against Madden, with the order, “Get me Owney Madden. I want to talk to him. I’ve got a business proposition we need to discuss.”

Madden got the word who his benefactor had been, and that a meeting with Dwyer was expected of him in return. The two men met at Dwyer’s office in the Loew’s State Building in Times Square. There is no recording, or transcript of this meeting, but T.J. English, in his masterpiece on Irish gangsters called Paddy Whacked, said the conversation between Madden and Dwyer might have gone something like this:

“You’ve got a problem,” Madden would have told Dwyer. “Gangsters have been picking off your trucks like sitting ducks and what are you going to do about it?”

“That’s why I called you here.”

“You gotta organize the shooters and the cherry-pickers, not to mention the bulls (cops) and the pols (politicians).”

“You’re right. I need the hijackings to stop. I need a place to make my own brew right here in the city. Protected by the Tiger and the coppers. And I need outlets – speakeasies, nightclubs, you name it.”

“You need a lot, my friend.

“Are you with me?”

“Give me one reason why.”

“I can make you rich.”

“Pal, you and me are two peas in a pod.”

And that was the start of the New York City Irish Mob, which would then unite with the Italian and Jewish mobs to control the bootlegging business throughout the United States of America. The grouping of the three ethnic mobs was known as the “Combine.”

With Dwyer’s millions, Madden oversaw the creation of the Phoenix Cereal Beverage Company, which was located on 26th Street and 10th Avenue, right in the heart of Hell’s Kitchen, where both Madden and Dwyer had grown up. This red-brick building, which comprised the entire block, was originally the Clausen & Flanagan Brewery, which was created to produce and sell near-beer, which no true beer-drinker would ever let pass their lips. The beer produced at the Phoenix was called Madden’s No 1.

With Dwyer basically the money man behind the scenes, Madden became the architect who created and nurtured their empire. Madden brought in a former taxi business owner named Larry Fay as the front man for several high class establishments, that were needed to sell Madden No. 1, plus all the scotch, rum, vodka, Cognac and champagne that the Combine was smuggling into the city. One of these places was the El Fay at 107 West 54th Street.

The main attraction at the El Fay was Texas Guinan, a bawdy cabaret singer/comedienne, who was later copied by May West. To entice Guinan to work at the El Fay, Madden and Dwyer made Guinan a partner. Guinan was famous for her wisecracks, which she belted out between clacks from a clacker, or toots from a piercing whistle, while she was sitting on a tall stool in the main room. Guinan’s signature saying was “Hello Sucker,” which is how she greeted all the well-healed El Fay customers.

When a singer or a dancer finished their performance at the El Fey, Guinan would exhort the crowd to “Give the little lady a great big hand!”

One day, a prohibition agent, who couldn’t be bought by Madden or Dwyer, raided the El Fey. He marched over to Guinan, put his hand on her shoulder and said to his fellow agent, “Give the little lady a great big handcuff.”

Dwyer did what he did best, Guinan was released from prison, and the El Fey was soon hopping again, making everyone involved very rich indeed.

Madden and Dwyer also partnered with former bootlegger Sherman Billingsley at the very fashionable Stork Club on East 53rd Street. The two Irish gangsters spread their wings to the north part of Manhattan when they bought the Club De Luxe from former Heavyweight Boxing Champion Jack Johnson. They inserted Big Frenchy De Mange as their operating partner, and changed the name to the Cotton Club. At the Cotton Club, De Mange instituted a “Whites Only” admittance policy, despite the fact the waiters, dancers, and headline entertainers, like Cab Calloway, Duke Ellington, Louis Armstrong, Lena Horne, Bill “Bojangles” Robinson, and the Nicholas Brothers, were all black.

Still, the Cotton Club was wildly successful with the big spenders from downtown, putting tons of cash into Dwyer and Madden’s pockets.

In 1925, Dwyer was arrested for attempting to bribe Coast Guard members during a sting operation headed by the Prohibition Bureau. Dwyer was sentenced to two years in prison, but he was released after 13 months for good behavior. With Dwyer in the can, Frank Costello took over Dwyer’s bootlegging business.

While he was in prison, a despondent Dwyer said to one of his cell mates. “I wish I had never seen a case of whiskey. I spent years in daily fear of my life, always expecting to be arrested, always dealing with crooks and double-crossers, and now look at me. My wife is heartbroken and I am worse than broke.”

As we shall see, that was not exactly the truth.

When Dwyer hit the streets again, he eased out of the bootlegging business, leaving the rum-running operation to Costello and Madden. To pass his time, Dwyer started investing in legitimate business, especially sports teams.

In 1926, boxing promoter Tex Rickard conned Dwyer into buying the Hamilton Tigers of the National Hockey League. Dwyer did so, and he moved his team into New York’s Madison Square Garden, and re-named them the New York Americans. As smart as Dwyer was in running the bootlegging business, he was just as dumb in running a hockey team. His pockets bursting with bootlegging cash, Dwyer’s strategy for winning was basically to over-pay everybody on his team. With the average hockey player making between $1500-$2000 a year, Dwyer gave Billy Burch a 3-year $25,000 contract. Shorty Green also got a huge raise, when Dwyer awarded him a $5000 a year contract.

Being an old crook at heart, Dwyer took an active part in running his team, even going so far as to try and rig the games. Dwyer paid off goal judges to rule his team had scored a goal if the puck just touched the goal line, instead of completely passing the goal line, which was the rule.

At a game in 1927 in Madison Square Garden, the goal judge, whom Dwyer had in his pocket, for some unknown reason started taunting Ottawa goalie Alex Connell. Connell responded by butt-ending his hockey stick into the goal judge’s nose. Dwyer became incensed at the Ottawa goalie’s actions (You don’t manhandle one of Dwyer’s employees), and Connell was told to leave town quickly after the game. A police detail took Connell to the train station, and protected him until the train was safely out of town. After the train left the station, a man asked Connell if he was the Ottawa goalie Alex Connell. Connell afraid for his life, told the stranger no. And, as a result, he lived to goalie other hockey games.

Bypassing a league rule that a person can’t own two hockey teams, in 1929, Dwyer, using ex-lightweight boxing champ Benny Leonard as his front man, purchased the NHL’s Pittsburgh Pirates. In 1930, Dwyer inserted his grubby fingers into the newly-formed National Football League too, by buying the Dayton Triangles for $2,500. Dwyer moved the team to Ebbets Field in Brooklyn, and renamed them the Brooklyn Dodgers.

In three years, Dwyer, again overpaying all his players, began losing so much money, he sold the Brooklyn Dodgers to two former New York Giant Football players: Chris Cagle and John Simms, for $25,000. Even though he sold the team for 10 times more than he had paid, Dwyer estimated he still lost $30,000 in the three years he owned the team.

In 1934, having his fill of America sports teams (he still owned the New York Americans, but they were bleeding money), Dwyer bought the famed Tropical Park Horse Racing Track in Miami, Florida.

However, the roof fell in on Dwyer, when in 1935, he was indicted on a gambling charge. Dwyer beat that case, but then the government did to him what they did to Al Capone: they hit him with tax evasion charges. Those charges stuck, and Dwyer was stripped of all his assets, except the New York Americans, and a house in Belle Harbor, Queens. Almost penniless, Dwyer no longer had the money to keep the New York Americans afloat.

In 1937, the National Hockey League temporarily took control of the New York Americans. To show the NHL that he was financially solvent, Dwyer borrowed $20,000 from Red Dutton. However, instead of paying his team’s salaries, Dwyer decided to try to multiply his money in a craps game. That didn’t go over too well, when Dwyer busted out, and lost the entire twenty grand. Unable to pay his team, and unable to raise any more capital, the NHL booted Dwyer out permanently, and took final control of the New York Americans. Broke and despondent, Dwyer retired to his Belle Harbor home.

On December 10, 1943, Big Bill Dwyer, the “King of the Rum Runners” died at the age of 63. Dwyer was reportedly penniless at the time of his death, his only asset being the roof over his head.

Source by Joseph Bruno