When the 18th Amendment was ratified by the United States government in January of 1919, the era of prohibition was on the way. One year later, the terms of the amendment were enacted, and the country went dry on Jan. 17, 1920. In addition to the lifestyle changes the 18th Amendment brought, another major impact was seen and felt across the nation: bootlegging.
The banishment of the manufacturing and sale of alcohol products led to a prime opportunity for illegal profit. Via organized crime, bootleggers notably smuggled millions of dollars worth of prohibited products across the border and into the country. Earning sizeable profits, many of the orchestrators quickly became famed mobsters.
Among these famous criminals, one from the Hell’s Kitchen neighborhood of New York City sticks out. Bill Dwyer, considered one of the top bootleggers during prohibition, made a fortune from the practice. Smuggling products from Europe into Manhattan, he eventually earned political protection over his operation.
Despite the success of his bootlegging business, conspiracy charges led to Dwyer’s arrest in 1925. Following his arrest, Dwyer began to pivot to another stream of revenue. More specifically, the “king of bootleggers” found his way into the realm of professional sports.
Entry into the NHL and NFL
Dwyer’s first entry into the sports world came just before his arrest. The National Hockey League’s Hamilton Tigers made the headlines in March of 1925, but not for their success. Despite finishing the season with the most points, the Tigers did not play in the playoffs. This was due to an ongoing players’ strike, as the Tigers’ players were shorted $200 of their contracted pay.
Instead of requiring the Tigers to correctly pay their players, the NHL instead forced the sale of the team’s contracts. Here, Dwyer stood up and purchased the rights to Hamilton’s players. With his newly acquired team, Dwyer introduced the league to the New York Americans for the 1925-26 season.
The Americans, often referred to as the “Amerks,” played in Madison Square Garden. Dwyer personally invested in the installing of equipment in order to host an ice rink within the arena. Despite Dwyer’s efforts to bring the franchise to New York, his arrest caused him to miss their inaugural game.
Being the newest addition to the NHL, the Amerks also became New York’s first team, coming a year before the famed Rangers. The Amerk’s players noted the heavy party culture surrounding the team, emphasized by the team’s motto, “Join the Americans and laugh yourself to death.”
The Americans weren’t Dwyer’s sole venture into NHL ownership. Using the boxer Benny Leonard as a front, Dwyer secretly purchased the Pittsburgh Pirates — yes, named after the National League baseball team. With the purchase occurring during the start of the Great Depression, it is no surprise that the Pirates faced great financial struggles.
Furthermore, despite the franchise’s new ownership group, said struggles continued in the following year. In addition to their finances, the team fell short of expectations on the ice, too. In the 1929-30 season, the Pirates placed last in their division with an abysmal record of 5-36. Considering these factors, the Pirates moved to Philadelphia for their next season and the franchise folded the following year.
Dwyer’s presence in the world of professional sports did not stop at ice hockey. In the same year of the Pirates’ purchase, Dwyer also bought the Dayton Triangles. The Triangles were one of the founding members of the National Football League. After their purchase, the team moved to the Empire State. Playing in Brooklyn’s Ebbets Field, the team took on the former name of the city’s baseball team: the Brooklyn Dodgers.
The Dodgers’ best season came in their first year of 1930, where they finished fourth in the league. Despite their promising start, the Brooklyn franchise would soon become unfamiliar with success. Over the three years of Dwyer’s ownership, the Dodgers earned a collective record of 12-25.
With Dwyer losing an estimated $30,000 in his ownership of the Dodgers, he quickly lost interest in the role. As a result, he sold the team to Chris Cagle and John “Shipwreck” Kelly, who formerly played for the New York Giants.
Throughout the ’30s, the federal government engaged in trials against Dwyer. As time continued and with the end of the prohibition, Dwyer lost major portions of his wealth. In 1939, he owed $3,715,907 in taxes and penalties to the federal government. Due to his lack of funds, the NHL seized the New York Americans, his last remnant of professional sports ownership, in 1937.
