With access to company supply trucks, garages, and other valuable resources, Dwyer quickly dominated bootlegging in Manhattan within a year.
Forming a partnership with Owney Madden and, later Frank Costello, Dwyer soon began taking on future gangsters such as lieutenant Vannie Higgins[1] and others.
However, in 1925, Dwyer was arrested for attempting to bribe members of the Coast Guard during an undercover operation by the Prohibition Bureau and was sentenced for two years.
In 1925, Tex Rickard convinced Dwyer to obtain a National Hockey League expansion franchise to play in Madison Square Garden, and he named them the New York Americans, paying $75,000.
[2] With a fortune made in Prohibition bootlegging, Dwyer handed out lucrative contracts, including a three-year deal to Billy Burch rumored to be worth $25,000.
The Americans flourished, and Dwyer secretly purchased the Pittsburgh Pirates of the NHL, using ex-boxer Benny Leonard as the front man who appeared to be the team's owner.
In 1935-36, the United States government won a big lawsuit against Dwyer, leaving him virtually penniless except for his ownership of the Americans, and he was losing money here, also.
Dwyer cut a deal with Ed Strong of Cleveland for Peter Horback to purchase the race track which was in receivership on July 20, 1936 for a $5,000.00 down payment.
[6] By the end of Prohibition in 1932, Dwyer had retired from bootlegging and lived with his wife, Agnes, and five children in Belle Harbor, Queens.