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. 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.
Shorty Green also received a huge raise, his salary going from $3,000 to $5,000. This was a time when most NHL players were said to make about $1,500 or $2,000. He took an active role in owning the team, often trying to rig NHL games. For example, he put in a goal judge who would call a goal against an opponent if the puck merely touched the goal line. It happened one night in 1927-28 when Ottawa was at Madison Square Garden. However, the goal judge seemed more interested in taunting Ottawa goalkeeper
Alex Connell. Connell finally butt-ended the goal judge in the nose, which caused Dwyer's buddies to seek Connell's death that night. It took a police detail to get Connell out of the Gardens that night and at the train station, someone inquired if a gentleman was Alex Connell. Connell, knowing he was in danger, lied and said he was not. 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. The team folded in 1930 as the
Philadelphia Quakers. In 1930, Dwyer also purchased the NFL's
Dayton Triangles for $2,500, relocated them to
Ebbets Field and renamed them the Brooklyn Dodgers. He bought the team with
Jack Depler, a former player for the NFL's
Orange Tornadoes. By the end of the 1932 season, Dwyer had enough of professional football. The Dodgers, had cost him an estimated $30,000 in just three years. The team was then purchased by two former
New York Giants players,
Chris Cagle and
John Simms Kelly for $25,000. 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. Just before the 1936-37 season, the NHL took control of the Americans, claiming that the financial status of the team was critical. Dwyer filed a lawsuit against the NHL challenging this action, then setting with the NHL, which let him retain the Americans in 1936-37 to give him time to pay his debts.
Red Dutton, who was manager and coach of the team, lent Bill $20,000 for the team and Dwyer promptly lost it all in a
craps game. When, at the end of the season, he could not pay the debts he owed, the NHL ordered the team under its control. ==Thoroughbred racetrack ownership==