James F. Callahan was the owner of the Pittsburgh Yellow Jackets and later the Pittsburgh Pirates of the National Hockey League. James, who had the reputation as a frugal businessman, was a lawyer from Pittsburgh's Lawrenceville neighborhood.
In 1925, the Yellow Jackets were owned by former referee Roy Schooley. After winning the US Amateur Championship in 1924 and 1925, the Yellow Jackets are sold to Callahan who wanted to get the team into a professional league. Schooley sold the team to Callahan due to financial hardships. Callahan changed the team's name to the Pittsburgh Pirates, borrowing the nickname from Pittsburgh's professional baseball team. Callahan was able to use the Pirates nickanme after he cashed in favor from Pirates owner, Barney Dreyfuss. The Pirates would become the NHL's third U.S.-based team on November 7, 1925 in joining the New York Americans and the Boston Bruins. Callahan's brother, who was a member of the [Pittsburgh Police Department, offered used emblems from police jackets to place on the uniform sleeves.
On October 8, 1928 financial problems forced Callahan to sell the team to an ownership group which included Bill Dwyer. However, because he already owned the New York Americans, Dwyer had ex-lightweight boxing champion, Benny Leonard act as the team's owner.