shot. Gilroy had previously been aligned as a conservative, but felt that as an independent candidate he could appeal to both liberal and conservative voters. Sexsmith won the by-election by 238 votes over Gilroy. On June 25, Gilroy was nominated as the Liberal-Progressive Party candidate in the Portage la Prairie electoral district for the July 1936 Manitoba general election. The election was a rematch versus the incumbent Toby Sexsmith. Gilroy had since completed his terms as president of the CAHA, and the Medicine Hat News described the election as a "Battle of the Sports Moguls", compared to the Winnipeg Free Press which called it a "Battle of Hockey Moguls". Gilroy received 1279 votes and was defeated again by Sexsmith who received 1727 votes. Later hockey career Gilroy was named to the MAHA executive in the past-president role, in October 1936. He was among the dignitaries which attended the opening of the new concrete and steel hockey rink in Portage la Prairie in January 1937. Portage la Prairie was the only Canadian city at the time to have two former CAHA presidents as residents, in Gilroy and Sexsmith, who both participated in the ceremonial first puck at the new rink. As the past-president of the CAHA in May 1937, Gilroy was given the honour of presenting the Memorial Cup trophy to the Winnipeg Monarchs for a second time. The first was for the 1935 Memorial Cup championship and then again for the 1937 Memorial Cup championship. Gilroy was appointed chairman of the rules committee to examine changes at the CAHA general meeting in April 1938. He submitted a motion to ban commercial teams from competing for the Memorial Cup or Allan Cup, but it was defeated without debate. He also recommended to allow strengthening of teams from within their own branch, once the team won its branch championship and advanced into the national playoffs. Gilroy was named manager of the Portage Terriers junior hockey team in May 1938. He felt that he had assembled the best Portage team of the 1930s, in preparation for the 1938–39 season. He later became team president and a director of the Portage Rink Company. Gilroy was a guest of the MAHA silver jubilee held in Winnipeg in October 1938, with five of the six past-presidents in attendance. The CAHA held its own silver jubilee in April 1939, at the Royal Alexandra Hotel in Winnipeg. Gilroy