[3] In 1998, he raised concerns about proposed bank mergers when testifying before a federal Liberal Party task force on financial services.
[8] Gilroy was elected to the Winnipeg City Council for the Sargent Park ward in 1986, defeating New Democratic Party candidate George Slobodzian by just under 300 votes.
Widely respected for his abilities in government, Gilroy served in Mayor Bill Norrie's cabinet during the late 1980s and early 1990s.
[11] He supported a plan to build an arena called "Manitoba Gardens" in the city's downtown, and favoured the use of private-sector money rather than requiring the team's majority owners to contribute.
[14] He criticized rival candidates Susan Thompson and David Brown for promising to introduce a tax freeze, saying that this would be impossible in the wake of reduced funding from the provincial and federal governments.
One civil servant indicated that he was a good choice to create links between elected politicians and the city bureaucracy, although some accused him of controlling the mayor's agenda.
[20] Gilroy later worked on Murray's behalf in the federal St. Boniface riding, scouting out possible supporters if the mayor chose to run as a Liberal candidate in a 2002 by-election.
Gilroy was appointed chair of the Manitoba Liberal Party's convention organizing committee in 1993, as delegates were chosen to elect a successor to outgoing leader Sharon Carstairs.
[26] He was again called to stand-in as interim chair of the provincial Liberal campaign in 1995, when original manager Allister Gunson was forced to leave the province on business.
[31] Shortly after stepping down as an aide to Glen Murray, Gilroy was appointed by the provincial government to serve as chair of the Floodway Expansion Interim Management Authority.