Thomas Gilroy was a Canadian politician, the 14th Mayor of Winnipeg in 1895.

Gilroy was born in Norfolk County

Norfolk County, Ontario

Norfolk County is a rural city-status single-tier municipality on the north shore of Lake Erie in Southwestern Ontario, Canada. Bloomsburg is a small town located in Norfolk County and is the hometown of David Slater. The county seat and largest community is Simcoe...

, Canada West. In 1872 he joined the Sun Life Assurance

Sun Life Financial

Sun Life Financial Inc. is an international financial services company known primarily as a life insurance company. Based in Toronto, Canada, Sun Life and its partners provide insurance, retirement and investment solutions for individuals and businesses around the world including Canada, the United...

 company, supervising its Ontario operations. He moved west in 1882 to be Sun Life's manager for the North-West region, including Winnipeg.

He attempted to enter provincial politics by campaigning in the 1888 Manitoba election at the Centre Winnipeg riding, but was defeated by Daniel Hunter McMillan

Daniel Hunter McMillan

Sir Daniel Hunter McMillan, KCMG was a Manitoba politician. He was a cabinet minister in Thomas Greenway's government from 1889 to 1900, and served as the seventh Lieutenant Governor of Manitoba from 1900 to 1911....

. In 1891, he became a City of Winnipeg alderman, and was elected mayor in 1894.