Founded as the Manitoba Free Press by William Fisher Luxton in 1872, the newspaper displayed a distinct Liberal preference from its earliest days. It was purchased in 1897–98 by Clifford Sifton, a prominent Liberal politician and Cabinet minister, and thereafter was the organ of the Liberal Party on the Prairies.
Under Editor J.W. Dafoe
In 1901, Clifford Sifton appointed a young journalist from Montreal, John Wesley Dafoe, as editor. Dafoe also hired journalist Ella Cora Hind as an agriculture editor. Previous owner William Fisher Luxton had refused to hire her as a reporter since she was a woman.
Even after Sifton's departure from Wilfrid Laurier's Cabinet in 1905, the Free Press continued to support Laurier. In 1911, it opposed its owner's personal preference by championing Laurier and reciprocity with the United States.
Owner and newspaper were ideologically reunited in 1917, when the Free Press backed the Union Government and Conscription. During the 1920s, however, Dafoe and Sifton returned to the Liberal fold to support William Lyon Mackenzie King and his government.
During this period, the Free Press was a generally profitable enterprise and ran a highly successful farm weekly. Dafoe also began to gather together a skilled group of journalists. Employing such men as A. Grant Dexter and Bruce Hutchinson, Dafoe's paper was the best informed in Canada during periods of Liberal government. The Free Press was also notable for its coverage of foreign affairs. Notably, prior to the Second World War, Dafoe argued against appeasement and isolationism.
In 1931, the paper became the Winnipeg Free Press.
Dafoe remained the dominant influence at the Free Press until his death in 1944. Although the Free Press employed some distinguished journalists as editors afterwards, e.g., George Ferguson, Hutchison and Tom Kent, it tended to become less distinctive and more profitable.
In 1980, the Thomson Group purchased the paper. The Free Press, along with its sister paper the Brandon Sun (see Brandon), was acquired from Thomson in 2001 by FP Canadian Newspapers Limited Partnership. With the purchase of the Winnipeg Free Press, FP Canadian Newspapers Limited Partnership became the owner of the largest independent newspaper in Canada.
In 2022, The Free Press claimed to have 1.15 million monthly users. The publication also reported a weekly print and digital readership of 439,000.