Founded as The Manitoba Free Press by W.F. Luxton in 1872, the newspaper displayed a distinct Liberal preference from its earliest days. It was purchase in 1898 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 Sifton appointed a young journalist from Montréal, John W. John W. Dafoe, as editor. Even after Sifton's departure from the Laurier Cabinet in 1905, the Free Press continued to support Laurier, and in 1911 it opposed its owner's personal preference by championing Laurier and reciprocity with the US.

Owner and newspaper were ideologically reunited in 1917, when the Free Press backed Union Government and Conscription. During the 1920s, however, Dafoe and Sifton returned to the Liberal fold to support 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. In 1931 the paper became the Winnipeg Free Press; 2 years earlier, when Sifton died, it had passed into the hands of his children.

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, eg, George Ferguson, Hutchison and Tom Kent, it tended to become less distinctive and more profitable.

Recent history

In 1979 the paper was purchased by the Thomson Group; it absorbed its longstanding rival, the Winnipeg Tribune, and confirmed its dominance in the Winnipeg newspaper field. The paper, along with its sister paper the Brandon Sun, 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 2015, the paper averages 106 500 readers six days a week, including over 132 500 on Saturday.