The newspaper was first published as The Leader in 1883 by Nicholas Flood Davin, soon after Edgar Dewdney, Lieutenant-Governor of the North-West Territories, decided to name the vacant and featureless site of Pile-O-Bones, renamed Regina by Princess Louise, Duchess of Argyll, the wife of the Governor General of Canada, as territorial capital, rather than the previously-established Battleford, Troy and Fort Qu'Appelle, presumably because he had acquired ample land on the site for resale.

"[2] Published weekly by the mercurial Davin, it almost immediately achieved national prominence during the North-West Rebellion and the subsequent trial of Louis Riel.

Maclean obtained this by masquerading as a francophone Catholic cleric and interviewing Riel in French under the nose of uncomprehending anglophone watch-house guards.

Also around this time, it was acquired by the Sifton family It then moved to a multi-story building across Hamilton Street to the south of the Simpson's department store.

In 1920, the Leader merged with another paper, the Regina Evening Post, itself in a building on Twelfth Avenue at Rose Street before the merger, and continued to publish daily editions of both before consolidating them under the title The Leader-Post in 1930.

Decline of local news coverage radically occurred in 1996, when the paper and its sister, the Saskatoon StarPhoenix, were acquired from their owner based in Markham, Ontario, Armadale group, by Hollinger Inc., a company that was headed by the Canadian media baron Conrad Black.