The company that would come to dominate the small-town Ontario newspaper market was formed in 2001 from a portion of Conrad Black's crumbling Canadian empire.

Michael Sifton, who had been installed as an executive at Hollinger Inc. after Black's company purchased his two family-owned Saskatchewan dailies, paid $220 million for 29 properties (16 daily and 13 weekly newspapers). Sifton's major backers were the Ontario Teachers Pension Plan Board and the Bank of Nova Scotia's merchant banking arm. The president and chief operating officer of Osprey Media Group Inc. reportedly owned five per cent of the new company.

Two years later, Osprey more than doubled its holdings with the purchase from CanWest Global Corporation of more than 30 newspapers, for which it paid almost $194 million.

In many small Ontario cities, Osprey's papers are monopolies. The company's stiffest competition comes from Metroland, a subsidiary of TorStar, which fiercely battles any encroachment on its greater Toronto markets.

By 2006, Osprey was describing itself as "one of Canada’s leading publishers of daily and non-daily newspapers, magazines and specialty publications." The corporate website offered the following details:

"Its publications include 21 daily newspapers and 38 non-daily newspapers together with shopping guides, magazines, telephone directories and other publications. Osprey also engages in the distribution of inserts and flyers and commercial printing for third party publications. Osprey Media’s extended market products provide flyer distribution to over 1.0 million households across Ontario.

"Osprey Media’s 21 daily newspapers offer combined average daily circulation of 309,782 while its non-dailies newspapers (both paid and unpaid) offer combined average weekly circulation of 503,813.

"Osprey Media’s local newspapers are entrenched in their communities and are well-recognized brand leaders as well as trusted local news sources. Newspapers like The Kingston Whig-Standard, The St. Catharines Standard, The Peterborough Examiner, The Sault Star and many others have been serving their communities for over a hundred years."

But after all those acquisitions, the company was deeply in debt. In 2004, Osprey went public as an income trust (Osprey Media Income Fund). While it was expected that this would lead to a greater market value for the company, it also meant there would now be pressure from unit holders to cut costs and increase profits (and cash distributions).

Citing a need for "greater efficiencies," the following year saw Sifton establish call centres in Niagara Falls and Sarnia to handle circulation and classified ads. In late 2005, Osprey began axing long-time employees at several of its daily newspapers, including its two flagships, the Kingston Whig-Standard and the St. Catharines Standard. All of the work but none of the jobs was transferred to the call centres, which Osprey was staffing with part-time employees who receive low pay and no benefits.

This flew in the face of Sifton's claim on the corporate website that the "Osprey team includes experienced senior managers, award-winning journalists, press room employees with in-depth knowledge of production and distribution, customer-driven sales professionals combined with creative production teams, business personnel, and customer service representatives. We empower our teams to act locally and to enrich the communities we serve."

TNG Canada (The Newspaper Guild), which represents employees at 10 Osprey dailies, noted that pink slips were being handed out only to unionized workers. It estimated that as many as 100 jobs could be lost at nine of those papers. And there was no way to predict how many jobs would be cut at the remaining 11 dailies and some of the larger community papers.

A TNG Canada-sponsored campaign against the outsourcing of jobs from Ontario communities was launched in February 2006. While it has won broad public support and rattled several of Osprey's publishers, it appears to have had little affect on Sifton, a fourth-generation newspaper scion who has carried on the family tradition of being unabashedly anti-union.

The great-grandson of Sir Clifford Sifton, who launched the Manitoba-Saskatchewan family newspaper empire in 1899, was profiled by Meghan Clarke in the summer 2003 issue of Ryerson Review of Journalism. The article carries the headline: Lord Sifton of Fleet? More telling is the subhead: In the last two years, Michael Sifton has purchased 60 newspapers and he's looking for more. Not good news if you're a union supporter.

Clarke writes:

As a boy, Sifton travelled to Saskatchewan with his father and used the presses at the (Regina) Leader-Post and the Star Phoenix as jungle gyms. In the newspaper business, he went from cub reporter at The Brockville Recorder and Times to reporter at the St. Catharines Standard and the Canadian Press, to co-operative advertising salesman. In 1992, he became publisher of the Star Phoenix and the Leader Post, relocating his family to Saskatoon. Bill Peterson, editor of the Star Phoenix at the time, says Sifton was "this 30-ish guy who wanted to get really involved—he just had a different approach than his dad."

Peterson remembers meeting Sifton's father, Michael Sr., in 1972 when he was working as a night copy boy at the Star Phoenix. "I'd been there a couple of months. I was working away one night, and I looked up and there's Michael Sifton Sr. coming to introduce himself. Scared the crap out of me. But he was a gentle, approachable guy." Sifton's father knew every employee by name, despite only visiting his papers a handful of times per year. But the family was most famous for its benevolent newspapering and no-layoff policy—during the Depression in the 1930s, amid wholesale-layoffs elsewhere, the Siftons never jettisoned a soul.

Today, many westerners haven't forgiven Sifton for the sale of the Leader-Post and the Star Phoenix to Conrad Black... . The papers had been the twin jewels of the Sifton empire since 1928 ...

The sale was finalized on February 29, 1996, and Black appointed Sifton chairman of the Sterling group of newspapers. Sifton's first big move as a Hollinger executive was to fire roughly 170 employees from the two papers he'd grown up with, an order he fulfilled two days into the new regime. ..."

Ten years later, Osprey Media Income Fund was coming up short on distribution requirements and analysts were predicting it would have to chop its payout to unitholders. At the annual meeting in May 2006, Michael Sifton insisted that cost-cutting would cover the shortfall and that the distribution would be maintained.

Meanwhile, rumours persisted that Sifton was trying to sell the newspaper trust, but could find no buyers. Among the speculators' list of likely buyers was FP Newspapers Income Fund, owner of the Winnipeg Free Press. The newspaper where it all began for the Sifton empire in 1899.