How long can Sun-Times survive without guardian angel Jim Tyree?

The future of the Chicago Sun-Times was suddenly cast in doubt Wednesday with the death of Jim Tyree (pictured above), the man who rescued the newspaper at the 11th hour and led its parent company out of bankruptcy.

Tyree, 53, a lifelong Chicagoan and prominent business leader who was chairman and CEO of Chicago-based Mesirow Financial since 1994, died of complications from stomach cancer. He had been battling numerous health problems for years.

As the Sun-Times moved perilously close to liquidation in 2009, it was Tyree who formed a local investment group that took over the company and achieved union concessions that kept the city’s No. 2 newspaper in business. It's been a struggle ever since.

In a statement to employees Wednesday, Jeremy Halbreich, Sun-Times Media CEO, said:

Jim was an important voice of our investor group, and they will shortly select his replacement as our chairman.  Our entire management team remains intact and committed to the long-term success of Sun-Times Media, and each of our publications and web sites. We will miss Jim’s counsel and leadership. With his memory foremost in our minds, we will push on to achieve the great things that he saw in store for us.

But without Tyree at the helm and with Sun-Times Media still losing money, questions linger about how long the remaining investors may be willing to continue to sustain losses. Wave after wave of cutbacks have shrunk the newspaper’s staff and reduced the company’s suburban operations as well.

Tyree was a strong advocate of converting his print operations into digital news. Within the next decade, he told Bloomberg News last year, “You’ll have to evolve into something else — maybe five years evolve into something else — or you’ll just be out of business.”

A glimpse into the company's survival strategy may be in the push to convert subscribers to the new Chicago Sun-Times E-paper, a digital replica of the print product delivered via e-mail by 7am each day. Subscribers to the company’s Pioneer Press suburban papers are being offered one-year subscriptions to the Sun-Times E-paper for as little as $1.