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File photo of David Holland, president and CEO of Torstar.Aaron Vincent Elkaim/The Canadian Press

The president and chief executive officer of Torstar Corp., David Holland, will retire later this year, paving the way for a new regime to take charge of the company that publishes the Toronto Star at a difficult stage in its history.

Torstar announced Wednesday that Mr. Holland, 58, who joined the company in 1986 and has served as CEO for seven years, will leave this fall. A search for his successor is under way.

Mr. Holland has had a long and trusting relationship with Torstar chair John Honderich, steering business matters for the company. But his decision to retire comes only two months after John Cruickshank stepped down as the Star's publisher, with Mr. Holland assuming his duties. The back-to-back departures offer a chance for Torstar to reshape its senior ranks as it grapples with upheaval in its finances and its culture.

When he left, Mr. Cruickshank suggested it was time for generational change as newspapers navigate a difficult shift to digital platforms. Mr. Holland's successor will fill a position bridging business and editorial as president and CEO of Torstar as well as president of the Star Media Group papers and publisher of the Star. The dual role removes the potential for clashes between the CEO and publisher, but requires a versatile executive with the skills to steer a daunting turnaround.

Some industry veterans see Lorenzo DeMarchi, Torstar's chief financial officer, as one of the leading internal candidates, but Torstar will also look outside its ranks with help from the executive search firm Caldwell Partners.

In an internal note to staff, Mr. Holland said he will help with the transition to a new CEO, and that he is leaving "with mixed emotions" to spend more time with family, to travel and to work on other commitments.

"From a personal perspective, this is the right time for me to retire," he wrote. "These are not the easiest times in our industry but seeking opportunity and confronting the challenges we are facing alongside so many of you has been a great privilege."

Neither Mr. Holland nor Mr. Honderich responded to requests for interviews. But Torstar spokesman Bob Hepburn said, "The board was not looking for a change in leadership. This was David's decision."

The first half of 2016 has been hard on Torstar. It has struggled financially, posting a $53.5-million loss in the first quarter due mostly to one-time charges including restructuring costs from the closure of the Star's printing plant in Vaughan, Ont. Print advertising revenue at Torstar's papers is expected to continue declining through the back half of this year, in line with industry-wide trends, and readers have been slower than the company expected to adopt the Toronto Star's ambitious tablet edition as a regular habit.

Investor confidence in the company is waning and Torstar's stock price has plunged as a result. Shares fell 3.6 per cent to $1.59 on the Toronto Stock Exchange on Wednesday, down from $5.95 a year ago.

Mr. Holland's most noteworthy decision as CEO may have been the 2014 sale of romance novel publisher Harlequin Enterprises Ltd. to Rupert Murdoch's News Corp. for $455-million. The deal allowed Torstar to wipe out its debt, but also eventually funded its $180-million purchase of a 56-per-cent stake in VerticalScope Inc. last year – a digital publisher with more than 600 forum-style websites catering to enthusiasts.

"The media industry everywhere has been undergoing the most turbulent times ever, and David's steady hand on the Torstar tiller is much appreciated," Mr. Honderich said in his own memo to staff on Wednesday. "We respect his decision to retire and wish him the very best."

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