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Don Johnson, Michael Wilson and Andy Pringle at the Walrus Foundation Garden party.Tom Sandler

When Rob Ford's office was compiling a list of preferred candidates to fill vacant board positions two years ago, it was Councillor Doug Ford who persuaded staff to give the highest profile spot of all – an empty place on the Toronto Police Services Board – to long-time provincial Tory fundraiser Andy Pringle.

In an about-face on Tuesday, Mr. Ford launched a very public attack against Mr. Pringle and his relationship with Toronto Police Chief Bill Blair.

The calculated strike marks a new low in relations between the mayor and the chief and, according to PC insiders, the start of a proxy war against John Tory, the man many believe will be Rob Ford's chief political challenger on the right in the 2014 election, with the key support of Mr. Pringle.

During a blitz of morning radio shows and a city hall news conference, Doug Ford called for Mr. Pringle's removal from the police board for being too cozy with the chief. "I do not have confidence in Andy Pringle," he said. "He went on a fishing trip with the chief."

Neither Mr. Pringle nor Chief Blair dispute the facts of the allegation. Two years ago, shortly after assuming his new role on the board, Mr. Pringle, an avid fisherman, invited the chief on a three-day trip to a fishing camp on the Keswick River in New Brunswick where Mr. Pringle is a member.

"I considered it part of my responsibility to find out about the organization I'm a board member of, to get to know the issues and challenges better," said Mr. Pringle, when reached on Tuesday morning. "I don't see that as unusual."

He said he told board chair Alok Mukherjee of the trip and mentioned it to fellow board members, but didn't see any problem considering Dr. Mukherjee had taken the chief to India a year earlier. "The chair certainly knew of the trip. He had done the same thing himself," Mr. Pringle said. "I didn't see I needed permission."

The two drove to New Brunswick in the chief's car, according to police spokesman Mark Pugash. Chief Blair paid for gas; Mr. Pringle covered the accommodation. The chief landed two large salmon.

Board vice-chair Councillor Michael Thompson said that while the trip doesn't appear to violate any specific board rules, "there's the optics and people will question it."

"Oftentimes, I'm invited to do things with folks and I've said, 'No, because I'm providing oversight,'" Mr. Thompson added. "I've been invited to people's homes for dinner and I've chosen not to go, because I don't want what has happened today to Mr. Pringle to happen to me."

In spurning such a stalwart of the Progressive Conservative establishment, Mr. Ford is not turning against the party he's mused openly about representing, but rather a faction within it that poses a potential threat to Mr. Ford's lock on conservative voters, according to party insiders.

Mr. Tory is widely expected to enter the 2014 mayoral race and he'll count on the support and fundraising ability of Mr. Pringle, who worked as Mr. Tory's chief of staff when the latter was leader of the opposition.

"This is clearly a shot at [John] Tory, at that whole wing of the party," said one PC insider, who requested anonymity.

The relationship between Mr. Pringle and the Fords wasn't always so strained. When Mr. Pringle ran as the Tory candidate in the 2007 provincial election in the riding of Etobicoke Centre, Rob and Doug Ford, along with their mother, campaigned door-to-door with him.

"The entire family supported him strenuously," said a close friend of Mr. Pringle's. Mr. Pringle lost to Liberal Donna Cansfield, who has held the seat since 2003.

Since retiring as a managing director at RBC Capital Markets, Mr. Pringle, who wears suspenders as a sort of signature accoutrement, has been a fixture on the boards of a wide-range of charitable organizations and has allies from across the spectrum.

He is best known for his nearly two decades of work at CANFAR, the Canadian Foundations for AIDS Research, but has also served on the boards of the 519 Community Centre, the outreach centre in the heart of Toronto's gay village, and Upper Canada College. He served as chairman of the UCC's board in 2007 when the prestigious private school settled with, and apologized to, former students who had been sexually abused by a handful of teachers.

With reports from Kathryn Blaze Carlson and Greg McCarthur