It took a full-court press by high-profile Tories, including an afternoon call from former premier Mike Harris, to persuade Toronto deputy mayor Doug Holyday to jump to provincial politics.
The city hall veteran announced on Thursday he will stand as the Progressive Conservative candidate for Etobicoke-Lakeshore in a by-election – a move Ontario PC Leader Tim Hudak billed as a "game-changer" for his party's efforts to break the Liberal stranglehold on Toronto.
Mr. Hudak's gain would be Rob Ford's loss.
The mayor and his brother, Councillor Doug Ford, have given their full backing to Mr. Holyday, but, if he wins, his departure will leave the mayor down another key player. In recent months, Mr. Ford's office has lost a string of staff, including a chief of staff and press secretary, amid allegations the mayor was caught on video smoking crack cocaine. Mr. Ford has denied the allegations.
Persuading Mr. Holyday to run is a coup for Mr. Hudak, and he pulled out all the stops to make it happen.
The PC leader first approached Mr. Holyday last week, shortly after Liberal Laurel Broten resigned and left the riding vacant. Mr. Hudak and Mr. Holyday spoke several times, including sitdowns at which Mr. Hudak explained his policy agenda, a Tory source said. Mr. Hudak also contacted Mr. Ford to make sure Mr. Holyday's potential move to the province was acceptable to him.
On Wednesday, during a 13-hour meeting of the mayor's executive, the calls rolled in, with Mr. Holyday stepping out frequently to answer his mobile.
It was not until the late-night drive home that he made up his mind. He rose early for a meeting on Thursday and telephoned Mr. Hudak to inform him of his decision.
At a scheduled photo-op at a Scarborough factory, Mr. Hudak broke the news to reporters.
"I'm thrilled about this," he said. "He's a guy who commands tremendous respect. He helped get the books back in balance in the City of Toronto."
During a lunch break at a committee meeting, Mr. Holyday told reporters: "I really feel strongly that we need a change at Queen's Park. If people like myself aren't willing to step up and do it, then who is going to do it? I decided to give this a try."
He fits perfectly with Mr. Hudak's strategy. While his cost-cutting, small-government credentials are beyond doubt – he quarterbacked the strategy to claw back the jobs-for-life clause in city union contracts, for instance – the 70-year-old grandfather possesses a genteel warmth, in sync with the conservatism-with-a-smile image Mr. Hudak is cultivating.
If he wins, he would also give Mr. Hudak a much-needed face for his party in Toronto, where it has not held a seat in a decade, and a toehold in the suburban ridings the Tories must win if they hope to form a government.
Mr. Holyday, a former mayor of Etobicoke, captured more than 70 per cent of the vote in his Central Etobicoke ward in the last election without spending a penny on his campaign.
He will go head-to-head with council colleague Peter Milczyn, who got the Liberal nomination earlier this week. Mr. Milczyn, also a long-serving Etobicoke politician, squeaked into office in 2010. His hard-fought campaigns have left him with an organization in the area and experience in the ground game.
Fellow Etobicoke Councillor Gloria Lindsay Luby predicted it will be a "nasty" campaign. "Anything can go. It's wide open and, of course, [Mr. Holyday] will have the Fords behind him."
Both men are members of the mayor's executive, and the mayor would have to find a replacement for either of them.
Throughout the recent months of controversy, from court hearings to election audits to allegations of drug use, Mr. Holyday has been front and centre, always willing to face the cameras and by the mayor's side for key announcements.
While Mr. Holyday and the mayor agree on most issues, they have differing views on the conduct becoming a mayor. As controversy swirled around Mr. Ford this spring, Mr. Holyday urged him to make a statement and made no secret of the fact he thought the mayor should stop skipping meetings to coach high school football.
Despite his usual avuncular persona, Mr. Holyday can also be a scrapper. This year, during council's budget debate, he tore a strip off those who wanted to add to the city's spending. Earlier, when it became clear council would not support holding the line on fire service spending, Mr. Holyday fumed that politicians had "folded like a two-dollar suitcase" under pressure from the union.
Mr. Holyday, an insurance broker by profession, lives across the street from his son and grandchildren. When council sessions drag on, he usually can be spotted following the debate from the gallery, drinking tea from his beige Thermos and eating a tuna sandwich.
As Wednesday's executive meeting stretched past the dinner hour, Mr. Holyday sat with his Thermos in front of him. The people at Queen's Park, he noted, might not keep such hours.
With a report from Sunny Dhillon