Councillor Paul Ainslie’s recent and very public split from Mayor Rob Ford was, in many respects, the final stop on a journey set in motion months ago, over chicken and fries in a Markham Swiss Chalet.

It was several weeks after the Garrison Ball, and Ainslie, at the time a member of the mayor’s inner circle, was grappling with a difficult decision: Should he go on the record about asking the mayor to leave?

Ainslie asked his former boss at city hall, former councillor David Soknacki, to meet him for lunch. As he told Soknacki, he had been approached repeatedly by a reporter from this paper who wanted to know whether Ainslie had told the mayor to go amid concerns about his behaviour.

“I (felt) bad for him. I considered him a friend. But he is the mayor of Toronto and he’s got to be held to a higher standard than a councillor,” Ainslie said in an interview, recalling the internal struggle he faced after the February event. “Even I went up to him, and I wouldn’t say he was perfectly sober. He was not right. He was not himself.”

After his lunch with Soknacki, Ainslie confirmed to the Star simply that he had asked the mayor to leave the dinner. He was demoted a few months later from chair of the government management committee, a move he attributes in part to going on record about the Garrison.

The mayor’s office did not respond to multiple requests for comment, but Ford’s former chief of staff Mark Towhey said in an e-mail that he stands by his earlier assertion that Ainslie’s version of events is “inaccurate.”

“No one asked the mayor to leave and no one asked me to ask the mayor to leave,” Towhey said.

In the months that followed, the Scarborough councillor has emerged as an unlikely thorn in the mayor’s side. His casting out was cemented a week and a half ago, with his decision to pull his support for a tax increase to build a Scarborough subway, inciting outrage from the mayor and his brother on the floor of council.

Ainslie resigned from the mayor’s executive a few days later, before he could be fired. Within hours, his constituents were receiving robocalls from Ford informing them that their councillor had “led the charge against building subways in Scarborough.”

On Monday, Ainslie said he planned to file a complaint with the city’s integrity commissioner about the mayor’s conduct.

“I’m here to start the fight against a bully and a liar,” he said.

Councillor Doug Ford did not respond to calls for this story, but he told reporters that Ainslie had “kind of slid to the left a little bit.”

“He has no integrity as far as I’m concerned,” Ford said. “He has the right to vote and I have the right to inform his constituents.”

Ainslie is not backing down. In a letter to the Canadian Broadcast Standards Council on Friday, he said the weekly radio show the mayor co-hosts with his brother — which last Sunday was devoted in part to Ainslie’s subway vote — “should be removed from the airways immediately.”

To some observers, Ainslie’s dramatic departure from the mayor’s corner is pure politicking in advance of the 2014 mayoral race, in which he plans to support Soknacki. But according to Ainslie’s supporters, how the principled Scout leader fell out so severely with the Fords says more about the character of the councillor himself.

“Councillor Ainslie is respected. You know what you’re going to get with him,” said Councillor Kristyn Wong-Tam, a Ford critic who calls Ainslie’s stand against the mayor during the subway debate his “coming out party.”

“I have no idea what’s going to happen to councillor Ainslie, but I suspect he’ll weather the storm.”

Even a year ago, few could have predicted that Ainslie would find himself near the top of the mayor’s hit list.

By all accounts, the two were never close personal friends — Ainslie says before Ford became mayor, their conversations generally revolved around their kids — but his centre-right stance made him a natural pick for the gravy-cutting mayor’s executive committee.

Ainslie voted in line with Team Ford more than 95 per cent of time in 2011 and 2012, according to analysis by Metro’s Matt Elliott, and last September accompanied the mayor on his trip to Chicago.

But the mild-mannered 46-year-old, who cut his political teeth crunching numbers as vice-chair of the budget committee under Mayor David Miller, has never been a yes man, according to Soknacki, who hired Ainslie in 2001 as his executive assistant when he was a councillor.

“He would not be afraid of saying to me, ‘Councillor, it’s your vote, but here is another opinion,’” Soknacki said. “Paul holds his values dear. As unlikely as it sounds, he has said more than once, ‘Well, that’s wrong.’ I would be surprised if that outlook hasn’t continued.”

Raised in east Scarborough, not far from where he now lives with his wife Janet and three children, Ainslie was active in the Scouts movement and spent summers at the local Boys and Girls Club.

He says his political convictions took root at the dinner table, where his mother, a staunch liberal, would often debate with his father, a firm conservative.

“I really got involved in my community, and I was taught to stay involved in my community,” says Ainslie, who started volunteering on election campaigns in his early teens.

When poor LSAT scores dashed his dreams of becoming a lawyer, Ainslie started his own snack food distribution company. In the late-’90s, he became an executive assistant to former Liberal MPP Annamarie Castrilli, after volunteering on her failed leadership campaign.

“I remember going home to my wife and saying, ‘Somebody is going to pay me to do political stuff that I have always volunteered to do. This is pretty cool,’” he said.

Ainslie came to city hall in 2000, and after a brief stint as executive assistant to Councillor Ron Moeser, went to work for Soknacki’s team. He was appointed as interim councillor in Ward 41 in 2006, partly on the promise that he would not run in the upcoming election.

His integrity took a hit when Soknacki announced he would be stepping down, and Ainslie threw his hat in the race in Ward 43.

“When you are a Boy Scout, your word is supposed to be your bond,” fellow candidate Jim Robb, said at the time. “His word wasn’t his bond.”

But Ainslie insists he had no intention of running until he found out Soknacki was quitting, and shouldn’t be held to the precise words he used in his deposition.

He was elected with 39 per cent of the vote in 2006, and re-elected with 61 per cent support in 2010.

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“I didn’t see anything disingenuous with it … I wasn’t trying to lie to anybody,” he says. “Sometimes in politics, people just pick away at you.”

According to Soknacki, Ainslie was “instrumental” in securing the mayor’s attendance at the Garrison Ball, and “had a great deal of anguish” about whether to share publicly what he perceived to have happened there.

Ainslie, who is now speaking more candidly about the ball than he did in the spring, says Towhey told him at the event, before the mayor’s arrival, “We’ve got a problem.”

“He goes, ‘Well, the mayor’s on his way and he’s not quite himself,’” Ainslie said.

Towhey did not respond to this allegation, or comment on the nature of any conversation he may have had with Ainslie that evening.

During dinner, Ainslie says he was approached by several attendees with concerns about the mayor’s behaviour.

“I remember looking at my wife,” he recalls, “and saying, ‘This is the last thing I need to deal with.’”

Even before his decision to go on record about the Garrison Ball, Ainslie, who defines himself as a “social liberal,” says he had fallen out of favour with the Fords over several key issues.

In addition to his unwillingness to support cuts to the fire department, Ainslie said he “ended up in a huge fight with the mayor and his brother” because Ainslie, who was on the hiring panel for Toronto Hydro, refused to dump a candidate that the Fords did not like.

Ainslie claims he also “got grief from the mayor” over his opposition to a casino.

“Just because Mayor Ford likes it, doesn’t mean I have to like it. It’s not a party system,” he says. “So things started escalating.”

But despite Ainslie’s assertions during the subway debate that he could no longer back a transit option that covered less ground and cost twice as much as the light-rail plan, Councillor Denzil Minnan-Wong says he has “never viewed Paul as a fiscal conservative.”

“I’ve seen him add money to the budget and we’ve lost important votes that he was a key person that we needed support from,” said Minnan-Wong, a Ford supporter who remains on the executive even after voting against the subway plan.

Adam Chaleff-Freudenthaler, a left-leaning activist and former vice-chair of the library board who sparred with Ainslie over library funding in 2011, attributes Ainslie’s break from Ford to the fact that Soknacki, a longtime LRT supporter, has recently emerged as a potential mayoral candidate.

“Paul Ainslie is a bit of a flower to sun. If the sun moves across the sky, he’ll go with it,” Chaleff-Freudenthaler said. “Particularly in a riding like his, where there’s higher income voters, those aren’t the folks that are sticking to Rob Ford. Those are people looking for a new alternative.”

However, Ainslie contests this claim, noting that he voted for a subway in July after Soknacki wrote a column championing the LRT plan.

“I know how to crunch numbers. I love subways, but I think they have their time and place. I just don’t think this particular one is that time and place,” he says.

As Ainslie told reporters on Monday, he believes that not being part of the executive gives him “the independence to speak (his) mind” and “do nothing but stay true to the principles and values” that brought him to city hall.

Ainslie says he would support Soknacki if he runs for mayor, and if not, will look for another “fiscally responsible” candidate with a strong vision for the city.

“I’m not sure whose wagon I’m hitching to next,” he says. “I just know it definitely won’t be Rob Ford.”

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