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Toronto Mayor Rob Ford listens to a presentation during the executive committee on core service review July 28, 2011 at City Hall.

Toronto is losing its chief labour negotiator on the eve of what's expected to be the toughest test of employee relations since amalgamation.

Jim Vair, the city's director of Employee and Labour Relations, tendered his resignation on July 26, swapping the clamshell for Queen's Park, where he'll work as the chief education labour relations officer for the Ministry of Education.

His departure leaves a void in the city's labour relations team at a time when portents of layoffs, lockouts and labour action loom over City Hall, and continues a slow exodus of Toronto's upper management since Mayor Rob Ford took office.

"I think if I were an experienced labour relations person looking at the prospects ahead I might be inclined to leave the city, too," said Councillor Janet Davis, a former member of the Employee and Labour Relations committee.

Mr. Vair took up his post with the city in 2009, just as negotiations began with its two biggest municipal unions, CUPE Locals 79 and 416, culminating in a 39-day strike.

Since those days of closed day cares and the scent of rotting garbage wafting over the city, Mr. Vair said he has endeavoured to patch up things with the unions.

"We've been working to develop better ties with the unions," he said. "That's probably one of my greatest accomplishments."

But the truce ended with the election of Mr. Ford last October. He campaigned on a promise to contract out the city's garbage collection and wring deep concessions from the unions. He is slowly pushing the former through council, but the latter will have to wait until Dec. 31, when contracts with Locals 79 and 416 expire.

Members of his inner circle have indicated that the city will push to delete an iron-clad provision that guarantees city workers another municipal job if their position is contracted out. The mayor himself has stated that the city needs to shed "thousands" of workers through buy-outs and layoffs.

"The next round of negotiations will probably be the toughest negotiations we've seen since amalgamation," said Public Works chair Denzil Minnan-Wong, who consulted with Mr. Vair as he shepherded the first phase of the garbage privatization plan through council this year. "We're trying to deal with fiscal and financial problems that many previous councils have ignored or swept under the carpet. And this mayor wants to deal it. We'll need skilled negotiators."

Mr. Vair said the prospect of a bruising round of negotiations had nothing to do with his decision.

"Everything coming down the pipe at the city is challenging, but labour relations in the public sector has never been anything but challenging," he said. "As much as the speculation about my departure may be tied with things going on at the city, it is simply because of a unique opportunity that's come along in the sector I want to be in."

Mr. Vair returns to a familiar field. He worked at the Waterloo Region District School Board and Queen's University before coming to Toronto.

His exit marks at least the sixth departure of a top city manager since Mr. Ford took control of council, a slow drain that has alarmed some councillors.

"It's worrisome how we're losing very talented senior management," said Ms. Davis. "Jim will be a big loss to the city. He took balanced positions on things and recognized that positive environment was necessary if you're going to negotiated a successful collective agreement."

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