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Ontario’s premier-designate, Kathleen Wynne.

Fred Lum/The Globe and Mail

Ontario premiers (and wannabe premiers) have a habit of distancing themselves from Toronto. In December, Sandra Pupatello of Windsor described Tim Hudak as "too Toronto" to lead the province and told her fellow Liberal leadership candidates to look beyond the city they lived in: "I need my colleagues … to know that there's a big old province out there," she said in a debate.

Enter Kathleen Wynne, Richmond Hill born-and-bred.

She learned the political ropes under the tutelage of John Sewell, arguably Toronto's most leftist mayor. She fought amalgamation. She worked directly with the Toronto District School Board. She put David Crombie, another one of Toronto's left mayors, on her transition team – that's two former liberal mayors guiding her. She lives and breathes Toronto and it's clear it will be at the top of her policy agenda.

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"She's bound to have a greater and deeper understanding of Toronto than Dalton McGuinty," said former provincial Progressive Conservative leader John Tory, who was defeated by Ms. Wynne in the 2007 election. "She will have an advantage because she was here for many, many years and steeped in these issues."

Just two days after her Liberal leadership convention win, Ms. Wynne was at the Metro Toronto Convention Centre with many of the city's leaders for the Toronto Region Board of Trade's annual black tie gala dinner. Ontario's premier-designate spent her evening at the most buzzed-about table, gabbing with Mississauga mayor Hazel McCallion, who sat beside her, and Toronto mayor Rob Ford, a few seats over.

The woman who cut her political teeth in the anti-amalgamation movement – now holding court with the megacity mayor from Etobicoke?

"If anybody will be able to give a first-class effort to build bridges to help folks get services they need, it'll be Kathleen. I have no doubt about it," said Mr. Crombie, who first encountered Ms. Wynne when she was an anti-amalgamation activist in the nineties.

Ms. Wynne's predecessor, Dalton McGuinty, had strained relations with Mr. Ford, due in part to the mayor scrapping the transit plan Mr. McGuinty had agreed to with former Toronto mayor David Miller before being overruled by council and reverting back to the original plan.

This week, Ms. Wynne told media she had "a very nice exchange" with Mr. Ford at the Board of Trade dinner and the mayor was keen to meet either on his turf or hers. Still, she'll be competing with the province's opposition leader, Tim Hudak, who shares the mayor's love for subways and made an appearance at the mayor's annual backyard barbecue in 2011.

But Ms. Wynne has a reputation for consensus building – before entering politics, she worked as a professional conflict mediator.

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Even her old political foes say she has a knack for maintaining respectful communication in hostile situations.

"I don't think there will ever be a bond between [Ms. Wynne and Mr. Ford] but there could be an understanding that it's in their mutual best interest to get some things done for Toronto on, say, transit in particular," said Mr. Tory.

"I watched her when I was across the house from her, I watched her when I questioned her, I've watched her since and she's just not a phony," Mr. Tory said. "I think her seeming authenticity … will make for a better relationship."

One certainty for Ms. Wynne is an easy relationship with Ms. McCallion. While Mississauga South MPP Charles Sousa was dubbed the "queenmaker" at the leadership convention, political watchers say Ms. McCallion may have been the real power broker on Saturday. Many say her presence in Ms. Wynne's camp influenced Mr. Sousa to throw his support behind Ms. Wynne. With two fellow Mississaugans also vying for party leadership, Ms. McCallion's unofficial endorsement of Ms. Wynne sent a strong message.

"That took a lot of gumption, which doesn't surprise me on Hazel's part, but I think it was also an important signal that she thought Kathleen Wynne was the right person," Mr. Tory said.

Developing a constructive relationship with Toronto's mayor will be trickier.

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What gives Ms. Wynne an edge is her long history working on civic matters from the inside – in contrast to all the premiers who preceded her in recent memory.

When former mayor John Sewell started an anti-amalgamation campaign in the nineties, he recruited Ms. Wynne – who shared many of his leftist opinions on major city issues – to play a key role in the movement. She chaired meetings of up to 2,000 people and, unlike her combative counterparts, Ms. Wynne was "the voice of reason and calm," he said.

He wasn't surprised to see her elected to the TDSB and he campaigned for her when she ran for a seat in the Ontario legislature.

Even after moving into provincial politics, her interest in Toronto never waned.

In 2009, the TDSB was on the brink of closing dozens of school pools unless they received the millions of dollars necessary to keep them open. The city refused to pony up and so the Toronto Lands Corporation (a subsidiary of the TDSB) turned to the province. Ms. Wynne worked with the group and helped them eventually get $15.8-million from the Ministry of Infrastructure for the repair of 31 pools.

For Mr. Crombie, who led the group, it was a major victory for Toronto residents. But it was also a glimpse of how Ms. Wynne could effectively navigate provincial-municipal affairs.

"I say it with love and affection: She's a really good politician," Mr. Crombie said. "A really good, democratic representative."

With reports from Kate Hammer, Karen Howlett and Sarah Lilleyman

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About the Authors

Dakshana Bascaramurty is a national news reporter who writes about race and ethnicity. She won a 2013 National Newspaper Award in beat reporting for her coverage of changing demographics in the 905 region. Previously, she was a feature writer for Globe Life. More

Washington correspondent

Adrian Morrow covers U.S. politics from Washington, D.C. Previously he was The Globe's Ontario politics reporter. He's covered news, crime and sports for The Globe since 2010. He won the National Newspaper Award for politics reporting in 2016. More

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