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Will Tory face stronger opposition from the Left or a right-wing populist in the next election?

With Tory being well liked by the left, centre and even some of Ford Nation, does anyone want to challenge him?
The NDP always has someone run out of principle. From my few visits to council Layton and Cressy stood out as potential flag bearers. I also think Doug Ford will give it another go, if not next election then the one after if Tory doesn't run for a third term. You think Dougie would be the favourite without Tory in the mix?
 
Short of going full religious schools in the next two years, Tory should have this one in the bag. He's already committed to max 1 re-election so any councillor hoping to keep a seat in the chamber will pass. He could, however, face competition from a non-sitting politician as prep for 2022.
 
I doubt Tory would run again in 2022. He'll be in his late 60's by then.

That's what everyone in Ottawa thought about Bob Chiarelli. Of course, then he ran again (and lost to O'Brien, our much more tame Ford-type) in 2008. Even then he could not stay out of politics, ran provincially, and is a Liberal Minister again, presently in his mid-70s.
 
I don't think the NDP/Left will run anyone. It would be an uphill fight, and the last thing the NDP team needs in Toronto these days is another defeat, especially since the next provincial election is tentatively scheduled for June 14, 2018 (four months before the next municipal election). I think the NDP's resources will be focused on winning back ridings like Beaches-East York, Davenport and Trinity Spadina at Queen's Park, rather than tilting at windmills at City Hall.

I agree with @mjl08 - to the extent that the NDP/Left looks to make gains at City Hall, they will target certain wards. Someone like Cesar Palacio is an obvious target. Certainly more reasonable than aiming for Tory.

ETA: I also don't think Dougie will run again municipally. I doubt he has any interest in being Ward 2 Councillor (he had very little interest in the job when he actually had it), and while I think being Mayor would feed his ego, he's already run for the job and lost and I don't think his ego could risk a second loss. To the extent that politics is still in his future, I think he'd aim for Queen's Park. If Dougie were to run for Ward 2, it would all be about family legacy and I don't think his heart would be in it.
 

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