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Remarkably open for a City Councilor, and I am not even his constituent.

I'd imagine you're not coming at him with a established attitude of him "not fit to be a good representative politically". So your results may vary.
 
One interesting thing about the Bradford-Kellway race is that the (more affluent) "old city" half voted to the right of the (more working class) East York part. Usually it's inner city "left" vs. more suburban "right" - progressive politics in Toronto is very "Brahmin left."

ETA: Though I'm guessing old Ward 30 (Beaches part) voted more heavily for Keesmaat than old Ward 29 (East York part).
 
If Tory doesn’t take a run at it, the odds of a populist celebrity candidate go way up. Think Sun columnist or talk radio announcer.

For the left, think disgruntled backbench Liberal MP or defeated MPP.

do any of the current councillors have a city wide machine? None come to mind
 
One interesting thing about the Bradford-Kellway race is that the (more affluent) "old city" half voted to the right of the (more working class) East York part. Usually it's inner city "left" vs. more suburban "right" - progressive politics in Toronto is very "Brahmin left."

ETA: Though I'm guessing old Ward 30 (Beaches part) voted more heavily for Keesmaat than old Ward 29 (East York part).

One interesting thing about the Bradford-Kellway race is that the (more affluent) "old city" half voted to the right of the (more working class) East York part. Usually it's inner city "left" vs. more suburban "right" - progressive politics in Toronto is very "Brahmin left."

ETA: Though I'm guessing old Ward 30 (Beaches part) voted more heavily for Keesmaat than old Ward 29 (East York part).

You don’t have to guess…


 
What did the last two mayors before Tory accomplish? What's Ford's legacy? or Miller's?

Miller decided to quit before getting Transit City irrevocably underway, exposing it to cancelation by his successor and leaving Toronto with over a decade of delay on mass transit. I mostly remember Miller for is foisting giant waste rollie bins onto every home and giving us Fantino as police chief. Well, to be fair Miller's administration did give us the Regent Park redevelopment that has been good for my neighbourhood, so I'll give him that - though it's going to be over 20 years from ideation to completion. Ford will need to stick around if he wants his own Regent Park legacy.

Miller actually helped Toronto get rid of Fantino. Bill Blair was his replacement, appointed during Miller's mayoralty. Blair came in with high expectations, got some reforms done, but blew it with G20.
 
A few other Miller accomplishments:

- Gaining new revenue tools for the city, like the land transfer tax and vehicle registration tax.
- Tower Renewal Program
- Getting BMO Field built
 
Wasn't tower renewal Graeme Stewart's idea?

Yes, he was the brainchild. Miller spearheaded the funding.

 
Inner Toronto results based on the old 44 ward system.

Former Ward 13 (Swansea, Bloor West Village)

Tory 10,315 56.7%
Keesmaat 6,360 35%

Former Ward 14 (Parkdale, Roncesvalles)

Keesmaat 6,810 46.7%
Tory 6,053 41.5%

Former Ward 17 (Corso Italia, Caledonia)

Tory 5,671 52.6%
Keesmaat 3,566 33.1%

Former Ward 18 (Dufferin Grove, Little Portugal)

Keesmaat 6,704 47.9%
Tory 5,368 38.4%

Former Ward 19 (Little Italy, Liberty Village)

Keesmaat 8,035 45.3%
Tory 7,809 44.1%

Former Ward 20 (Annex, Entertainment District)

Tory 10,382 47.3%
Keesmaat 9,366 42.7%

Former Ward 21 (Forest Hill, Wychwood)

Tory 7,891 59.3%
Keesmaat 4,184 31.4%

Former Ward 22 (Midtown, Forest Hill)

Tory 13,212 65.2%
Keesmaat 5,816 28.7%

Former Ward 27 (Rosedale, Church-Wellesley)

Tory 13,210 58.7%
Keesmaat 7,752 34.5%

Former Ward 28 (Cabbagetown, Regent Park)

Tory 10,923 52.5%
Keesmaat 5,468 34.5%

Former Ward 29 (Danforth, East York)

Tory 8,532 55.1%
Keesmaat 5,287 34.1%

Former Ward 30 (Riverdale, Leslieville)

Tory 8,131 50.5%
Keesmaat 6,306 39.1%

Former Ward 31 (East York)

Tory 8,891 60.9%
Keesmaat 3,782 25.9%

Former Ward 32 (Beaches)

Tory 10,511 60.9%
Keesmaat 5,438 31.5%
 
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Given remapping of the central three electoral districts, I've subdivided a few of the old wards.

Former Ward 19

University-Rosedale

Keesmaat 3,449 49.9%
Tory 2,690 38.9%

Spadina-Fort York

Tory 4,464 50.9%
Keesmaat 3,489 39.8%

Former Ward 20

University-Rosedale

Keesmaat 5,219 49.4%
Tory 4,207 39.9%

Spadina-Fort York

Tory 6,175 54.2%
Keesmaat 4,147 36.4%

Former Ward 27

University-Rosedale

Tory 7,306 66.2%
Keesmaat 3,228 29.2%

Toronto Centre

Tory 5,792 50.6%
Keesmaat 4,415 38.5%

Former Ward 28

Toronto Centre

Tory 7,928 50.6%
Keesmaat 5,468 34.9%

Spadina-Fort York

Tory 2,995 58.1%
Keesmaat 1,717 33.3%
 
Does "gentrification" actually hurt the NDP and NDP-ish left in Toronto? Debatable.

I'd say it mostly hurts the NDP, with some exceptions. Based on my observations, there is a large "ABC" Anyone-But-Conservative vote in the gentrifying areas, as these voters will typically vote for the party best positioned to stop the Conservatives. Most of the time, it favors the Liberals. However, occasionally it works in the favour of the NDP, such as the Federal 2011 election or Provincial 2018 election.

In my riding of Parkdale High Park, I would argue that there is a bigger NDP dyed-in-wool "base" than the Liberals, but there is a huge and growing pool of "leftish-flexible" voters who will vote based on the prevailing winds. It also explains why my poll went only 16% Liberal in the 2018 provincial election, but 47% for the Liberals in the 2019 federal election.
 
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