Brad Bradford is a good example. Keesmaat initially endorsed him (he was a former staffer) until her campaign fizzled and he jumped on the Tory train, gaining his endorsement and campaign resources to eke out a council win. Bradford has spearheaded some good projects in Beaches East York, but has also been a Tory loyalist in council, including voting against opening the books on the Gardiner rebuild and against reopening the Scarborough subway debates (I hope he returned his urban planner card afterwards).
I think a lot of liberal/centrist types find Tory inoffensive, and a return to stability after the Mayor Ford fiasco. How a high society Bay Street insider is a "breath of fresh air" is beyond me, but it got him over 60% of the vote in 2018. Even the Toronto Star endorsed him.