From an urbanist perspective, the Gardiner being rebuilt is a terrible decision. If it gets uploaded, wave goodbye to streetscape improvements [MTO is terrible] and any potential of tolling in the medium term.
From a wily political perspective, I can see why the province uploading the DVP and Gardiner could be good thing. Ford (and his allies in Council) get to claim "we saved the Gardiner", as well as supporting their construction industry and auto lobby pals.
Chow doesn't have to have the fight in council over it (not a guaranteed victory), no longer has to spend $1bn+ on rebuilding the Gardiner (potentially money that could be spent elsewhere), and potentially gets a "hall pass" for something else with Ford. You scratch my back, I'll scratch yours.