Hard to say what he will do after being in the transit sector for 33 years and has a nice retirement plan based on where he work for the position he held.
Surprised he leaving TfL after a short stay as the new position this year considering it was his swan job after NYC. More the fact he moving to the US when he is an Brit and his wife is US citizen. Still a young person with a lot of years to go before 65 to fully retire, then it could be the new 70's years.
Yes it would be nice to see him here again for another 5-10 years.
His wife is a Canadian Citizen, born in Ottawa. I know they do intend to return to the U.S. and be based there for the foreseeable future; but I'm uncertain about whether she (or he) may hold U.S. citizenship.
Personally, I would love to see Toronto woo him as City Manager, boss of every program, and the TTC too.
He couldn't micro manage everything; and wouldn't. But what he would do is demand people be accountable the way he was at the TTC or elsewhere.
No hiding behind the City's PR dept; or ducking the media. That alone would be a useful endeavour.