The big issue has always been taxes (for Toronto) and small ridiculous things (Antonio Davis claiming he wanted his kid to learn American History, players complaining about no ESPN, etc). The city seems to of grown on NBA players, sort of a landmark that we could keep Derozan when his hometown of LA was after him. Not a fan of him at all (musically, even if I'm a huge hip-hop head) but Drake has made Toronto cool among NBA guys. Derozan was pretty much the Stamkos situation in reverse.Agree Its completely different. Toronto has big €€€€€€€ everything and is a bit warmer, wayyy more people, cheaper flights / closer to a lot of major US cities, etc.
Toronto does have the odd problem with MLB and NBA players but not too bad and will change as the city establishes a winning pedigree. For NHL its the richest franchise in a huge city can't see why Americans would complain.
Leafs biggest problem is just the terrible culture of losing (not saying Jets don't have this either last 6 years). I think they've had enough and since the Babcock/Lou scorched earth policy following the 2014-2015 season things gonna change.
Love Winnipeg but can be a hard sell for lots of people. Pretty lame IF thats why Trouba is leaving but what can ya do. Just wish it was all taken care of earlier.
At the end of the day, every Franchise is going to want guys who want out for various reasons. Boston, a great city to live in if you are young and have money has had Kessel and Hamilton force there way outs. The myth all Americans want out of Winnipeg should be quashed by the fact Wheeler and Buf stayed, but the guy who left was a western Canadian, and the one who most vocally wanted out (outside fo Trouba) was a Vancouver kid. Maybe its just those Minnesotens, but that is a pretty large pool of American players. It could just be Trouba doesn't trust Maurice.