Tracy McGrady's best career highlights came after the Toronto Raptors lost him to free agency. There's the two consecutive seasons when he led the NBA in scoring, the NSFW sonning of Shawn Bradley, and that epic 13 points in 33 seconds comeback win against the Spurs—who'd eventually be the final NBA team he'd play for.
Despite his accomplishments, he of course never made it pass the first round of the playoffs until he rode the Spurs' bench to the Finals last year; we're still mad he didn't score a bucket. McGrady said he should've stayed in Toronto because he believes his squad—which included a young, but ready Vince Carter—had a shot at winning a championship even though this was during the Kobe Bryant/Shaquille O'Neal age. He reminisced on his time at Toronto with the Toronto Star:
In hindsight, looking back, obviously I wish I had stayed in Toronto. There’s no doubt we could have contended for a championship. I think about that often. But if ‘if’ was a fifth, you know?
Had I been a little older and wiser and knew what was ahead of me, I would have stayed, no doubt, with those guys. But that was some of the best times of my life, man. Being with (Charles) Oakley and Kevin Willis and Antonio Davis, Muggsy (Bogues), Dell Curry, Dee Brown. Man. I still talk to a lot of those guys to this day. Because I appreciated how they looked out for me. They were all professionals.
While McGrady flourished as an individual player, the Raptors didn't go too far afterward. Carter and the Raptors battled with Allen Iverson and the 76ers in the 2001 Eastern Conference semis before falling in seven games. Toronto would only make the playoffs three times since then and never make it past the first round. The squad is similar to McGrady in the latter aspect though.
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[via Pro Basketball Talk]