Something happened last November that we never imagined occurring in Raptors history. The team sent a jersey to the rafters of Scotiabank Arena for the first time. For almost two decades, we never imagined #15 would be in the former Air Canada Center ever. Especially after the guy who was known as Air Canada in these grounds walked away in a bitter fashion. What ensued was years of animosity between one player and a fandom. 20 years later, almost to the date, Vince Carter had tears in his eyes as he finally left this beef in the past.

Fresh off his jersey retirements in Toronto and Brooklyn, Vince Carter was at the 2025 Fanatics Fest and dropped by Dwyane Wade’s live podcast recording with D’Angelo Russell. Both NBA players had to ask how it felt to have his jersey retired by two franchises, but especially at Toronto.

He started with a little humble brag, “I wasn’t trying to jump over through or around anybody. That’s just what it was.” As if you don’t get nicknames like Half Man, Half Amazing, and Air Canada not posterizing players mid air. He does, however, admit that he didn’t realize the impact he had on fans who watched him play until he was chosen to have his jersey retired.

Carter is one of the seven Nets numbers retired. But for the Raptors, he’s the first. And some would’ve argued if he deserved to be the first or have this honor at all. Especially given how he went from being worshipped in the arena to booed. He acknowledges that past estrangement when he told D-Wade and the audience, “to go through what I’ve gone through and obviously it was a tough time in Toronto going back and forth but that’s where that all came from. That was my first time ever having a true face-to-face interaction with Toronto.”

Carter has had other interactions with the Raptors but not in the best way. He got a hostile reception on his first game back in a Nets jersey and dropped 39 points. For years, Raptors Nation didn’t forgive him and even during his analyst career, rarely appeared on Raptors broadcasts.

His jersey retirement was still polarizing. When the NBA analyst was emotional during his jersey retirement ceremony, it was also about finally making peace with Toronto. “That was my first time and it was on that stage as a jersey retirement. So I never really got to kind of if you would mend our relationship.”

He further said he dropped his tough act at the last minute to show his emotions during the ceremony and absorb the moment he nor the basketball community thought would happen.

Vince Carter showed his real feelings about Toronto

When NBA players have beef with an entire city, it’s rarely pretty. Charles Barkley and San Antonio have a hilarious love hate relationship. But it doesn’t look like Kyrie Irving and Boston would make peace in the future. For a long time, that didn’t seem possible with Air Canada and Toronto either.

In the buildup to the trade to the Nets in December 2004, Raptors fans were losing faith in Vince Carter’s ability to win a championship, especially after he went to his college graduation during the playoffs (which he also addressed with Wade).  Meanwhile, Carter was frustrated with the team for not giving him winning pieces. Fans felt Carter betrayed the city by demanding the trade.

It dug the wounds deeper when the former Air Canada, now Vinsanity, dropped 39 points on the Raptors in his first game back. He’d also do other feats like force overtime, make game-winning shots on the Raptors, beat them in the 2006-07 playoffs. All things the Raptors fans wanted him to do for them.

In 2014, things seemingly mended when Carter, playing for the Grizzlies at that time, received a tribute video at the game. Instead of boos, he got a standing ovation for once. That was just as fleeting. He wasn’t seen on Raptors broadcasts (which will change soon now that he’s on NBC starting next season). Raptors nation didn’t fully agree with his jersey retirement either.

Carter though decided he wasn’t going to extend this attitude. Understanding the privilege of this moment, he revealed his decision when he returned to Toronto. “I’mma live in this moment, man.’ Like, all that I’ve gone through, I’m… we back. We back on the uphill. Like, I’mma enjoy it.”

Vince Carter and Toronto really might be uphill once more. Now he’s going to call games at NBC and how that goes in the Toronto region remains to be seen.