Regret is a painful thing in sports. Just ask James Dolan. Years after the Knicks passed on Vince Carter due to medical concerns, Carter went on to dominate, leaving Dolan to reflect on what could have been. But was the Knicks’ decision justified, or was it one of the franchise’s biggest blunders?

In a recent interview, it was Dolan who expressed his regret on the New York Knicks missing the chance to land VC. The reason? A severed Achilles tendon, as most fans would have read by now. But how and when exactly did this injury occur?

A closer look at the injury that brought uncertainty over Vince Carter’s NBA career

Carter’s time with the Toronto Raptors had its fair share of highs, but in 2004, things took a worrying turn. ESPN reported in December 2004 that Carter would miss at least two games due to a strained left Achilles tendon. Seeing Carter collapse on the court in visible pain sent shockwaves through the Raptors’ camp.

In Toronto’s 90-86 overtime loss to the Detroit Pistons, Carter went down just as the second half began, leaving fans and teammates wondering how serious it might be. For head coach Sam Mitchell, there was no sugarcoating the impact of losing a player like Carter.

“When you lose one of your starters and star players, it’s always going to be a factor,” he admitted. And he wasn’t wrong. “He’s our best player and he’s out, if he’s out … it’s going to hurt us, there’s no way around it.” The Raptors’ depth was about to be tested, and Mitchell knew replacing Carter’s scoring and presence wouldn’t be easy.

But Carter had battled Achilles issues before. A season prior, he had already missed nine games due to similar troubles. Forward Donyell Marshall, however, wasn’t ready to hit the panic button. “If you look at our guys who were here last year, we played without Vince,” he pointed out, reminding everyone that the team had already found ways to win without their star.

The injury itself was brutal—Carter drove along the baseline, pulled up, and collapsed. He was helped to the locker room and later limped to the team bus, raising even more questions about his future.

Although Dolan did not give any timeline in his recent statement, this incident seems to be it, considering he was traded to the New Jersey Nets by season 2005.

What exactly has James Dolan said of his regret regarding Vince Carter

Years later, Dolan still finds himself haunted by the decision. Watching Carter dominate in New Jersey was a constant reminder of the opportunity that slipped away, not because of finances or trade complexities, but because of a medical misjudgment that proved completely unfounded.

During a Thursday appearance on the Roommates Show podcast with Knicks stars Jalen Brunson and Josh Hart, the team’s executive chairman James Dolan opened up about the one trade he wishes he could go back and make—bringing Vinsanity to New York. But according to him, the Knicks’ medical team had other ideas.

As Dolan recalled, the team was all set to acquire Carter until their medical staff delivered some alarming news. They claimed Carter had a “90 percent severed Achilles tendon” that wouldn’t hold up in the long run.

“And once it ruptured, he’d never be the same player. And for that reason, we didn’t do the trade,” Dolan explained in an article by NY Post, though he didn’t specify when exactly this deal was supposed to happen. The Knicks’ medical staff had convinced Dolan that Carter’s Achilles was a ticking time bomb. But as Carter’s trajectory thereon forced Dolan to confront an uncomfortable truth – his team had gotten it completely wrong.

“Vince Carter went on to have five, six, seven years. I kept waiting for his Achilles tendon to break, it never broke,” he said. Then, with heavy sarcasm, he added, “Yup, we certainly dodged a bullet there, didn’t we?”

The Toronto Raptors traded Carter to the then-New Jersey Nets on December 17, 2004. The Raptors got Alonzo Mourning, Aaron Williams, Eric Williams, and two first-round picks in return. A package that even Carter himself found underwhelming.

What followed was a dominant stretch for Carter in New Jersey. He played over four seasons with the Nets, leading them to the playoffs three times. His 2,070 points in the 2006-07 season still stand as a franchise record. And with 8,834 total points, he remains one of the top scorers in Nets history.

In hindsight, Dolan’s regret is understandable. At the time, teams viewed an Achilles injury as a career-altering event. In hindsight, Dolan’s caution seems excessive, but in the early 2000s, a misdiagnosed Achilles tear could derail an entire franchise’s future.

The Knicks chose caution over potential. But in doing so, they missed out on one of the game’s most electrifying talents. Carter’s dominance in New Jersey proved that injury risks don’t always define a player’s legacy. The Knicks’ front office bet against history. Carter made sure they lost that bet.