In his prime, Tracy McGrady was regarded as one of the NBA’s greatest scorers. However, his legacy has always been peppered with “what ifs,” with many believing his career could have reached even greater heights had he played alongside a dominant force in the paint, like Shaquille O’Neal. There’s also a lesser-known chapter involving another generational talent, Tim Duncan.
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On Timeless Sports, McGrady recently recalled a story from the year 2000, when the Orlando Magic were assembling a formidable core with Grant Hill and himself. They were poised to chase the best record in their conference and potentially a championship.
Duncan was a free agent, weighing his options across the league. The Magic quickly emerged as front-runners to land him. He had already won a title and a Finals MVP in 1999, and Orlando looked like the perfect next step. A dinner meeting was then set up with the organization, but alas, the deal collapsed, and Duncan chose to remain in San Antonio. Per T-Mac, one specific disagreement killed the move.
He said, “I guess, the question came up about his spouse being able to travel with the team. And Doc Rivers [coach of the Magic] turned that down. I think that was the deal breaker for Timmy not to sign with us.”
McGrady never understood why Rivers denied Duncan’s request, as it wasn’t really a difficult thing to say yes to. Had he allowed Duncan’s wife to travel with the team, the Magic’s history could’ve been very different. “You’re supposed to give that man whatever he wants. That’s just the difference in certain organizations and certain personalities to pull the trigger to change the trajectory of your organization,” T-Mac said.
The opportunity to sign Duncan never came back around. But it wasn’t just the Orlando organization that made mistakes during the legendary star’s free agency. The Spurs almost lost him during negotiations as well. As per R.C. Buford, CEO of the San Antonio Spurs, “We probably couldn’t have screwed up worse than we did.”
He knew that Orlando had the charm to attract any player, especially ones with families. Disneyland was a major factor. Apart from that, they also had the draft picks, and Buford was scared he might lose his best player. Some of the decisions they made during that period didn’t help them either. “I think we focused more on trying to convince him that Orlando wasn’t a place for him than we focused on who we were, and the meeting we shared with Tim was a disaster. I mean, I walked out of it, and we blew it,” he said on The Vertical Podcast with Woj in 2016.
Fortunately, despite the disaster, Duncan stayed back in San Antonio because of his relationship with the great Gregg Popovich. That moment still stings for McGrady. His career became a series of near misses: teaming with Duncan and a healthy, superstar-tier Grant Hill. But Hill’s frequent injuries and the lack of a second star beside McGrady left Orlando short.
