"That's when he lost Tim Duncan?" - When Bruce Bowen revealed the reason for Orlando's biggest free agency mistake

“That’s when he lost Tim Duncan?” – When Bruce Bowen revealed the reason for Orlando’s biggest free agency mistake originally appeared on Basketball Network.

In the summer of 2000, Tim Duncan, one of the league’s most coveted free agents, faced a pivotal decision: stay with the San Antonio Spurs, his team since 1997, or take his talents to the Orlando Magic.

While fans know the NBA icon eventually stayed in San Antonio, few recall why Orlando lost out. That’s where, in 2017, Bruce Bowen, Duncan’s longtime Spurs teammate, came in, sharing insight into the actual reason.

Team over everything

In professional sports leagues, including the NBA, head coaches often prioritize team cohesion. Success isn’t just about talent — it’s about the group, from the superstar to the bench player, moving as one on and off the court.

On road trips, for example, the team travels together, eats together and stays at the same hotel, unless circumstances make that absolutely impossible.

Furthermore, only the “team,” as the name itself suggests, is allowed on the team plane. After all, additional passengers — such as family members or partners — can disrupt the cohesion and focus that define a true squad dynamic. As a result, anyone wishing to support players during away games must make separate travel arrangements.

It might sound harmless enough, yet this is where the key detail in the Magic-Duncan saga emerges, at least according to Bowen.

Commentating on a Los Angeles Clippers–Phoenix Suns game in 2017, the former small forward revealed that during Duncan’s free agency period, he asked if that rule could be bent — a request then-Magic head coach Doc Rivers ultimately denied.

“When Tim went out to meet with Orlando, he asked, ‘Can family come on the flights to some games?’ From what I understand, Doc said no, and that’s when he lost Tim Duncan,” said Bowen.

What if?

Some might see Rivers’ rigidity as fumbling one of the league’s premier forwards, a Finals MVP who was putting up 21 points and 11.4 rebounds per game at the time.

Others might view it as a statement of principle. For the 2000 Coach of the Year, no exceptions were allowed — not even for a future Hall of Famer like Duncan. Star treatment and special privileges simply weren’t on the menu.

Either way, Timmy stayed in San Antonio, adding three more rings to the one he had already won in 1999, while Orlando remains without a championship title. It’s fair to say that if the two-time MVP had joined the Magic, who had ample cap space, the landscape of the league could look very different today.

Duncan, alongside Grant Hill and Tracy McGrady, who came over in August 2000, would have formed a true Big Three, capable of reshaping the league and even potentially launching a dynasty.

If that thought is not enough for Magic fans to stomach, consider Duncan’s own reflections after visiting the Florida-based franchise.

“Orlando had a lot to offer,” he reflected in July 2000, per ESPN. “I went down there and had a good time.”

While that was certainly true, hindsight shows the 15-time All-Star made the right call to stay with the Spurs.

The decision elevated his individual and team accolades, and even allowed him to be occasionally joined by family on San Antonio’s team plane — a courtesy likely granted by then-head coach Gregg Popovich, but never extended by Rivers, who is now with the Milwaukee Bucks.

This story was originally reported by Basketball Network on Aug 20, 2025, where it first appeared.

“That’s when he lost Tim Duncan?” – When Bruce Bowen revealed the reason for Orlando’s biggest free agency mistake

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