In the summer of 2000, the Magic pursued three major free agents: Tim Duncan, Grant Hill and Tracy McGrady.
Hill and McGrady signed with Orlando, but the biggest fish got away. Duncan seemingly came close to picking the Magic before re-signing with the Spurs, spurring numerous questions about the saga.
How good would Orlando have been with Duncan and McGrady, especially if Hill stayed healthy in this alternate timeline? How did David Robinson, who cut short his vacation to meet with a wavering Duncan, convince his star teammate to re-sign? And did Doc Rivers, then coaching the Magic, blow their chance at getting Duncan?
Duncan’s long-time San Antonio teammate Bruce Bowen, who now does color commentary for Rivers’ Clippers, on Fox Sports West:
When Tim went out to meet with Orlando, he asked this question: Can family come on the flights to some games? And from what I understand, Doc said no, and that’s where he lost Tim Duncan.
This theory has been floated before, particularly with Duncan’s then-girlfriend (and future ex-wife) Amy Sherrill wanting to join flights.
Maybe Bowen, through his relationships with Duncan and Rivers, has second-hand insight into the situation. Or maybe this is further-removed hearsay. The possibility of the former makes this intriguing.
But these major-life decisions rarely come down to a single factor.
Would Duncan have liked his family to join some team flights? Probably. Did that turn him from the Magic back to the Spurs? That’s a much harder question for anyone – even Duncan himself, who never faced the counterfactual and all the feelings that would have come with it – to answer.