Before the social media era, one of the greatest ‘what-if' situations came in the 2000 NBA free agency. After the Orlando Magic signed Grant Hill, they were determined to sign Tim Duncan. Ultimately, Duncan re-signed with the San Antonio Spurs as Tracy McGrady signed with the Magic.
During the Los Angeles Clippers' game against the Phoenix Suns, Bruce Bowen revealed the reason why Duncan did not leave San Antonio as transcribed by Chris Barnewell of CBS Sports:
According to Bruce Bowen, Tim Duncan’s longtime teammate with the Spurs and current play-by-play man for the Clippers, the chances of seeing that happen were far closer than anybody realized. During Wednesday’s Suns-Clippers broadcast, Bowen shared a story about Duncan’s free agency meeting with then-Orlando coach Doc Rivers. Bowen reveals what wound up being a deal-breaker for Duncan in the clip below: “One thing Gregg Popovich didn’t do was screw it up with Tim Duncan. I remember when Tim was a free agent, he was thinking about going to Orlando when Doc was there. … 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”
While the Magic had an opportunity to become a super team, it worked out well for Duncan. As Duncan won four more championships in San Antonio, Orlando could never establish themselves. Although McGrady became one of the league's best players, Hill only appeared in 200 games due to injuries.
Now that all three players are retired, it is entertaining to think about what could have been. While the Magic would have been competitive against the New Jersey Nets and Philadelphia 76ers in the Eastern Conference, the Los Angeles Lakers won three championships in four NBA Finals appearances.