If you thought the Ray Allen-Boston Celtics drama is tops on Doc Rivers' list on his worst negotiating failures, think again. Rivers still recalls as a 
“bigger failure” from 12 years ago to Rob Bradford from WEEI.com Green Street:
“I lost a bigger one, and probably learned a lot of lessons from that. Tim Duncan in Orlando,” he said. “We never had him, but I thought we had him turned and we lost him. So I’All always remember that one.”
It's safe to assume that Rivers probably has flashbacks of that lost 2000 offseason opportunity and a few “what could have been's” lingering around his mind. A team with then free agents Tim Duncan and Grant Hill accompanying a young star in Tracy McGrady may do that to a coach. Grant Hill's professionalism and skills partnered with Duncan's “quiet leadership” and his acceptance of being treated the same way as the last player on the bench will do that to a coach. There's no way of predicting that Hill would still be plagued by injuries throughout his Magic tenure and career if Duncan signed, but the possibility of a healthy Grant Hill would've brought unlimited possibilities in a then weak Eastern Conference.
Even with Duncan signing and staying a Spur throughout his career and most likely retiring as one, it worked out well for both sides. Duncan's career has brought him 4 NBA titles, 3 Finals MVP's, 1 regular season MVP, and the title of “Greatest Power Forward of All Time”. Rivers' coaching career hasn't been too shabby either. After being let go by the Magic after the 2004 season, he was brought in by the Boston Celtics as their head coach a year later. He had a superstar in Paul Pierce and during the 2007 offseason, he was given Ray Allen and Kevin Garnett in trades that would promise him at least one NBA title in 2008 in a rekindling of a longtime rivalry with the Los Angeles Lakers.
When Doc Rivers retires, he can look back at a successful coaching career with no regrets. He'll have at least one more opportunity to think of “what could've been” tonight when the San Antonio Spurs play visitor to a hosting Celtics team at the TD Garden. Tim Duncan knows that 12 years later and will continue to show Rivers what he can still bring to the table as one of the league's top big men, even at 36 years old.