7 players the Orlando Magic gave up on too soon
7. Chauncey Billups
A bizarre place to start, as Chauncey Billups never played a single game for the Orlando Magic. Still, he has the noteworthy distinction of appearing in the season-ending photo for the franchise in 2000.
Billups is probably the biggest miss on this entire list, and the timing at which he joined the Orlando Magic from the Denver Nuggets in 2000 is what led to the unfortunate circumstances that followed.
When traded to the Magic, Billups had a shoulder injury and was on his fourth team in four years.
In other words, he was essentially a draft bust, and this was his last chance to stick in the league. The Orlando Magic let him walk in free agency to the Minnesota Timberwolves before ever playing, and the rest is history.
It is incredible to think that this player would go on to win a championship with the Detroit Pistons only four years later, and was named Finals MVP in the process.
A five-time All-Star, the second act of his career may see him make the Hall of Fame one day. The Magic were the unlucky ones to catch him just before the script flipped on his career.
At that point in the Magic’s history, they had a young roster designed to clear cap room so they could chase Tracy McGrady and Grant Hill (and Tim Duncan) in the summer of 2000. Billups was extra cap room they could cut for that big free agent summer. The team drafted Mike Miller was soon after Chauncey Billups left, and they went 43-39 in 2001.
Had Billups figured it out with the Magic, it would have softened the blow of watching Grant Hill always miss time through injury — not to mention trading Ben Wallace in the sign-and-trade to acquire Hill. The organization would have remained competitive as well.
This would have led to some notable free agents wanting to join (Tim Duncan strongly considered it anyway in 2000), but on the flipside the Magic likely would never have been bad enough to draft Dwight Howard first overall in 2004.