The 30 most painful NBA Draft pass-ups since 2000

Greg Oden #20 of the Miami Heat on the bench during an NBA game (Photo by Christian Petersen/Getty Images)
Greg Oden #20 of the Miami Heat on the bench during an NBA game (Photo by Christian Petersen/Getty Images) /
30 of 31

NBA Draft Mistake #2: Detroit drafting Darko Milicic over Carmelo Anthony, Chris Bosh, and Dwayne Wade.

The 2003 NBA Draft is widely regarded as one of the greatest ever. In fact, five of the first six picks made at least one NBA all-star team, and four of them will all likely make the Basketball Hall of Fame. Unfortunately, the Detroit Pistons were the sole team with a high lottery pick that failed to come away with an all-star caliber player after they infamously gambled on Darko Milicic.

With an influx of talented international players such as Gasol and Parker, the Pistons chose to gamble on the unknown in hopes of finding their next star post-Grant Hill. They bet wrong and passed up on Carmelo Anthony, who had just led Syracuse to a national championship in his only season there, as well as Chris Bosh and Dwayne Wade.

The Pistons’ blunder didn’t appear to hurt them in the short term, considering they won a championship in 2004 and lost in Game 7 of the NBA Finals in 2005. They also had the best record in the NBA in 2006, en route to a third of six consecutive Eastern Conference Finals appearances. Then again, had they gone with the far safer option in Anthony, they would have added a highly gifted scorer to a team known for their defensive prowess.

That might’ve put them over the top in at least some of their Eastern Conference Finals series, and maybe they would have won more than one championship with those Bad Boy Pistons II teams. That might have convinced Melo to stay put in Detroit rather than demand a trade to the New York Knicks.

That would have dramatically changed NBA history, including the 2023 NBA Finals, with Denver using the pick swap received in the Carmelo Anthony trade to draft Jamal Murray. Ultimately, had Detroit not made the mistake of drafting Milicic, they could have won more championships than they did and avoided the 15+ year hangover since their last deep playoff run.