2. Jrue Holiday
The 76ers drafted Holiday 17th overall in 2009. He quickly became a starter and made his first All-Star appearance in 2013. The 22-year-old kept improving, but Philly did not see themselves as contenders. The franchise decided to rebuild and traded the All-Star for the sixth overall pick in 2013 and a 2014 first-rounder.
Holiday blossomed into an elite scorer and one of the best perimeter defenders in the NBA. He has made six All-Defensive teams, earned another All-Star appearance, and just won his second championship. The 6’4 guard won titles in his first year in Milwaukee and Boston to cement himself as one of the best two-way options of this era.
Trading Holiday helped kick off The Process. Philadelphia won 47 games over three years and was all-in on acquiring high draft picks. Holiday did not fit the plan, but the 76ers should have tried to get him back several times since they returned to contention.
There is minimal regret in losing Jrue Holiday. They certainly could have used him, but trading for him would have been costly. Another move stings significantly worse as the Philadelphia 76ers’ chose wrong and ended up without either star player in short order. The franchise also had to watch him lead a conference rival to two NBA Finals.