#5. Larry Hughes: 5 years, $70 million
After LeBron James’ rookie season, the Cleveland Cavaliers looked towards free agency to try and find him a second option. After striking out on Michael Redd, they landed Larry Hughes. Hughes had a fantastic contract season for the Washington Wizards, averaging 22 points, 6.3 rebounds, and 4.7 assists while also leading the NBA in steals with a stellar 2.9 takeaways per game.
Needless to say, the Cavaliers didn’t get that player. He went from being a rising star to being a serviceable starter and being paid like a borderline all-star. For reference, Hughes ate up between 20.8% and 23.4% of the salary cap over his contract and actually made more than Hall of Famer Tony Parker during that span despite Parker making three all-star teams in that five-year span.
He lasted two-plus seasons in Cleveland before being dealt to the Bulls; he was later traded to the Knicks and then the Charlotte Bobcats. That’s four teams in five years. Hughes averaged an underwhelming 12.7 points on 39.1% shooting, 3.5 rebounds, 3 assists, and 1.3 steals.
Overall, it’s clear that the Cavs overpaid for Hughes, who had an all-time great contract season and duped a team into paying him big bucks. Good for him, bad for Cleveland, which had to trade him for the next player on this list.