The 20 worst free agent signings in NBA history

NBA #19. Michael Redd: 6 years, $91 million

Former Milwaukee Bucks star Michael Redd was one of the better shooters and offensive guards in the NBA during the early-to-mid 2000s. In fact, during his contract year in 2004–05, Redd averaged a then-career-high 23 points per game, leading the Cleveland Cavaliers to heavily recruit Redd to pair him with LeBron James after his second season.

Redd opted to stay in Milwaukee, agreeing to a 6-year, $91 million contract in 2005. While it was seen as an overpayment at the time, Redd was an all-star in his twenties, and the Bucks had no better option than to keep him and hope for the best. For the first half of the six-year deal, Redd actually played very well. In his first season, he averaged 25.4 points per game and scored a franchise-record 57 points in a game against Utah, a record that still stands.

He was even better the following season, posting a career-best 26.4 points per game. Unfortunately, injuries took their toll after year three of his contract, in which he averaged 23 points per game. In the final three years of his deal, Redd appeared in only 61 of 246 possible games. Had Redd managed to stay healthy, he probably would’ve still underperformed his big deal, even after putting up big numbers.

While he was good, he simply wasn’t worth a max contract that paid him around 30% of the salary cap. Factor in that he played in fewer than 25% of his team’s games over the back half of his contract, and it tipped an already questionable deal into negative territory. He ultimately finished his career in Phoenix, marking a disappointing end to an otherwise good career.