Top 10 Worst Contract Year Flops In NBA History

In the NBA, the contract year is supposed to bring out a player's best. It's when motivation, opportunity, and desperation blend to produce career-defining performances that often lead to life-changing money paid by teams hoping to have found their next savior. But for these ten players, the big payday marked the beginning of the end.

1. Chandler Parsons (2016): 4 years, $94 million 

Parlayed two moderately successful years with the Dallas Mavericks into a max contract from Memphis, then played just 95 games over four years due to ongoing knee problems. He never averaged more than 7.9 points per game with the Grizzlies and was ultimately waived.

2. Ben Simmons (2019): 5 years, $177 million 

Signed a max extension after strong early seasons with Philadelphia, but his complete collapse, refusing to shoot, playoff failures, including passing up a wide-open dunk, and chronic back injuries in Brooklyn made his contract a disaster. Averaging just 6.5 points over 90 games in three seasons with the Nets, Simmons last played with the LA Clippers during the 2024–25 season.

3. Bradley Beal (2022): 5 years, $251 million 

Beal secured a supermax contract from the Washington Wizards after averaging 23.2 points.  A three-time All-Star with the Wizards, Beal was then traded to Phoenix a season later, where his production and efficiency declined significantly. One of the few players in the league with a no-trade clause, Beal was bought out by the Suns in 2025 and signed a two-year deal with the LA Clippers. 

4. Allan Houston (2001): 6 years, $100 million 

Houston received a max deal from the New York Knicks after his best season (19.7 points, career-high field-goal and 3-point shooting percentages) and his first of two trips to the All-Star Game. Houston hit the 20+ point average from 2001 to 2003, but then knee injuries slowed his career. He became the poster child for the NBA's subsequently created "amnesty clause," allowing teams one penalty-free contract buyout.

5. Gordon Hayward (2020): 4 years, $120 million 

Hayward opted out of $34 million with the Boston Celtics to sign a fully guaranteed deal with the Charlotte Hornets. Injuries limited him to just 173 games over three seasons, during which his scoring dropped from 17.5 to 14.5 points per game, ultimately leading to a buyout and a signing with Oklahoma City for the minimum.

6. Jerome James (2005): 5 years, $30 million

On the back of one strong playoff series with the Seattle Sonics (12.5 points, 6.8 rebounds), James turned it into a big payday from the New York Knicks. Arriving at his first Knicks training camp out of shape, James then averaged 2.2 points per game over four miserable seasons, perhaps the worst playoff-to-payday ratio in history. He was out of the league by 2008.

7. Rashard Lewis (2007): 6 years, $118 million 

Rashard Lewis got a max contract from the Orlando Magic after nine years in Seattle. After posting back-to-back 20+ point seasons with the Sonics, Lewis had solid but not max-worthy numbers (14–18 points per game) during his three-plus seasons in Orlando. He was traded to Washington and then Miami, becoming a role player and never justifying the massive investment.

8. Timofey Mozgov (2016): 4 years, $64 million 

Timofey Mozgov received a stunning deal from the LA Lakers just days into free agency after back-to-back NBA Finals appearances with Cleveland. Averaging 10.6 points and 7.3 rebounds during the 2015 Finals, he dropped to just 1.2 points and 1.6 rebounds a year later. Despite the fall-off, the Lakers were in desperate need of a big man. He averaged 7.4 points and 4.9 rebounds in one disastrous season before being traded to Brooklyn with D'Angelo Russell just to clear salary space.

9. Patrick Williams (2024): 5 years, $90 million 

Patrick Williams somehow earned an extension from the Chicago Bulls despite showing essentially no improvement from his rookie season, with nearly identical statistics (10 points, four rebounds) five years later. The former fourth overall pick, who has seen his numbers decline each season due to a lack of development and various injuries, makes this one of the most puzzling extensions in recent history.

10. Erick Dampier (2004): 7 years, $73 million 

Erick Dampier secured a massive deal from the Dallas Mavericks after averaging 12.3 points and 12.0 rebounds in his contract year with the Golden State Warriors. Unfortunately for the Mavericks, the big man then never averaged more than 7.5 points or 8.1 rebounds again. He became a cautionary tale about overpaying for career-year bigs.