The 20 worst free agent signings in NBA history

#15. Juwan Howard: 7 years, $105 million

As a member of Michigan’s famed “Fab Five,” Juwan Howard proved worthy of the Washington Bullets taking him with the 9th overall pick in the 1993 NBA Draft. He made an immediate impact, including averaging 22 points per game in just his second season. When it came time to pay him, the Bullets didn’t hesitate to give him a 7-year, $105 million contract.

Perhaps they should have. While Howard had a good career, he never became a player worthy of signing a $100+ million contract. Actually, considering he made $15 million on average over the life of that contract, with inflation, it would be the equivalent of a $200 million contract now.

Worse yet, the salary cap back in 1995 was only $40 million, meaning he ate up more than one-third of that, which is effectively a super-max contract now. To Howard’s credit, he did average 17.3 points, 7.2 rebounds, and 3 assists in 503 games over the life of that contract, but he never made an all-star or all-NBA team during that seven-season stretch. Imagine being stuck paying a merely good but far from an elite player for seven seasons—not great.

Contracts like his led to the NBA lockout in 1999, with owners fighting to save themselves by limiting the length of contracts to six seasons instead of seven. Had that rule not been changed, teams’ fan bases would still be saddled with albatross contracts, so, in a way, his terrible contract helped save the NBA.