Year: 1997
Contract: 7 years, $107 million

The NBA lockout during the 1998-99 NBA season did worse for Shawn Kemp than it did for probably anyone else in the league. Check this out: 

The Cavs listed him at 6'10", 280 pounds—a 34-pound increase from the previous season—but then-General Manager Wayne Embry later revealed in his autobiography that Kemp reported to camp at 315 pounds. “He was really very honest about it,” former Cavs coach Mike Fratello recalled. “I said, ‘Shawn, how did this happen?’ He said, ‘Coach, I didn’t think we were coming back.’”

Talk about pretty bad. Kemp was never the same after such a promising first half of his NBA career. He fell out of the league after the 2002-03 NBA season. Just watch Shawn Kemp dunk compilations on Youtube to take away the pain.