Worst free agent signing in Boston Celtics history — Antoine Walker
6 years, $71 million
Over the years after the retirement of Boston legends such as Larry Bird and Kevin McHale, the Celtics struggled to maintain relevancy in the league. Star players eluded them, and fans of the team were desperate for someone to root for. Enter former Kentucky forward Antoine Walker.
Taken in the 1996 NBA Draft, Walker developed into a player who could fill it up with anyone in the league, taking plenty of shots and making plenty of baskets. By his second season, he was an NBA All-Star, averaging 22.4 points per game for the Celtics. Fans immediately embraced him, as he appeared to fill their need for a star.
When Walker hit free agency, the team prioritized bringing him back and handed him a very lucrative contract for six years, $71 million. It was a deal that paid Walker as a true star, and locked him up for many future seasons to come. It was also the largest deal in franchise history.
By the early 2000s, Walker and Paul Pierce were leading the Celtics back to the postseason after a six-year drought. Walker turned in a few high-level seasons and made it look to fans that he was worth the money. Yet in a city that was used to titles, Walker never came close to delivering; the high-water mark for his time in Boston was the Eastern Conference Finals.
Walker’s scoring began to look like empty calories, and his antics became more irritating than lovable. In what will be a theme throughout this list, the Celtics eventually traded him for a package including fellow bad-contract winner Raef LaFrentz from the Dallas Mavericks. Walker would bounce around the league from there.
Later in life, he would recount the negative spiral he eventually was in as a person, losing his salary. It was a contract the Celtics regretted, and one Walker largely squandered anyway. A losing proposition all around.