Hardwood Houdini
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17 Worst free agent signings in Boston Celtics history

By Andrew Hughes

Hardwood Houdini takes a look at the 17 worst signings in the history of the Boston Celtics throughout the franchise's storied history Mandatory Credit: Cary Edmondson-USA TODAY Sports
Hardwood Houdini takes a look at the 17 worst signings in the history of the Boston Celtics throughout the franchise's storied history Mandatory Credit: Cary Edmondson-USA TODAY Sports /
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Boston Celtics
Boston Celtics (Photo by Focus on Sport/Getty Images) /

Worst Boston Celtics free agent signing No. 10: Sly Williams

Sly Williams could’ve had a much more destructive tenure on the dynastic mid-1980s Celtics had he stayed longer than 38 days. As someone who was rarely accountable during his brief stint in Boston, Williams left the team for periods of time without letting his employer know where he went.

Williams was coming off a successful season in Atlanta in 1984-85, so his behavior cost him a spot in the league — as he ended up playing his last NBA games in a Celtics uniform for just six appearances.

Boston Celtics
Boston Celtics Mandatory Credit: Brian Bahr /Allsport /

Worst Boston Celtics free agent signing No. 9: Tom Gugliotta

Anytime a player averages less than one basket (two points) per game, it’s fair to label that team-player union a failure. Tom Gugliotta was a serviceable second option for much of his career, but by the time he was a Celtic, he had lost many steps.

While he would recover with a more respectable run on the Hawks to end his career, his Boston tenure will go down in infamy.

Boston Celtics
Boston Celtics (Photo by Adam Glanzman/Getty Images) /

Worst Boston Celtics free agent signing No. 8: Vincent Poirier

“Mr. Sexy Pants” Vincent Poirier was a great locker room signing, but he did nothing to help the Celtics cure their big man woes during the 2019-20 season. While he was signed at just $2.5 million, the fact that Danny Ainge gave him a multi-year deal will always be a head-scratcher.

Poirier only lasted one more season after leaving the Cs in 2020, and he now plays overseas. While Ainge hit on Daniel Theis two years prior, his 2019 signing of a European big man didn’t pan out as well.

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