11 Players the Celtics never should have gambled on

The Boston Celtics regretted acquiring these talents.
Boston Celtics, Kyrie Irving
Boston Celtics, Kyrie Irving / Gary A. Vasquez-USA TODAY Sports
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7. Jeff Teague

The Celtics signed Teague to give them a veteran backup point guard behind Kemba Walker. After struggling with injuries in year one, there was no guarantee Kemba would be healthy. Boston had made the conference finals in three of the last four years and wanted a championship. They knew they needed a trusted veteran to turn to if Walker went down.

Teague was an All-Star in 2015 and spent eight years as a starting point guard for three different teams. The 6’3 guard was never a superstar, but a quality option who helped his team reach the playoffs nine straight years.

Things never worked in Boston. Teague was on the decline and did a bit too much stat hunting. He only played in 34 games before the Celtics cut bait as he produced a negative value over replacement player (VORP) in the process.

Teague was traded to the Magic at the deadline before being waived and landing in Milwaukee. The Bucks won the championship in his final NBA season with the veteran playing a limited role off the bench. Jeff Teague’s time in Boston did not work out as planned for either side, but both sides landed on their feet after their split. Teague won a ring in 2021, and the Celtics made the NBA Finals the following year.