17 Worst free agent signings in Boston Celtics history

As the winningest franchise in the history of the NBA along with the Lakers, the Boston Celtics are not often associated with mistakes in the draft, the trade market, or free agency like some of their Atlantic Division luminaries are.

The Nets have become synonymous with taking big swings on aging superstars only to have it all fall apart within a few years. Danny Ainge famously fleeced Brooklyn in 2013 with the Paul Pierce/Kevin Garnett trade, while Kyrie Irving and Kevin Durant played for the Nets for less than the duration of the original contracts they signed to be in Kings County. Across the East River, the Knicks are no better. New York is synonymous with some of the most head-scratching free-agent agreements (Jerome James, Eddy Curry, Amar’e Stoudemire) in the history of the league for any team. Even the 76ers could be burned by James Harden if/when he leaves Philadelphia this upcoming summer less than two years after giving up multiple draft picks to land him.

Throw in the Lakers’ endless free agent gaffes — Timofey Mozgov and Luol Deng spring to mind immediately — and you have a league that has seen numerous big market front offices spend recklessly and make fools of themselves in the process.

The Celtics haven’t made such famous mistakes, but their history isn’t flawless either. In honor of Boston’s 17 championships, Hardwood Houdini takes a look at the 17 worst free-agent signings in franchise history:

Worst Boston Celtics free agent signing No. 17: Gordon Hayward

While it’s difficult to blame Gordon Hayward too much for how his Celtics tenure went — he had a season-ending injury within his first few minutes of his debut in green — his max contract signing was supposed to provide the final piece of a core that also included Kyrie Irving, Al Horford, Jayson Tatum, and Jaylen Brown that would bring Banner 18 to Beantown.

Instead, he was the clear sore spot and someone who was out of place his entire time in a Celtics uniform.