In the summer of 2010, Boston Celtics guard Ray Allen faced a major decision. As an unrestricted free agent, he had the opportunity to explore offers from other teams.

NBA fans — especially Celtics supporters — know he ultimately re-signed, staying for two more years on a deal worth around $20 million. A few months later, Allen explained why he chose loyalty despite the allure a potential exit had held.

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Allen’s 2010 choice

“The grass isn’t always greener on the other side” — this perfectly captured Allen’s decision-making during the 2010 NBA offseason, when he was considered one of the hottest commodities on the market.

NBA teams usually prize veteran presence in the locker room, players who understand their roles and those with proven championship pedigree. Allen, in his mid-30s, one of the game’s all-time great shooters and a key member of Boston’s 2008 championship squad, checked every box.

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He was drawing interest from multiple suitors, reportedly including the Chicago Bulls, Cleveland Cavaliers, Miami Heat and New York Knicks.

The Celtics were too fully aware of his value. Determined to keep the sharpshooting guard, their front office made securing Allen’s return a top priority after the 2009–10 season had ended with a 4–3 NBA Finals loss to the Los Angeles Lakers.

When a “great” situation suddenly shifts

Allen faced a dilemma familiar to many: leave a comfortable, successful situation for something new and uncertain or stay and value what already worked. He later reflected on why he chose the latter when it came time to put ink to paper.

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“I want to look up and have guys I can count on every single night. I have a chance to be a part of something special,” explained Allen, per ESPN. “You just don’t give up a great situation. You have great teammates. Selfishly, I could have gone somewhere and put up a lot more shots and possibly had a great chance of making a couple of all-star teams.”

It’s safe to say the contractual commitment of the rest of the Big Three — Kevin Garnett and Paul Pierce — and head coach Doc Rivers played a major role in Allen’s decision to re-sign at the time.

While Celtics fans certainly enjoyed seeing him with the team for two additional seasons, it’s interesting how much Allen’s perspective on his situation in Boston shifted in the following years.

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In the aforementioned interview, Allen had clearly described his situation as “great,” preventing any doubts about leaving the iconic franchise he, a former Seattle SuperSonics and Milwaukee Bucks player, had joined via trade in 2007.

However, when Allen later reflected on why he eventually left the C’s in 2013, he painted a very different picture of his situation. Speaking to the Boston Globe, Allen described feeling massively undervalued by the front office, which he said ultimately prompted his move to the rival Miami Heat.

Whether Allen simply revised his view to justify his controversial departure or the Celtics’ environment genuinely deteriorated that quickly is difficult to judge — a question likely only he, a Hall of Famer since 2018, can answer.

This story was originally reported by Basketball Network on Sep 21, 2025, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.