You can't make an omelette without breaking some eggs, as they say. If there's one team that has lived by this saying, it's the Boston Celtics. Under Danny Ainge and Brad Stevens, Boston has not let sentiment get in the way of their decisions in the front office.
Because of that, they have made trades that have come off as heartless from the moment they were announced. In the end, these deals could be justified, but that didn't make it less painful to stomach when they happened.
When Boston pulled off trades like these, the fans more or less had this reaction to each and every one of them:
Title teams are rarely built on sentiment, nor do they stay on top on sentiment. Even if the trades made sense, the fans' attachment to these players upset them greatly when Boston decided to part ways with them.
6. Celtics trade Kendrick Perkins to Oklahoma City (2011)
At the 2011 NBA Trade Deadline, the Celtics had a bit of a conundrum. With Marquis Daniels out for the season, they were one of the NBA's oldest teams in need of help along the wing. The fans trusted that Ainge would get such a deal done, and he rewarded them for it, but they didn't think for a second that it would be Perkins who would be sacrificed to make it happen.
Perkins had established himself as a key cog of the Celtics since the Big 3 formed. Even though the Celtics still played elite basketball without him, no one thought he was on the market. However, because the Celtics looked awesome with Shaq filling in for him, and because of Perkins' contract demands, Ainge made one of his riskiest moves.
This destroyed the fans and the team itself, as Perkins was also well-liked in the locker room. The rationale for the deal made sense, but because Boston never quite re-found its footing post-trade, their season was ruined.
This maybe would be ranked higher if Perkins hadn't burned the bridge with the organization in the years following since the deal.
5. Celtics trade Antoine Walker to Dallas (2003)
When Ainge was first hired by Boston in 2003, his intention was to build a title contender, even if it meant trading away a fan favorite. He made a statement right away when he traded Antoine Walker to Dallas shortly after the Celtics hired him.
Walker was not a perfect player, but he was pretty beloved in Boston. After the team went through as much turmoil as it did following Larry Bird's retirement, Walker and Paul Pierce finally started a new era of fun playoff basketball. The Celtics weren't title contenders, but they were good again. Walker was not just good, but fun to watch.
But then, Ainge cut it all short by dealing Walker to Dallas. Many were flabbergasted, including Walker himself, who called Ainge a "snake" for dealing him away. To see Boston hurt their ceiling by trading someone who the city was attached to was pretty off-putting. Little did we know it was the first domino towards assembling the Big 3.
Ainge had the right idea in mind because Pierce and Walker had reached their peak together, but it didn't make the next few years any easier to sit through.
Note: It was very hard to rank the next four on this list.
4. Celtics trade Kevin Garnett & Paul Pierce to Brooklyn (2013)
That should show you just how hard it was to rank these because, sentimentally, Boston trading Garnett and Pierce after all they had done for the Celtics was quite the emotional gut punch when it happened.
Many fans had hoped to see Garnett and Pierce ride into the sunset together as their NBA careers headed towards the end point. In all fairness, they hoped Ray Allen would be there with them. However, Ainge had different plans.
Ainge showed yet again that he didn't care about how attached the fans were to KG and The Truth. What he wanted more than anything was to put the Celtics in the best position to succeed again, so a trade like this was necessary, even if it was painful to see Garnett and Pierce (especially Pierce) in a different uniform.
So why isn't this higher? Because the writing was on the wall that it was time to shake things up. Garnett and Pierce weren't bad in their final year as Celtics, but it was clear they weren't among the NBA's best players anymore. In fact, they weren't even close.
In all fairness, this turned out to be arguably Ainge's smartest move when it was all said and done.
3. Celtics trade Marcus Smart to Washington (2023)
Garnett and Pierce being traded broke hearts, but after they came off a "meh" season with no way of getting better with them, it made sense that they were traded. Smart was a different story. Hours before he was traded, everyone knew Boston was trying to finalize a trade for Kristaps Porzingis, but the main piece going away was Malcolm Brogdon.
Brogdon was awesome in Boston, but there wasn't much attachment to him, as he showed why he didn't cost the team much when he got hurt at the worst possible time. Because there was plenty of attachment to Smart, the last-second twist that he was being sent out instead of Brogdon hit like a nuclear bomb.
Smart embodied Celtics culture because he never took a play off. A star, he was not, but Smart proved he was a game-changer for Boston from start to finish. Everyone had hoped he would get a title from his time in Boston.
So, seeing him get dealt for Porzingis stung like a mother. The rationale wasn't just getting KP, but also believing Derrick White was the better player going forward (they were absolutely correct), but many thought Smart was a Celtics lifer. Knowing he wouldn't be was difficult, even if they won Banner 18 because of this trade.
2. Celtics trade Jaylen Brown to Philadelphia (2026)
Everyone had also hoped Brown would finish his career where it started, as he became one of the best Celtics stories in franchise history. Brown was also coming off his best season as a pro statistically when Boston needed him to do just that.
But Stevens has other ideas. Brown was in line for an even bigger pay raise, which Boston didn't want to meet. Plus, it was clear that despite his talent and his numbers, he was never a perfect fit for Joe Mazzulla's coaching style.
But what makes this especially heartbreaking was to see him get traded to a division rival. We knew Stevens was trying to get rid of him weeks before he did, but we did not think it would be to Philly or for Paul George and two first-round draft assets.
1. Celtics trade Isaiah Thomas to Cleveland (2017)
You may or may not have seen this coming. When it happened, no one would have thought IT, who made himself a Celtics legend in his own way over the past two and a half years, would have been available. However, Ainge had the chance to get Kyrie Irving, i.e., make the Celtics better while making the Cavaliers, their main East competition, worse.
Celtics fans were very attached to Thomas, even if they knew Boston wasn't winning a title with him. His explosive scoring despite his small stature made him one of the most entertaining watches the Celtics had ever seen. More than that, Boston was winning more games because he was leading the charge.
Thomas isn't the best player on this list, but when this went down, many were quite shocked at how cold Ainge was when it came to trades. Thomas fought through an injury and his sister's death for the Celtics. To see them trade him after his devotion to the team made everyone sick to their stomach.
Ainge was right about Thomas, but wrong about Irving, which made it look worse. He likely would have traded IT anyway, but that was an unforgettable experience that got cut down because Boston went for a clear upgrade that sadly blew up in their face.
It's amazing to think that Boston has since made multiple trades that hurt internally like the IT trade did, but still haven't topped it in terms of heartbreaking overall.
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