
Shortly after the Boston Celtics disappointing 2021 season came to a close, President of Basketball Operations Danny Ainge announced that he is stepping down after nearly two decades on the job.
While Ainge’s replacement—former Celtics head coach Brad Stevens—has his work cut out for him in improving the Celtics’ roster going forward, we decided to put a wrap on Ainge’s time in Boston by looking back at the five best trades that he made as the Celtics’ President of Basketball Operations.
5. Boston Celtics trade down to draft Jayson Tatum (2017)
When the Boston Celtics landed the number one overall pick in the 2017 NBA Draft, most people assumed that they would select Washington guard Markelle Fultz, who was the consensus top prospect in the draft. However, Ainge pulled a surprise move, trading the pick to the rival Philadelphia 76ers in exchange for the number three pick and a future first round pick.
The Sixers took Fultz, and the Celtics wound up selecting Duke forward Jayson Tatum third overall. Four years later, it seems safe to say that the Celtics won that deal handily. Tatum is already a two-time All-Star, while Fultz is no longer with the Sixers, and he has yet to average more than 13 points per game in a season. In addition, the Celtics used the additional pick that they acquired in the deal to select Romeo Langford, who has become a contributor off the bench.

4. Boston Celtics acquire Isaiah Thomas at the trade deadline (2015)
When Brad Stevens took over as the Boston Celtics head coach during the summer of 2013, the general consensus was that the team was undergoing a massive rebuild, and that it would be several years (at least) before they would even be a playoff team again, let alone a title contender.
But that all changed at the trade deadline in 2015, when Ainge traded for an undersized point guard named Isaiah Thomas.
In just 2.5 seasons in Boston, Thomas etched his name into Celtic lore. He embraced the role of the underdog, serving as the undersized leader of a team without a true superstar. He embraced the City of Boston and took a rebuilding team near the bottom of the Eastern Conference standings and lead them to three consecutive playoff appearances, including a trip to the Eastern Conference Finals in 2017.
Unfortunately, injuries and the infamous Kyrie Irving trade ended Thomas’s time in Boston far too soon. But he remains beloved in Boston to this day, and his legacy lives on through the young players that he mentored, most notably Jaylen Brown and Marcus Smart.

3. Boston Celtics trade for Ray Allen (2007)
The 2006-2007 Boston Celtics season was one of the worst in franchise history.
The team finished with a horrific 24-58 record, and there was little reason to be excited about the future. But that changed the instant that Ainge traded for Allen, a future Hall-of-Famer and arguably the greatest shooter of all time.
Teaming up with Paul Pierce and Kevin Garnett (more on him below), Allen played a major role in the Celtics completing one of the greatest single-season turnarounds in sports history, as they dominated the NBA in 2007-2008 en route to the franchise’s 17th title.
Allen would play four more years with the Celtics after that championship season, helping lead them to within a game of another title in 2010 and a trip to the Eastern Conference Finals in 2012, while also setting multiple franchise shooting records.

2. The Boston Celtics and “The Brooklyn Trade” (2013)
Sadly, all great things must come to an end.
By the summer of 2013, it was clear that Celtics legends Paul Pierce and Kevin Garnett were well past their primes, and that they were no longer capable of leading Boston to an NBA championship. Thus, Ainge had to make the incredibly difficult decision to trade his two aging superstars to the Brooklyn Nets and rebuild the Celtics from the ground up.
What made this deal so impressive was the array of draft picks that Ainge was able to land in return for Pierce and Garnett. The Celtics received three first round picks from Brooklyn, as well as the right to swap first round picks in 2017. While several of those picks have yet to amount to much of anything, Ainge struck gold on two of them in Jayson Tatum and Jaylen Brown.
As long as Tatum and Brown are with the Celtics, this blockbuster deal will continue to live on. And if the two of them are able to bring a title back to Boston, it would certainly put a gold stamp on Ainge’s legacy.
1. Boson Celtics getting Kevin Garnett (2007)
While Jayson Tatum and Jaylen Brown might eventually lead the Celtics to a title, Ainge’s best trade was the one that already has a banner in the rafters as a result of it.
More from Celtics All-Time Lists
- Boston Celtics: An ode to the greatness of Kevin Garnett
- Selecting the Boston Celtics All-Time starting lineup
- Top 5 Boston Celtics draft busts in franchise history
- The 5 greatest Boston Celtics forwards of all time
- The 5 greatest Boston Celtics guards of all time
After not winning anything for the first decade of Paul Pierce’s Celtics career, Ainge finally got Pierce the help that he needed in the summer of 2007, when he pulled off a blockbuster deal for another future Hall-of-Famer: Kevin Garnett.
Garnett proved to be exactly the big man that the Celtics needed to reach the next level. In his first season in Boston, Garnett was an All-NBA first-teamer and won the league’s Defensive Player of the Year Award. Alongside Pierce and Ray Allen, Garnett helped lead the Celtics to a dominant season and an NBA title.
After the 2008 title season, Garnett would go on to play five more seasons in Boston, making four more All-Star Games, and leading the Celtics back to the NBA Finals in 2010, as well as within one game of a third Finals trip in 2012.
Despite the fact that he only played six years in Boston, Garnett accomplished enough during that time to establish himself as an all-time Celtics great, thus rendering this as easily the best deal of Danny Ainge’s career.

