Boston Celtics president Danny Ainge, usually known as one of the best poker-like executives in the league, made his toughest call in the offseason table of his front office career by trading fan-favorite Isaiah Thomas to the Cleveland Cavaliers in exchange for Kyrie Irving.

While concerns of hip and labrum injuries were roaming the front office, ridding the franchise of a star of Thomas' caliber proved a decision more challenging than most believe.

“It was definitely the toughest call I ever had to make,” Ainge told Gary Washburn of The Boston Globe. “It’s in everybody’s best interest that I don’t share all the reasons [for the trade]. But the bottom line is obviously I felt like it was the right thing for our franchise to do. But it’s a deep and complicated process. It’s not as simple as people think it is.”

Article Continues Below
More NBA News
Rutgers Scarlet Knights guard Ace Bailey (4) looks to pass during the second half against the Illinois Fighting Illini at Jersey Mike's Arena.
Paul George gives Ace Bailey advice on NBA Draft stock dropBenedetto Vitale ·
Miami Heat guard Davion Mitchell (45) dribbles in the first quarter against the Cleveland Cavaliers at Rocket Arena.
Heat makes Davion Mitchell contract move ahead of free agencyZachary Weinberger ·
Los Angeles Lakers forward LeBron James (23) moves to the basket against Minnesota Timberwolves forward Jaden McDaniels (3) and guard Mike Conley (10) during the second half in game five of first round for the 2025 NBA Playoffs at Crypto.com Arena.
Lakers’ LeBron James hilariously recalls ‘most egregious’ travel of his careerJackson Stone ·
Charlotte Hornets color commentator Dell Curry before the game against the Golden State Warriors at Chase Center.
Exclusive: Dell Curry reveals what’s ‘tough’ about Hornets’ draft decisionDJ Siddiqi ·
Denver Nuggets center Nikola Jokic (15) watches Oklahoma City Thunder guard Shai Gilgeous-Alexander shoot free throws in the second half of game seven of the second round for the 2025 NBA Playoffs at Paycom Center.
Nuggets’ nightmare scenario that would lead to unthinkable Nikola Jokic tradeZachary Howell ·
New Orleans Pelicans guard CJ McCollum (3) passes the ball against Washington Wizards guard Jordan Poole (13) during the second half at Smoothie King Center.
Pelicans, Wizards trade grades for Jordan Poole-CJ McCollum swapZachary Howell ·

Ainge explained his experience with being traded and also dealing with free agency, that while a lot different from this day and age, still proved quite the emotional process as a player and now an executive in the league.

“And again, being a player in professional sports for 18 years and being traded twice and signing as a free agent once and playing on championship teams and being a coach in this league and being an executive for as long as I have, I think I’ve got a pretty good grasp on all of the emotions and I have a pretty good understanding how real this all is involving players and their lives and their families and the disruptions and the emotions,” said Ainge. “I get all that and that’s not easy for players and for coaches and for executives that invest a lot into these players.”

“It’s not easy for these office people that become great friends with the players. There’s a reality that I see and that’s what makes any sort of trade challenging. But it’s just part of the world that we live in, but it’s got to be done. You’ve got to do what’s best for the franchise. The franchise is bigger than all of us. Bigger than one individual.”

Thomas was noticeably upset when he first received the call from Ainge, but as he forges his future with his new organization in the Cleveland Cavaliers, it's likely him and Ainge will be back in good term as time often heals most wounds.