The Celtics reportedly offered the Spurs a strong collection of draft picks for Kawhi Leonard.

But San Antonio, prioritizing winning now, wanted capable veterans. So, the Spurs sent Leonard to the Raptors for DeMar DeRozan, Jakob Poeltl and a late first-round pick – a deal that worked for both sides. San Antonio continued its playoff streak. Leonard led Toronto to the NBA Finals.

Boston, on the other hand, was left in the cold. The Celtics endured a rocky season that ended in the second round. Kyrie Irving appears likely to leave.

Chris Mannix of Sports Illustrated:

I do know that there’s some regret from some people within the Celtics organization about not pulling the trigger on a Kawhi Leonard deal last summer.

They could have made a deal for Kawhi Leonard – my understanding, from kind of both sides of this – involving Jaylen Brown and Marcus Smart. At least Jaylen Brown as the centerpiece of it all.

Smart was a free agent, so he would have had to agree to a sign-and-trade. That gets complicated. But Boston also signed him just after San Antonio the Leonard trade. So, maybe that was actually in play.

With Leonard thriving throughout the playoffs and Brown having an underwhelming year, Boston clearly missed a great opportunity. But hindsight is 20-20.

Leonard was coming off a lost year due to injury, and his health was a major question. He’ll also become an unrestricted free agent this summer, and the flight risk was real (and still is for Toronto). The possibility of losing both Leonard and Irving in one summer would have have been daunting.

Brown had just helped lead the Celtics to Game 7 of the conference finals. He appeared to be part of a promising young core with Jayson Tatum.

So, it’s easy to say now that Boston erred. Making the call this summer would have been more difficult.