Revisiting the Celtics’ decision to pass on Kawhi Leonard

(Vaughn Ridley/Getty Images)

After Kawhi Leonard capped a sensational series against the 76ers with a buzzer beater on Sunday, it’s easy now to forget about the question marks surrounding the All-Star last summer. The 27-year-old was coming off a year in which he played just nine games due to a mysterious quad injury and distanced himself from one of the winningest franchises and coaches in NBA history in the process. He was labeled a quitter and a flight risk for any team acquiring him with one year remaining on his deal, opening the door for the Raptors to acquire him in July for a flawed All-Star (DeMar DeRozan), a young center (Jakob Poeltl) and a protected first round pick.

The Raptors officially won that trade with San Antonio on Sunday night after Leonard’s 41-point performance clinched a spot for Toronto in the Eastern Conference Finals. Whether or not Leonard stays in Canada beyond this season remains to be seen, but the Raptors have now hit a level of success where the results justify the cost. Additionally, rumors of Leonard considering staying put up north beyond this season are picking up steam. With no hope of landing any future star in free agency (due to a cap crunch and their geography), the Raptors made an easy bet to see how far Leonard could take them after a change of personnel was needed following an ugly sweep to the Cavs in 2018.

That’s the backdrop in place as the autopsy begins on what was a disastrous 2018-19 Celtics season. While assessing what went wrong this year, it’s worth looking at the paths the Celtics declined to take from the start, and that includes failing to trade for Leonard. Playing the ‘what if?” game with trades can be a dangerous road, but no one can question the fact that the Celtics had the assets to top the Raptors offer.  

Let’s make no mistake about where the Celtics front office stood on Leonard. While they did not get the deal done, they clearly made several attempts to acquire the All-Star forward, including offering several top-tier draft picks as reported by Zach Lowe of ESPN.com last July. However, the most noteworthy part of those negotiations from Boston’s perspective were the pieces they were not willing to put on the table, and that included Jaylen Brown and Jayson Tatum according to league sources. A reminder of what was on the table from the Celtics perspective, along with some analysis of the situation from last July:

It’s starting to come into focus what exactly the Celtics put on the table for Leonard before he was dealt to the conference rival. Zach Lowe of ESPN passed this tidbit along on his Lowe Post podcast this week:

As all the reporting from this sort of trickled in, I think the Celtics offered most of their best draft picks. I don’t think the Celtics just offered, “You could have a bunch of our picks.” I think some of the picks they own – at least two of the picks, if not all of them – that they own from other teams, including the Kings, Grizzlies and Clippers, I think those were all in the deal.

So what can we piece together about the complete potential package the Spurs turned down from Boston before going with the offer of DeMar DeRozan, Jakob Poeltl and a 2019 protected first round pick?

With the confirmation from league sources that Jaylen Brown and Jayson Tatum weren’t on the table from Boston’s perspective, that leaves the Celtics with a finite number of options to make the math work. A combination of Terry Rozier, Marcus Morris, Guerschon Yabusele and Robert Williams (who couldn’t be dealt until August after he signed his rookie deal) would have served as a starting point. From there, a sign-and-trade could have been negotiated with one of Boston’s former free agents (Greg Monroe, Shane Larkin, Jabari Bird) to reach the salary threshold (at least $3 million more if Leonard waived his trade kicker) needed for the C’s to absorb Leonard’s contract. The inclusion of Marcus Smart in this type of offer seems unlikely given the fact that Rozier would need to be on the table. Boston would have wanted to retain one of those pieces for guard depth.

The rationale for the C’s refusal to discuss Brown was understandable at the time. Leonard was an injury-risk and a flight-risk with question marks about his personality in the wake of an ugly divorce from San Antonio. Brown was fresh off a breakout postseason performance in year two of his career at age 21. With Brown on his rookie deal for the next two seasons, the C’s had a potential star in the making at a bargain basement price. Giving that up for a guy who was only guaranteed to stick around for one season was tough for the front office to swallow.

There are few guys in the NBA that are worth giving up that kind of talent for, but on Sunday Leonard reminded the world that he is one of them. The small forward has been one of the best players in the planet during this postseason, carrying the Raptors on his back to the Conference Finals after averaging 34.7 points per game on 54 percent shooting in Round 2. That type of efficiency combined with his all-world defense was a throwback to the best days in San Antonio and should allow the Raptors to give the Bucks a true fight in the next two weeks.

It’s evident now that the Celtics front office was in a situation last offseason where