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Raptors' all-in risk for Kawhi Leonard proves Celtics Must Stand Firm on Jaylen Brown

If 35 year old Kawhi Leonard can fetch two future unprotected first round picks, two future second-round picks, and a first-round pick swap, Jaylen Brown's
Mar 21, 2026; Dallas, Texas, USA; LA Clippers forward Kawhi Leonard (2) runs back up court during the game between the Mavericks and the Clippers at American Airlines Center. Mandatory Credit: Jerome Miron-Imagn Images
Mar 21, 2026; Dallas, Texas, USA; LA Clippers forward Kawhi Leonard (2) runs back up court during the game between the Mavericks and the Clippers at American Airlines Center. Mandatory Credit: Jerome Miron-Imagn Images | IMAGN IMAGES via Reuters Connect

There’s no shortage of reporting on the lack of a trade market for Jaylen Brown and how the Celtics are going to have to significantly lower their demands if they actually want to make a deal. And yet, on Tuesday, the Raptors, a team that had some level of interest in Brown, traded for another star two-way wing in Kawhi Leonard.

Toronto gave up Brandon Ingram, Gradey Dick, 2 unprotected first-round picks in 2031 and 2033, 2 second-round picks in 2030 and 2033, and a first-round pick swap in 2027 to bring the 2019 Finals MVP back to the Raptors.

But that’s a pretty penny. Don’t get me wrong, Brandon Ingram is probably a neutral asset at best, and perhaps a negative with his contract, but he was an All-Star last year and has only one more year on his deal followed by a player option. Dick hasn’t had a ton of success, but he’s an interesting young player.

Raptors taking major risk with draft capital in Kawhi trade

The real prize here, though, is the picks. The two unprotected picks in the 2030s are premium assets. Kawhi is an outstanding player, and he’s coming off one of the best seasons of his career, plus he had incredible success in his one season in Toronto.

At the same time, he’s 35 years old and, going back to the 2016-17 season, he’s averaging just 44.4 regular-season games played per year. If that’s good for two firsts, two seconds, and a swap, the 29-year-old Brown should be worth considerably more. 

The Celtics are likely asking for 3-4 first-round picks and young players at the very least in any deal, and that’s reasonable. That’s what he’s worth to the Celtics, and that’s what he should be worth to a team that’s looking for a superstar to get them over the hump. As we just saw with Kawhi, you only need one team to meet your asking price, and eventually, somebody is going to cave because Brown is one of the best 10-20 players in the league, and those guys matter a lot and are hard to acquire.

Celtics need positive trade return for Brown

We know the Raptors were in on Brown. Did they offer this deal? Did they offer more picks? Who said no? Maybe they were a unique case and wanted Kawhi more because of his past history. Maybe they think Kawhi is the better player - right now, if he can stay healthy, he very well may be. Maybe they wanted the shorter-term window with a Kawhi extension versus one for Jaylen.

These are all variables that we don’t know. But it’s fascinating to see what the market is for a wing player who just came in 7th in MVP and finished second-team All-NBA, having about as comparable a season to Jaylen Brown as one possibly could. Leonard has had the better career, but again, he’s 35 and injury-prone while Brown is just entering the prime of his career.

Either way, this trade is a great reminder that these kinds of players are worth a lot in today’s NBA. While JB’s contract may be a little higher than you’d like, he’s still an incredibly valuable player, one who drives winning at a high level and has a proven track record of success in the playoffs. If the Celtics don’t find a deal that they love, they certainly don’t need to move forward.

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