Would Celtics Trade Jaylen Brown for Kawhi Leonard and No. 5 Pick?

The Los Angeles Clippers celebrated today as the draft pick they received from the Indiana Pacers fully transformed into the No. 5 pick in the upcoming NBA Draft, as it was only protected within the top four.

It’s a huge boon for the Clippers, who don’t have their current first-rounder or much in the future, having traded most of their draft capital to the Oklahoma City Thunder in a trade that still haunts the franchise years later.

But could the Clippers flip that fifth pick for a player that can help them win now?

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While Los Angeles could keep the fifth pick and try to build a future around, most likely, an elite guard prospect alongside Darius Garland, they are in a win-now mindset, as they don’t fully control their next first-round pick until 2030.

With the Boston Celtics reportedly mulling over whether they’d be willing to take calls on Jaylen Brown this summer, could (and would) the Clippers possibly pull a trade off to give themselves a semblance of a core to build around the next few years?

L.A. could swap Kawhi Leonard on the last year of his deal over to the Celtics for the five years younger Brown, with Boston receiving the No. 5 overall pick in the process.

For Boston, they can win short-term by trying to get the most out of the two-time NBA Finals MVP alongside Jayson Tatum. Even if it doesn’t result in a title, they’d have cap space open in what could be a huge 2028 offseason, with the likes of Nikola Jokic and Giannis Antetokounmpo as free agents.

Plus, they could use the fifth pick to either bolster their roster with a player like Yaxel Lendeborg for the present or grab a blue-chip point guard like Kingston Flemings from Houston, who could be a centerpiece of your franchise for the next two decades.

Although risky for both franchises, the deal could make sense depending on how they view their near futures and the roads leading into the 2030s.

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This story was originally published May 10, 2026 at 8:27 PM.