Grade the Trade: Celtics land Lillard but keep Jaylen in new proposal

BOSTON, MASSACHUSETTS - MARCH 08: Damian Lillard #0 of the Portland Trail Blazers looks on with Jayson Tatum #0 of the Boston Celtics at TD Garden on March 08, 2023 in Boston, Massachusetts. The Celtics defeat the Trail Blazers 115-93. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Maddie Meyer/Getty Images) /

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The Boston Celtics are not afraid to take big swings. Trading a franchise stalwart in Marcus Smart for Kristaps Porzingis is certainly not a half-measure. They are banking on Derrick White stepping up and Porzingis staying healthy; it’s risky, but if it works the Celtics will be a better team.

All-NBA wing Jaylen Brown is now eligible for a supermax contract extension, but there has been no news yet of Brown agreeing to such a deal. That has led to speculation that the Celtics are considering moving on from Brown, whether they are loath to offer the extension or he is loath to sign it. They let Grant Williams go in restricted free agency rather than pay him and push their salary over the second tax apron.

Are the Celtics preparing for a big move?

What if the reason the Celtics are being careful with their money is that they have their sights set on a bigger prize than Grant Williams? Damian Lillard has requested a trade out of Portland, is great friends with Jayson Tatum, and would fill an area of need that the Celtics still haven’t addressed this summer, namely ball-handling and playmaking.

The easy path to a Damian Lillard trade would be to move Jaylen Brown to Portland, but there is a brief window to another path. What if the Celtics could add Lillard to a lineup that includes Derrick White, Jayson Tatum, Brown, and Kristaps Porzingis? Let’s see what such a trade could look like.