Celtics Trades to Consider After 1st Wave of NBA Free Agency

The Boston Celtics have reached the conference finals three times in the past four NBA seasons.

They have yet to win a title during this stretch and only once advanced to the championship round.

It is, objectively speaking, a successful run, but their inability to clear that final hurdle is seemingly wearing on them. At least, that's the best explanation for what they've already done this offseason (subtracting Marcus Smart and Grant Williams and adding (plus extending) Kristaps Porziņģis) and what they might still do this roster.

Speaking of which, we're firing up the trade machine to uncover three significant swaps that might be worth pursuing.

Flipping Brogdon for Depth and Draft Picks

Megan Briggs/Getty Images

MIAMI, FLORIDA - MAY 23: Malcolm Brogdon #13 of the Boston Celtics controls the ball ahead of Duncan Robinson #55 of the Miami Heat during the first quarter in game four of the Eastern Conference Finals at Kaseya Center on May 23, 2023 in Miami, Florida. 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 Megan Briggs/Getty Images)

The Trade: Malcolm Brogdon to the Los Angeles Clippers for Nicolas Batum, Robert Covington, a 2024 second-round pick (via TOR) and a 2027 second-round pick (via MEM)

Before Boston parted with Smart, it first brokered a deal to get Porziņģis by giving up Brogdon and sending him to the Clippers. That deal fell apart due to lingering injury concerns with Brogdon, but it didn't entirely scare off L.A.

"Los Angeles even re-engaged Boston about acquiring Brogdon in recent days," Yahoo Sports' Jake Fischer reported shortly thereafter.

The Clippers seemingly covet an upgrade at point guard—they've also been linked to James Harden—and a healthy Brogdon could do the trick. He offers a wealth of experience and the ability to impact the game on or off the ball, making him a snug on-paper fit with Kawhi Leonard and Paul George.

The Celtics, meanwhile, might want more reliability than Brogdon can offer (he's only played 70 games once) or could think they have enough backcourt depth to get by without him. if they're willing to let him go, flipping him for wing depth and draft picks could make sense. Batum checks a ton of boxes as a Swiss Army knife, and Covington pairs disruptive defense with a fiery three-ball.

A Dame Mega-Deal, Part I

Sam Forencich/NBAE via Getty Images

PORTLAND, OR - MARCH 17: Damian Lillard #0 of the Portland Trail Blazers and Jayson Tatum #0 of the Boston Celtics looks on during the game on March 17, 2023 at the Moda Center Arena in Portland, Oregon. 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. Mandatory Copyright Notice: Copyright 2023 NBAE (Photo by Sam Forencich/NBAE via Getty Images)

The Trade: Kristaps Porziņģis, Robert Williams III, Malcolm Brogdon, Payton Pritchard, Jordan Walsh and three first-round picks to the Portland Trail Blazers for Damian Lillard and Jusuf Nurkić

This trade might have too many moving parts to work in reality, but the idea is that Boston potentially has a path to Lillard that doesn't involve breaking up the Jayson Tatum-Jaylen Brown tandem.

Of course, it would require giving up just about everything else the Celtics have.

And guess what? It might still be worth it, because Lillard is such an elite player, and Boston would arguably have the league's top tandem by bringing him onboard. He might not be keen on the Celtics—or any team that isn't the Miami Heat—now, but he could come around to the idea of chasing championships with two of the league's top wings.

Boston would be top-heavy after this trade and incredibly expensive, but for the reward of a potential title, it could justify the risk. Portland could ask for essentially anything from Boston, but getting two prospects (Pritchard and Walsh), three picks (plus swaps if needed) and a possible keeper at center (Williams) could help put a new foundation in place. The Blazers could also re-enter the trade market to find additional assets for Porziņģis and Brogdon.

A Dame Mega-Deal, Part II

Brian Babineau/NBAE via Getty Images

BOSTON, MA - MARCH 8: Damian Lillard #0 of the Portland Trail Blazers dribbles the ball during the game against the Boston Celtics on March 8, 2023 at the TD Garden in Boston, Massachusetts. 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. Mandatory Copyright Notice: Copyright 2023 NBAE (Photo by Brian Babineau/NBAE via Getty Images)

The Trade: Jaylen Brown, Al Horford and Payton Pritchard to the Portland Trail Blazers for Damian Lillard

If the Celtics are able to land Lillard, their cleanest path to the prolific point guard would be giving up Brown.

That's admittedly a huge price to pay—and Boston would need to send out additional players to make the money work—but so is Brown's potential supermax extension. Maybe the Celtics aren't convinced he's worth nearly $300 million. Maybe they think Lillard's skill set pairs better with Tatum's.

Either way, a Brown (plus filler) for Lillard trade doesn't feel impossible. Improbable, sure, but that's different.

With Tatum and Lillard, the Celtics could have a scoring duo that would rival anyone's, plus a deep supporting cast around them. The Blazers, meanwhile, could view Brown as their next cornerstone player or flip him (and Horford) to a third team for a horde of future-focused assets.