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Grade the trade: Blazers deal Lillard to Celtics in latest lose-lose proposal

Andrew Hanlon
Andrew Hanlon

Rip City Project

Damian Lillard, Portland Trail Blazers (front), Jayson Tatum, Boston Celtics (Photo by Maddie Meyer/Getty Images)

Rumors and potential trades continue to surround Damian Lillard and the Portland Trail Blazers, the latest of which has Dame heading to the Northeast.

Lillard wants to play for the Miami Heat; that has been made nauseatingly clear. But realistically, it doesn’t matter where the Trail Blazers send him. Portland General Manager Joe Cronin has publicly stated numerous times he’s going to do what’s best for the franchise, which is what he should be doing.

At this point, that means not accepting the Heat’s offer.

But what are the other options?

Blazers trade Damian Lillard to Boston Celtics for spare parts in B/R proposal

Lillard said earlier this summer that he doesn’t want to play in Boston, but is he the type of person and player to hold out if he doesn’t land at his desired destination? Despite what his agent Aaron Goodwin says, no, he’s not.

Wherever Dame ends up next season – even if that’s in Portland, at least to begin with – he’s going to put on a jersey and play.

But what could a potential Blazers-Celtics trade look like, and would this proposal be worth it for Portland? (Hint: Absolutely not.)

Robert Williams III and Malcolm Brogdon could come to the Blazers from the Celtics in a Damian Lillard trade.
Robert Williams III, Boston Celtics (left), Malcolm Brogdon (Photo by Brian Fluharty/Getty Images)

This deal is a loss for both franchises unless the wildly expensive combination of Lillard, Jayson Tatum, Jaylen Brown and Kristaps Porzingis cruise to an NBA title.

Tatum is on a five-year, $163 million contract with a player option for $37 million in 2025-26 (that he’ll surely decline to sign a new, far more lucrative deal). The Celtics just extended Porzingis for two years, $60 million. Brown is eligible for an extension that could reportedly surpass the $300 million mark.

Derrick White is on the books for about $18 and $19 million the next two seasons, respectively, and 37-year-old Al Horford is still owed $19.5 million over the next two years.

Adding Lillard and his $200 million across the next four seasons is cap and luxury tax suicide, especially with the incoming second apron as part of the new collective bargaining agreement. The Celtics better win the title this season and find a way to immediately shed salary or this team is going to continue to become really, really, really expensive.

That’s all assuming majority owner and governor Wyc Grousbeck signs off on a deal that will cost his team hundreds of millions of dollars in the first place.

Robert Williams III could be part of the Blazers return from the Celtics in a Damian Lillard trade.
Robert Williams, Boston Celtics (center) (Photo by Adam Glanzman/Getty Images)

The Trail Blazers would be trading Damian Lillard for a poo-poo platter

This isn’t a huge win from Portland’s perspective, either. Brogdon is an OK guard who would essentially take Lillard’s spot on the roster, but a major injury is always just a step away with him. Pritchard showed some promise as a reserve guard and shooter as a rookie before falling out of Boston’s rotation last year.

Hauser is inexpensive and a 6-foot-8, 250-pound floor spacer, while Kornet isn’t much more than a small expiring contract, although Portland could use some extra size, even if it’s from average to below-average players.

The attractive pieces of this return are Williams III and a few future Celtics first-round picks (perhaps). Let’s break that down:

  • Williams is one of the best defensive centers in the NBA when healthy. His athleticism and ability to play as an explosive rim-runner next to Scoot Henderson would be a boon for the Blazers’ offense – or at least it would be if he were on the floor, which he rarely is. RWIII has played 209 total games in five NBA seasons and has only played in more than 52 once.
  • A top-four protected Warriors pick next season will almost certainly end up as a late-20s selection.
  • A Celtics pick just one year later, after a season in which Boston will still have Tatum, Lillard and White – and this is assuming they get rid of Brown, somehow, to save money, which is unlikely – will also probably end up in the late 20s.
  • A 2027 Celtics first sounds a little more promising for Portland, but Lillard and Tatum, at the very least, should still be in Boston. That means another pick that likely lands in the back half of the first round.
  • A 2029 first-round selection via Boston is the most alluring from the Blazers perspective, but it’s also top-five protected, so if the Celtics really do bottom out after all this, there’s still a chance Portland doesn’t land a high draft pick.

Is this trade package from the Celtics better than what’s been rumored to be coming out of Miami? For sure. And maybe the Blazers simply can’t do much better. But a quartet of first-round picks that don’t sound promising and a center who can’t stay on the floor doesn’t do much for Portland’s future.

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.