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Celtics SF Jaylen Brown to Blazers? 2 Trades to Consider

The Portland Trail Blazers could be a landing spot for Jaylen Brown if the Boston Celtics look to trade him this offseason.

Portland Trail Blazers (93) Vs. Boston Celtics (115) At TD Garden Photo by Erin Clark/The Boston Globe via Getty Images

The Boston Celtics are heading to the couch after a heartbreaking Game 7 loss at home against the Miami Heat.

The defeat comes after winning three straight elimination games, including a thrilling game-winner from Derrick White at the final buzzer of Game 6 on Saturday.

For the Celtics, Boston has now been to the Eastern Conference Finals five times in the last seven seasons but have yet to hoist the Larry O’Brien Trophy. This means that the Celtics could look to make some changes, namely with Jaylen Brown.

Brown, 26, has one more year left on his contract, but is eligible for a five-year extension worth $295 million from the Celtics this offseason. Should Boston ink him to that deal, that pretty much locks the Celtics into this core, one that has been good but has ultimately proven unsuccessful at winning a championship. This could mean that the Celtics decide to re-shuffle the deck and find a new home for Brown before he can test free agency.

A team that would be interested in a player like Brown is the Portland Trail Blazers, who are looking to add some top-tier talent to the roster.

Portland and Boston make sense as trade partners, and a deal could go either way. The Ringer’s Kevin O’Connor suggests that the Celtics could target point guard Damian Lillard.

“The top target on my list would be Damian Lillard, a born leader with elite shot-creation skills,” O’Connor writes. “Lillard is far more potent than Brown, and he brings more offensive versatility since he can both thrive as an off-ball shooter and settle into a pass-first role when necessary.”

Pairing Lillard with Tatum could bring the Celtics to the promised land, but given the fact that Dame turns 33 in July, it shrinks Boston’s title window. Getting Lillard would give the Celtics an upgrade, but it is going to cost Boston more than just Brown to acquire Lillard. Expect several future draft picks and another strong role player or two (Malcolm Brogdon, Derrick White, Marcus Smart?) to be necessary in any deal.

According to O’Connor, there is another path the Blazers and Celtics could take in any Brown discourse. In this world, the Celtics trade Brown to the Blazers, but Portland gets to keep Lillard, which is what the team (and Dame) ultimately wants.

The Blazers are reportedly reluctant to deal Lillard and might prefer to flip the no. 3 pick in June’s draft to bolster the team around him. While I remain skeptical that that would remain true if the Lillard offers are strong enough, the Celtics should also consider a different foundation for a Portland trade: Brown to the Blazers for Anfernee Simons and the no. 3 pick. Simons is less of a playmaker than Lillard, but he was a super-efficient borderline-30-point-per-game scorer when he ran the show in games that Lillard missed this season. Simons is also more of a passer than Brown. Boston could also use that third pick in a separate trade or keep it to select a young playmaker such as the G League’s Scoot Henderson or Overtime Elite’s Amen or Ausar Thompson.

This deal gives the Celtics less in the short term, but potentially a stronger return in the long run.

The decision ultimately hinges on how the team feels about its current position and Tatum, arguably a top-5 player in the league. The Celtics understandably want to keep Tatum in Boston for the remainder of his career, but could sacrifice some of his upcoming prime to sustain more long-term success. If they feel like they won’t be sacrificing too much by taking on a rookie and Simons to replace Brown, then this should be a deal Boston should consider.

It’s reasonable to think that the Blazers, a team searching for “an elite small forward,” would be interested in a deal like that to take on Brown, possibly the best possible player Portland could acquire via trade this offseason. Whether Brown is brought in as Lillard’s partner-in-crime or the player to carry the torch after him, the Blazers should listen.