Celtics SF Jaylen Brown to Trail Blazers? 2 trades to consider

the Boston Celtics They head to the couch after a heartbreaking Game 7 loss at home against Miami Heat.



The defeat comes after winning three consecutive elimination games, including a thrilling winner from Derrick White at the last whistle in game six on Saturday.

For the Celtics, Boston has now been in the Eastern Conference Finals five times in the past seven seasons but has yet to lift the Larry O’Brien Trophy. This means that the Celtics may be looking to make some changes, namely with Jaylen Brown.

Brown, 26, has one more year left on his contract, but he’s eligible for a five-year, $295 million extension from the Celtics this offseason. If Boston signs him to this deal, it pretty much locks the Celtics into that core, which was good but ultimately proved unsuccessful in winning a championship. This could mean that the Celtics decided to rearrange the deck and find a new home for Brown before he could test for free agency.

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

Portland and Boston make sense as business partners, and the deal could go either way. Ranger’s Kevin O’Connor suggests the Celtics could target point guard Damian Lillard.

“The top target on my list will be Damian Lillard, a born leader with elite shot-making skills,” O’Connor writes. “Lillard is much stronger than Brown, and he brings more attacking versatility because he’s able to thrive as an off-the-ball shooter and settle into a passing-first role when necessary.”

Lillard’s pairing with Tatum could bring the Celtics to the promised land, but due to the fact that Dame turns 33 in July, it shrinks Boston’s title window. Acquiring Lillard would give the Celtics a promotion, but it would cost Boston more than just the Browns to acquire Lillard. Expect several future draft picks and another solid player or two (Malcolm Brogdon, Derrick White, Marcus Smart?) to be essential in any trade.

According to O’Connor, there is another route the Blazers and Celtics could take in any Brown speech. In this world, the Celtics trade Brown to the Blazers, but Portland will keep Lillard, which is what the team (and the lady) ultimately want.

The Blazers are said to be reluctant to take on Lillard and might prefer to flip the number. 3 Selected in the June draft to support the team around him. While I remain skeptical that this will still be true if Lillard’s performances are strong enough, the Celtics should also consider a different basis for Portland’s trade: Brown to the Blazers for Anfernee Simons and no. 3 pick. Simmons is a lesser playmaker than Lillard, but he was a super competent 30-point-per-game scorer when he ran the show in the games Lillard has missed this season. Simmons is also more of a passer-by than Brown. Boston could also use that third pick in a separate trade or keep it to pick a young playmaker like G League’s Scoot Henderson, Elite Extra Secretary or Ausar Thompson.

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

The decision ultimately hinges on how the team feels about its current position and Tatum, arguably the top 5 player in the league. It’s understandable that the Celtics want to keep Tatum in Boston for the remainder of his career, but they could sacrifice some of his upcoming primes to preserve more long-term success. If they feel they wouldn’t sacrifice too much by grabbing a rookie and Simmons to replace Brown, it should be a deal Boston should consider.

It’s reasonable to think that the Blazers, a team looking for an “elite small forward,” would be interested in a deal like that to take on the Browns, perhaps the best player Portland could get via trade this season. Whether Brown is brought in as Lillard’s partner in crime or the player to carry the torch after him, the Blazers must listen.

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