Ranking 4 lucrative trade packages for Blazers to deal Scoot for a star

NEW ORLEANS, LOUISIANA - JANUARY 02: Pascal Siakam #43 of the Toronto Raptors drives against Zion Williamson #1 of the New Orleans Pelicans during the first half at the Smoothie King Center on January 02, 2021 in New Orleans, Louisiana. 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 Jonathan Bachman/Getty Images)
NEW ORLEANS, LOUISIANA - JANUARY 02: Pascal Siakam #43 of the Toronto Raptors drives against Zion Williamson #1 of the New Orleans Pelicans during the first half at the Smoothie King Center on January 02, 2021 in New Orleans, Louisiana. 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 Jonathan Bachman/Getty Images) /
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Portland Trail Blazers
Jaylen Brown, Boston Celtics and Trendon Watford, Portland Trail Blazers. Photo by Alika Jenner/Getty Images /

Trade No. 3: Celtics duck the payday as Blazers add Jaylen Brown

The Boston Celtics have an All-NBA forward in Jaylen Brown that they aren’t sure if they want to keep around. Brown is eligible for a massive supermax contract extension this summer, and if the Celtics pay Brown and then Jayson Tatum next summer, they will owe well over $100 million to just two players. In the era of the second tax apron, that’s a punitive position to be in.

After trading Marcus Smart for Kristaps Porzingis, the Celtics can give their backcourt a makeover by adding Henderson and Simons. They get out of paying Brown, can bring Henderson along behind Malcolm Brogdon and Derrick White, and suddenly have a lot more playmaking juice.

Here’s how it would look:

The Trail Blazers get the two-way wing they haven’t had since…well, maybe Nic Batum? Brandon Roy? For a team that excels at developing guards, they have been a wasteland at small forward, so adding Brown would be a godsend. The Blazers don’t need him to be an elite on-ball creator and dribbler, because they have one of the league’s best in Lillard.

This is a lot to give up for Brown; Simons is a high-scoring guard in his own right, Henderson looks like a future star, with another pick to boot. That’s why this deal isn’t higher on the list.

But Brown is a player the Blazers aren’t going to find any other way, and he’s ready to compete right now. That’s a tempting move for Portland to consider.