Celtics analyst ponders price for Jaylen Brown in a Trail Blazers trade offer

The Ringer's Bill Simmons openly pondered what the price would be for Jaylen Brown in a trade between the Boston Celtics and Portland Trail Blazers Mandatory Credit: Soobum Im-USA TODAY Sports
The Ringer's Bill Simmons openly pondered what the price would be for Jaylen Brown in a trade between the Boston Celtics and Portland Trail Blazers Mandatory Credit: Soobum Im-USA TODAY Sports /
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The narrative surrounding the Boston Celtics has shifted following shocking Eastern Conference Finals failures from the odds-on title favorite prior to the start of the 2023 postseason — focusing fully on what the next steps for the franchise are after looking nothing like a contender throughout the entire playoffs.

The Ringer’s Bill Simmons, a notorious Boston Celtics fan, openly wondered what the price for Jaylen Brown is this postseason, specifically honing in on what the Trail Blazers would be willing to part with in order to land No. 7 and pair the forward with Damian Lillard.

“If they do decide to do a tweak, isn’t Portland the logical destination,” Simmons said on the Bill Simmons podcast. “Portland is on a timetable with Dame, they got the number three pick in the draft. They’ve been open about saying we want to get a wing. And it just seems like that’s kind of a fit, if you’re the Celtics. Let’s say it’s number three and it’s Simons and it’s a future first and it’s a swap, or maybe it’s just number three and (Anfernee) Simons, I don’t know what Brown’s value is.”

Jaylen Brown trade could be win-win scenario for Trail Blazers and Boston Celtics

It’s not known what the perfect next step is for the Boston Celtics franchise. Handing Brown a massive payday could be the commitment the player needs to know the franchise is fully investing in him moving forward, but too much damage may have been done following the Ime Udoka situation — Brown was known to be a big fan of Udoka — and the Kevin Durant trade rumors involving Brown that consumed the summer of 2022 and briefly re-appeared at the 2023 trade deadline. Perhaps moving Brown is what the team needs to do to get the locker room on the same page again.

If they do, Portland should be a team that views itself as being just a Brown away from contention, which means a maximum trade return is possible. The Houdini believes Anfernee Simons and Shaedon Sharpe should be a minimum requirement regarding players who’d be included in a trade return, and the No. 3 pick would be best served alongside at least two other first-round draft picks.

That’d be a massive return for the Cs that keeps them flexible in upgrading the roster for next season, and Brown would join Lillard, Jusuf Nurkic, Nassir Little, and a freshly re-signed Jerami Grant in a menacing Trail Blazers core.

Brown staying in Boston long-term is the best outcome, but if he doesn’t want that, this would be a win-win scenario for both teams.