The Boston Celtics reached the Eastern Conference Finals in 2017, 2018, and 2020, but last season was a massive disappointment and this season is off to a sluggish 14-14 start. There has been some buzz around the NBA about the Celtics shaking things up in a big way by trading Jaylen Brown and breaking up his All-Star pairing with Jayson Tatum, though other reporting suggests Boston doesn't really have much interest in that right now.
If the Celtics actually do decide to move on from Brown, they must make sure they get the best return for Brown because he is a phenomenal talent who's still just 25 years old. Looking at another example, the Toronto Raptors felt the core of Kyle Lowry and DeMar DeRozan was terrific, but their one major move of acquiring Kawhi Leonard for DeRozan catapulted them to the mountaintop. Thus, this may seem like a similar situation if Brad Stevens could negotiate a deal and find the perfect pieces to complement Tatum.
As Boston is an organization that is known to always compete for championships, the fan base has been eager to reach the NBA Finals again since their last appearance was in 2010. One massive move could swing the tide enormously, but it must be a calculated risk because moving Brown for just anyone could be a disaster for this era of the Celtics.
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Best Jaylen Brown trades for Boston Celtics
Acquiring Fred VanVleet and OG Anunoby for Brown would be a remarkable return because of the multitude of roles they could play for Ime Udoka. Their two-way prowess fits the style of play in this generation, and VanVleet could finally be the point guard that Boston has been seeking. Additionally, Anunoby has proven to flourish even if his usage is at a low rate.
VanVleet and Anunoby's championship experience would be a tremendous help for the Celtics franchise. The defensive versatility of VanVleet, Anunoby, Tatum, Marcus Smart, and Robert Williams III could possibly make Boston a top-three defense in the league. Moreover, VanVleet and Anunoby would boost their depth as well, which is another weakness that Boston has possessed over the last few years.
This Ben Simmons-Brown swap has been brought up in rumors, with Brown representing the kind of All-Star-level player Daryl Morey wants in a Simmons trade. However, it does not seem as if there have been any serious negotiations on this front. Still, it's a swap that would make some sense for both sides if they were to discuss it, though ESPN's Zach Lowe suggests the Philadelphia 76ers needing to include “major pieces” for a deal to work. Would Morey go for that and be willing to include somebody like Seth Curry? That feels unlikely, but never say never.
Simmons and Smart would be a headache defensively for any opponent, and the disgruntled Sixers star would bring in some much-needed playmaking juice. After the departure of Isaiah Thomas, the Celtics have not been able to find an ideal orchestrator for their offense, but Simmons would bolster their pace and help create easy baskets in transition. We'll see if either side pushes for a deal here.
This is obviously a major long shot, because Damian Lillard seems committed to Portland. Despite all the rumors, Lillard says time and time again he wants to figure things out with the one NBA team he has ever known.
However, there are still two months before the trade deadline, and perhaps the Blazers continue to struggle. They've lost seven games in a row and sit at 11-18 on the season. If things don't turn around, perhaps Dame changes his tune, and Boston would need to be ready to strike. The Celtics would need to give up quite a haul to get Lillard, but pairing Dame and Tatum would be deadly. At the very least, this is something Boston must keep an eye on.
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