Celtics Trade Idea Swaps Jaylen Brown for New Guard & Top-3 Draft Pick

Jaylen Brown, Boston Celtics

Getty Jaylen Brown of the Boston Celtics reacts against the Miami Heat.

Since being eliminated by the Miami Heat in Game 7 of the Eastern Conference Finals, the rumor mill has been churning regarding the future of Boston Celtics star, Jaylen Brown. After putting forth an electric All-NBA season, the wing is now eligible for a massive   $295 million supermax extension which, if agreed upon, could cause financial pandemonium.

To some, the idea is simple — give the man his money. However, considering the fact that signing Brown to such a number would tie up roughly $600 million between him and Jayson Tatum alone, there’s an argument to be made that trading the two-time All-Star could be in the team’s best interest in the long run.

Though the front office still has some time to make a definitive judgment call on this particular situation, should Brad Stevens and company look to embark on the aforementioned latter route, Greg Swartz of Bleacher Report believes they should look to strike one particular trade with the Portland Trail Blazers.

The proposed transaction reads as follows:

Boston Celtics receive: Anfrenee Simons, Nassir Little, 2023 first-round pick (No. 3 overall)

Portland Trail Blazers receive: Jaylen Brown

Swartz would go on to explain that the haul the Celtics would be receiving in this specific scenario could keep them in a win-now mode, all while allowing them the flexibility to make even more trades should they opt to shop the top-three draft pick.

“Simons becomes an immediate starter in Boston after averaging 21.1 points per game this season, taking over Brown’s sidekick role. Little can defend multiple positions and the Celtics can shop the No. 3 overall pick in the draft for some win-now help alongside Jayson Tatum, Simons, Marcus Smart, Derrick White, Malcolm Brogdon, Al Horford, Robert Williams III and others,” Swartz wrote.

Swartz would continue on to note that the deal could wind up working out for both organizations, as the Trail Blazers, obviously, would be receiving the biggest name in the deal in Jaylen Brown who, in his eyes, “is the perfect addition to this roster, able to be a secondary scoring option to Damian Lillard while playing strong defense on the wing.”

What’s worth noting is that Brown has has been rumored to be a name on Lillard’s “list” of players he’d like to possibly team up with.

Stephen A. Smith Suggests Jaylen Brown-Damian Lillard Swap

Swartz is certainly not the only individual to suggest the idea that the Boston Celtics should consider pursuing a deal with the Portland Trail Blazers should they come to unfortunate hypothetical scenario of shopping Jaylen Brown.

Just recently, ESPN’s Stephen A. Smith mentioned the idea that if the wing threatens to demand a trade should the C’s stand strong on not extending him to a $295 million deal, they should look to Rip City to potentially take on his services.

However, unlike the proposal mentioned earlier, Smith suggests that Boston should look to bring back perenial All-Star guard Damian Lillard in return.

“There’s a guy by the name of Damian Lillard in Portland, I wouldn’t mind getting someone like him who’s a closer by the way, who’s a point guard as a closer, who’s a sniper. We got all of that stuff going for ourselves if you’re Damian Lillard. Obviously, he’s older than Jaylen Brown but [for] Jaylen Brown I think the real challenge is that he has aspirations to be that number one guy and that is never going to happen with Jayson Tatum… If he feels adamant that [he can’t serve as a 1A next to Tatum] and he needs to move on then you need to think about an abundance of parts that you can get potentially for Jaylen Brown because he is a star in this league and he is young. Either you get an abundance of players, which I don’t think is necessary, or you get a superstar-caliber sniper like Damian Lillard to come to Boston in return for his services If I’m the Boston Celtics, I’m looking at something along those lines,” Stephen A. Smith said.

Such a trade would see the Celtics create a new top-flight dynamic duo consisting of Jayson Tatum and Lillard and, as highlighted by Smith, would see the franchise save themselves from shelling out an annual salary of $59 million a year to Brown, which is more than what the seven-time All-Star Lillard (average salary of $44 million) is making.

Brad Stevens Issues Statement on Jaylen Brown

Though speculation and rumors about Jaylen Brown’s future are destined to continue on until he ultimately puts pen to paper on a new contract, president of basketball operations Brad Stevens discussed the Celtics star’s future during his end of season interviews held Thursday afternoon, and noted that he, along with his brass, hopes to see the 26-year-old stick around.

“I’ve had nothing but great conversations with Jaylen,” Stevens said. “Without a doubt, we want Jaylen to be here, and he’s a big part of us. We believe in him, and I’m thankful for him. And I said this earlier, I’m really thankful when those guys have success, they come back to work, and when they get beat, they own it, and they come back to work. So, I know that’s what they’re about. And that’s hard to find…Jaylen had a great All-NBA year. He’s a big part of us moving forward in our eyes.”

Despite his underwhelming production for the Celtics during their season-ending Game 7 of the Eastern Conference Finals, Jaylen Brown is coming off of arguably the best season of his seven-year NBA career.

Through 67 games played, the two-time All-Star finished off the 2022-23 campaign with stellar averages of 26.6 points, 6.9 rebounds, and 3.5 rebounds while shooting 49.1% from the field.

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