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Jaylen Brown's looming contract extension may be x-factor in potential Giannis trade

Jaylen Brown is eligible for a contract extension this summer. However, with three years left on his deal, the Celtics star may have to wait.
Oct 28, 2024; Boston, Massachusetts, USA; Boston Celtics forward Jaylen Brown (7) drives to the basket defended by Milwaukee Bucks forward Giannis Antetokounmpo (34) during the second half at TD Garden. Mandatory Credit: Paul Rutherford-Imagn Images
Oct 28, 2024; Boston, Massachusetts, USA; Boston Celtics forward Jaylen Brown (7) drives to the basket defended by Milwaukee Bucks forward Giannis Antetokounmpo (34) during the second half at TD Garden. Mandatory Credit: Paul Rutherford-Imagn Images | Paul Rutherford-Imagn Images

Jaylen Brown becomes eligible to sign a contract extension on Jul. 26. One couldn't help but wonder if that's what he was referring to when he said on his May. 6 Twitch stream, "I love Boston. And if it was up to me, I could play in Boston for the next 10 years."

The Marietta, Georgia, native is coming off a career year. He earned his first start in the All-Star Game and finished sixth in the MVP voting. He has three years left on his supermax deal. At the time, that made Brown the highest-paid player in the NBA. Of course, that's a short-lived title. The next summer, it was Jayson Tatum's turn through the revolving door to the most lucrative contract in league history.

If Brown tacks two more years onto his current pact, it will extend his deal through the 2030-31 campaign. That would take him through his age-34 season.

Based on current cap projections, the Boston Celtics would be agreeing to give him $66.85 million, [35 percent of the salary cap], in 2029-30. He would then make $72.2 million, [36 percent of the salary cap], the following year. That's adding a total of $139 million to the $183 left on his contract.

Would Brown rock the boat without an extension this summer?

Players with three years left on their deal typically don't receive max extensions. The former Finals MVP can point to Devin Booker as a recent exception. The Phoenix Suns went against the grain last July when they gave the face of their franchise a two-year extension, taking him from $145 million over three years to $316 million over five.

That move with Booker, who was 28 at the time, didn't exactly receive rave reviews. And it's probably not a deal that will persuade the Celtics to act now.

Really, the only reason they would do so is if they ultimately decide it's best to keep one of their franchise cornerstones happy. However, it seems unlikely that Brown would demand a trade or create headaches for the organization if they don't budge. He'd love the peace of mind from getting this done now, not having to worry about something like an injury potentially hurting his next payday. Understanding the circumstances, it's probably a decision he can accept, though.

If Boston doesn't believe that extension is good business, whether handing it out now or closer to the end of the five-time All-Star's contract, that would lend credence to the idea of trading for Giannis Antetokounmpo.

Then, they only have to assess three-year windows when projecting their best path forward. There's proof of concept with Brown and Tatum. There's also less concern about durability and getting an honest chance at a championship in each season while they're together.

Antetokounmpo turns 32 in December. As a two-time league MVP, he could help guide the Celtics back to the NBA summit. However, it's also a gamble that could blow up in their faces before he and Tatum share the floor on a playoff stage.

If that volatility steers them away from breaking up their star tandem, the longer Brown's in Boston, the more likely the franchise will eventually give him that extension.

While it's a matter that could be a significant factor in how the Celtics size up a potential trade for Antetokounmpo, if anything, there might be a greater likelihood that getting an extension done is a matter of when, not if. In that case, a summer blockbuster with the Milwaukee Bucks likely isn't on Boston's horizon.

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