With Jaylen Brown signed, Celtics wont have to worry now but maybe later

The Boston Celtics finished their biggest remaining piece of business by agreeing with Jaylen Brown on a five-year, $304 million contract extension on Tuesday that will take over temporarily as the biggest contract in NBA history.

The Boston Celtics finished their biggest remaining piece of business by agreeing with Jaylen Brown on a five-year, $304 million contract extension on Tuesday that will take over temporarily as the biggest contract in NBA history.

As The Athletic’s Shams Charania first reported, Brown’s extension is fully guaranteed. Assuming the salary cap rises by the maximum of 10 percent before the 2024-25 season, the annual breakdown of the new contract will be as follows:

2024-25: $52.4 million
2025-26: $56.6 million
2026-27: $60.8 million
2027-28: $64.9 million
2028-29: $69.1 million

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The two sides took weeks to negotiate the extension, suggesting they were haggling over some of the details. The Celtics were able to avoid giving Brown a player option in the final year of the deal, while he was able to secure a trade kicker that will increase the value of his contract if Boston eventually moves him. Brown became eligible for the five-year supermax extension by making second-team All-NBA last season.

BREAKING: Boston Celtics star Jaylen Brown has agreed to a five-year, $304 million supermax contract extension with the franchise, per sources. This is the richest deal in NBA history, negotiated by agent Jason Glushon.

Fully guaranteed, with a trade kicker. No player option. pic.twitter.com/MQ6NKILY8Q

— Shams Charania (@ShamsCharania) July 25, 2023

Despite any outside speculation that popped up because the extension didn’t materialize shortly after Brown became eligible on July 1, president of basketball operations Brad Stevens never hid his desire to keep the All-NBA forward in Boston for years to come. After the playoff exit, Stevens said he believed in Brown and was “thankful for him.” With Boston coming off a disappointing Eastern Conference finals loss to Miami, Stevens used that situation to highlight Brown’s unwavering dedication to improvement. At the time, Stevens made it clear he saw Brown in the team’s plans.

“I’m really thankful for when those guys have success, they come back to work,” Stevens said. “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. It’s kind of like what I talked about with leadership earlier. Those qualities, they aren’t for everybody. Jaylen had a great year, an All-NBA year. He’s a big part of us moving forward in our eyes.”

The extension solidifies that the Celtics will be building around Brown, Jayson Tatum and Kristaps Porziņģis, who are all between 25 and 27 years old. Boston will not be able to trade Brown for one year after he signs the new deal. Though Stevens has said he would still like to acquire more depth, including on the wing, it’s likely the Celtics are done with big roster moves now.

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They are hopeful the acquisition of Porziņģis will give them more ways to attack certain defensive coverages that have given them trouble in recent seasons. It remains to be seen how well the 7-foot-3 big man will fit and how much the Celtics will miss Marcus Smart and Grant Williams, but Boston should be able to put plenty of rim protection and outside shooting on the floor most of the time.

Whenever Tatum and Brown are on the court, the Celtics also will have plenty of versatility on both ends. Since Stevens took over as an executive, the team has forged an identity around the strengths of the two All-Stars.

That path has led to deep playoff runs, but no championship yet. If there’s a downside to Brown’s extension, it’s that the Celtics now have huge future money tied up in a core that has not proven it can win a title. Boston is now committed to paying Brown, Tatum and Porziņģis a combined $116.5 million during the 2024-25 season. Including the salaries of Derrick White, Al Horford, Robert Williams III, Malcolm Brogdon and Sam Hauser, the Celtics already have more than $180 million on their books for that campaign.

The league’s second apron will become a major issue then even if the team’s owners are willing to pay a big luxury tax bill. It doesn’t take a salary cap genius to figure out that the front office will eventually run into issues maintaining such a deep roster.

Tatum’s possible contract extension would kick in during the 2025-26 season, leaving the Celtics with more than $140 million tied up in their three highest-paid players. They already ran into the challenges of the new CBA during Williams’ restricted free agency this summer. The choice not to match his offer sheet from the Mavericks allowed Boston to stay under the restrictive second apron but left coach Joe Mazzulla’s second unit with one fewer proven option.

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Tatum and Brown have established they can position the Celtics as legitimate title contenders with a great supporting cast, but how would they fare without one? For teams, supermax extensions can go wrong, especially when they’re handed out to players like Brown who aren’t likely to be MVP candidates. Even last season, when he made second-team All-NBA, some advanced metrics ranked him outside of the top 25 in overall impact. Those shouldn’t be looked upon as gospel, but are an indicator Brown falls outside of the truly elite class.

Turnovers have been a playoff habit, but winning has been too. Brown is a highly productive scorer and capable defender. With the notable exception of the most recent Miami series, his usual efficiency level has normally translated from the regular season to the playoffs. At age 26, he should theoretically still be on the rise.

The Celtics will enter the season as one of the favorites to win a championship. They will need to make financial decisions down the road but also have enough draft capital to target another difference-maker via trade one day. They already have one of the league’s best teams and many of their best players are still in their 20s. Now, they have Brown signed throughout what should be his prime years.

(Photo of Brown: Mike Ehrmann / Getty Images)

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