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The Boston Celtics Make Risky Bet

The Boston Celtics Make Risky Bet
Photo/ Winslow Townson-USA TODAY Sports

The wait is finally over for the anxious “Green Teamers” who have been wondering when a Jaylen Brown contract extension would come. On Tuesday afternoon, the All-Star wing agreed to sign a five-year $304 million max contract extension with the Boston Celtics


Getting an extension done was a listed priority by President of Basketball Operations Brad Stevens. 


“He’s a big part of us moving forward,” Stevens said at his June 1st press conference.



While it took a bit longer than expected, Stevens was true to his word at the beginning of the offseason, showing that he had a vision of where the team’s direction was well before he made the move to get Kristaps Porzingis


But surrounding the agreement, there hasn’t been a consensus on what the deal means for the Celtics long-term. More concretely, many fans wonder if the extension will follow the same path that similar deals of superstars, who are currently demanding to be traded (Lillard), might be the blueprint for their future. Will Brown ask for a trade just a few years in? Or will his financial burden hinder the team from adding depth?


Neither of those questions addresses the fact that the Celtics just retained a 26-year-old All-NBA forward who is coming off a year of career highs in scoring, rebounding, and shooting percentage. The recency bias in how Brown’s game is being evaluated has completely glossed over the caliber of player Jaylen Brown is. More than that, keeping Brown under contract allows the Celtics to stay in the mix as contenders for the NBA championship. 


Jaylen Brown’s New Contract 


Brown’s contract is the largest contract in terms of total money ever in NBA history. His contract follows the 35% cap-salary structure stipulated in max contracts starting the year his extension goes into effect (2024-2025). His salary will rise by 8% each year based on the projected salary cap number in the corresponding season. Meaning his salary will increase 32% from year one to year five. 



Brown’s commitment to staying with Boston long-term had been questioned in recent seasons. A five-year extension would normally squash that belief. Nonetheless, speculation surrounded whether Brown would get a player option included in the deal. Shams Charnia of the Athletic reported that the sides agreed not to include a player option, yet they settled on a trade kicker. A trade kicker is designed as a “bonus” for being traded. The figure is a percentage of the player’s salary (anywhere from 5%-15%) that the team trading the player has to pay. 


The debate about if Brown’s deal instantly vaults him into the “worst contract” in the league contract is too reductive—all of those who believe that are just looking at the salary number. If you put it in the context of Bradley Beal and Damian Lillard’s extensions, the situation is vastly different. 


The Boston Celtics Financial Future 


Will the Celtics have any buyer’s remorse down the line? Roster decisions likely get more challenging the deeper Brown’s contract goes. Still, the money given in the extension would be used somehow, especially since the Celtics have been players in the star player market for over a decade. 


The new CBA has strict penalties for teams exceeding the salary cap’s second apron. Those restrictions won’t factor in for about three years. However, the Celtics also have to worry about their other star player. Jayson Tatum becomes a free agent in 2026, and his contract will most likely exceed $350 million in total money by that time. Including the Porzingis cap hit, and the Celtics have about 75% of their salary cap locked up in three players in the coming years. 


Something that has been an advantage for recent Celtics teams has been depth. They ran ten-man rotations with ease last season during the regular season. But with the loss of two key depth pieces in Marcus Smart and Grant Williams, are they sacrificing too much to attain stars? 


The Deciding Factors


The Boston Celtics have made the Conference Finals in five of Brown’s seven seasons in Boston. That level of success separates them from many so-called contenders in the NBA. That being said, with Brown, the Celtics have failed to achieve the ultimate goal of winning a championship. Seven seasons is a lifetime in the modern NBA. This indicates why some were positioning Brown in trade talks these past two offseasons. 



He underperformed against the Miami Heat in the Eastern Conference Finals by any standard, including his own. He averaged 19 points, 6.1 rebounds, and 3.4 assists for the series, shooting 41% from the field and 16% beyond the arc, according to data from Basketball-Reference. More glaring was Brown’s inability to control his dribble. That snowballed into him committing 25 turnovers in seven games. But one series shouldn’t define a player. Especially a performer the caliber of Jaylen Brown. It’s bad practice to strictly discredit a player’s ability on a sample size of seven games. Go back to the previous playoff series, and Brown’s numbers were back where we expected them to be. 


Brad Stevens is taking the same approach. Trading away (or not extending) a top-20 player who is under 28 years old would be foolish. Considering the Boston Celtics now have at least a two-year window with Tatum, Porzingis, and Derrick White, keeping Brown gives them a better chance at staying in the hunt for something they have come close to achieving. 



Matt Strout is a contributor to Back Sports Page. Matt studied Journalism and Sociology at Temple University for four years and graduated in May of 2022. While there, Matt wrote for multiple student and professional publications covering sports and the City of Philadelphia. Matt is originally from Maine and now resides in California. He has written content primarily for the NBA and PGA Tour. You can catch Matt frequently as a guest on the “Cut The Nets” podcast featured on the Back Sports Page network. When Matt is not writing, he enjoys cooking and playing golf. Follow Matt’s social media on Twitter @TheRealStrout or Instagram @matt_strout96 

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