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Boston Celtics Between a Rock and a Hard Place

No NBA team has won more championships than the Boston Celtics, a team that rarely misses the playoffs and has often ranked among the league’s elite. Dynastic players like Bill Russell, Tommy Heinsohn, Larry Bird, Paul Pierce and Kevin Garnett have their numbers hanging from the rafters of the TD Garden as testimony to their team’s historic greatness. The current edition of the Celtics has been to at least the Eastern Conference Finals five times over the past seven seasons and the NBA Finals once, but so far Jayson Tatum and Jaylen Brown have failed to claim trophy number 18.’s Noa Dalzell offers up some cautious optimism going into the 2023-24 season.

Much has been made of the duo’s similar offensive skill set and lack of complementary skills, but at the same time, this is a core that was minutes away from taking a 3-1 lead in the 2022 Finals and a sprained ankle away from another NBA finals appearance last year. Tatum and Brown are 25 and 26 years old, respectively, and their potential can’t be capped at this point. 

The Celtics caused a stir over the summer by inking Brown to a history-making five-year, $304 million supermax extension. That seems like a lot for a player with no rings and who may not even be the best player on his team, but the Celtics had little choice. They either had to offer the extension or face the prospect that Brown could seek greener (cough, cough) pastures next summer. Once again, Noa Dalzell offers her perspective to the discussion.

This one was expected, much to the dismay of naysayers who have shouted ‘Jaylen Brown can’t go left’ all summer. The Celtics couldn’t have reasonably taken the risk of having Brown walk for nothing next year, nor was his trade value particularly high with only one year left on his current contract. While the ‘richest contract  in league history’ label may be hard to shake, at one point, Mike Conley was the owner of the NBA’s largest contract. Soon, a new crop of contracts will be signed, and Brown’s will no longer be so outstanding. The important thing is that Tatum and Brown remain bought into playing together, and as long as the Celtics have this dynamic duo, they are championship contenders.

At this point it’s probably useful to think of NBA contracts as monopoly money. Don’t get caught up breaking down how many homeless people could be fed and housed with $304 million, how many student loans could be paid off or how many state-of-the art schools could be built. Think of it as the cost of doing business in a league of millionaires run by billionaires. If you want to compete for a championship, it’s going to be expensive.

The real question now is whether or not the Tatum/Brown duo really is capable of winning a championship together. The Celtics’ historic investment in Brown puts a great deal of pressure on the squad to win now, especially with the addition of Kristaps Porzingis. On paper, the new trio has a great balance of front court firepower and back court lethality, but we’ve seen this paper before. The New York Knicks and Dallas Mavericks also saw Porzingis’ skill set as potential championship material. The reason he didn’t help the cause in either place was due largely to the plague of the big man; he simply can’t stay healthy long enough to get it done.

None of this addresses the real elephant in the locker room. Namely, neither Brown nor Tatum has shown the ability to deliver when the stakes are highest. Losing in the Finals could have been that defining moment for Tatum, who has the annoying tendency of disappearing when his team needs him most. Brown appears to be the ideal set-up man, but he’s not Batman, he’s Robin. He’s Scottie Pippen, not Michael Jordan. He’s Rajon Rondo, not Paul Pierce. To date, Tatum has not proven that he’s Batman consistently, either.

There’s no question that Boston had to extend Jaylen Brown; the price tag was somewhat secondary in their consideration. Ideally, the new contract will bring fresh motivation to his game and perhaps he has another level to reach and that might be enough to propel the Celtics to the championship. After eight years in the league, however, that seems like a stretch. As things stand right now, Tatum and Brown are just the next in a long series of NBA duos who didn’t quite have the right DNA to win the last game of the NBA Finals. That is, of course, a difficult truth to accept.


In her new article, CelticBlogs’s Noa Dalzell asks if adding three-time champion Sam Cassell as the Boston Celtics’ lead assistant coach might be the move that instills a championship mentality in their squad. There is an argument to be made that without a player with championship experience in the mix the team will perpetually fall short. Check it out here!

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Bill Ingram is Executive Editor for The Hardwood Huddle, a new website coming to soon from the creators of Back Sports Page. He has been covering the NBA for more than 20 years.


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