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Surprising Candidates For Celtics’ Most Regrettable Contract

Boston Celtics president Brad Stevens

The Boston Celtics’ championship victory in 2024 silenced any doubts about their decision to extend Jayson Tatum and Jaylen Brown with supermax contracts. Both players were integral to the team’s success, leading the Celtics to their first title since 2008. Their upcoming respective salaries of $34.8 million for Tatum and $49.2 million for Brown are a testament to the Celtics’ faith in their abilities.

Surprising Candidates For Celtics’ Most Regrettable Contract

However, these extensions raise questions about future financial flexibility. Tatum’s six-year, $348.8 million deal (with a player option) and Brown’s five-year, $285.4 million deal place enormous pressure on Boston’s payroll. Despite these contracts being deserved, the long-term cost could eventually present challenges.

Boston chose to secure its core for the foreseeable future. By paying Tatum and Brown the highest possible salaries, the Celtics made a clear statement: their championship window is now, and the future can wait. This aggressive approach has yielded success, as Boston is well-positioned for another title run in 2025. The team’s immediate prospects are bright, making regret seem unlikely in the short term.

Yet, there remains a potential downside to the Jayson Tatum and Jaylen Brown contracts. With the NBA’s new Collective Bargaining Agreement (CBA) tightening salary cap rules, keeping both Tatum and Brown may become financially burdensome. The punitive luxury tax measures are designed to discourage teams from exceeding the cap. This will force Boston into difficult decisions. In the coming years, the Celtics might have to weigh the cost of keeping both stars against the benefit of maintaining a competitive roster.

The main concern isn’t their performance. Both Tatum and Brown are elite talents, and their games should age well. The real issue lies in the financial restrictions the Celtics may face. Should injuries or declining performance arise, Boston would be locked into two massive contracts, limiting flexibility. Even though Tatum and Brown are cornerstones of the franchise, tying up over 60 percent of the salary cap in two players can have long-term consequences.

Unlikely To Be Regretted

Eric Pincus of Bleacher Report ranked the Celtics’ potential regret level for these deals at just 2 out of 10. This reflects the team’s current success and dominance. A back-to-back championship is within reach, further justifying the Jayson Tatum and Jaylen Brown contract investments. However, the reality is that this era of Celtics basketball may not last forever. The new CBA’s harsher penalties for teams exceeding the salary cap could eventually force Boston to reconsider its financial strategy.

The Celtics have the option to move one of their stars if the financial burden becomes too heavy. While it would be painful to trade either Tatum or Brown, it might be necessary to keep the team competitive in the long term. The regret, if we will call it that, would not come from paying these players their worth. It’s will be the inevitable decision to part ways with one of them to sustain roster depth and flexibility.

The Last Word

Ultimately, the Celtics’ current position as champions and contenders for another title overshadows any future concerns. The regret level is minimal. Still, the team will eventually have to face the reality that both Tatum and Brown might not retire as Celtics. This outcome is not ideal. However, it’s a manageable consequence of the franchise’s commitment to success now. In the end, the only regret Boston might face is having to break up this star tandem down the line due to the Jayson Tatum and Jaylen Brown contracts.

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