Are the Celtics good at spending money? Looking back at 3 of Boston's biggest contracts

The Boston Celtics just made Jaylen Brown the highest-paid NBA player ever on a single contract, giving him $304 million over five years on an extension. The deal has received mixed reactions from fans on social media debating whether or not Brown deserves such a big payday.

Some argue that such a young player with such a bright future needed to be locked down by any means necessary. Others have pointed to his lackluster performance in the most recent playoffs (especially his tendency to turn the ball over), as reason to not have given Brown the cash.

With this massive contract becoming a divisive issue among Celtics fans, let's look back at other times in recent history when Boston inked players on huge deals. Perhaps the team’s track record will justify Brown’s extension, or prove that the Celtics aren’t so good at spending money after all.

#1, Jayson Tatum

Boston gave Jayson Tatum a five-year, $163 million rookie extension before the 2020-21 season, and it looks like there won’t be much regret looking back on this deal. Tatum has proven to be a top talent in the league that can carry a franchise on his back, and has many years of dominant play ahead of him.

Now that Brown (the Robin to Tatum’s Batman) will soon be earning an average of about $61 million per year, Tatum’s contract looks like an absolute steal at just $32.6 million. Not much has to be said about this move; it was a no-brainer for Boston.

Boston Celtics forward Jayson Tatum

#2, Kemba Walker

Walker’s contract is one of the few in recent years that Boston probably wishes they could have back. As part of a sign-and-trade that sent Terry Rozier to the Charlotte Hornets, Walker came to the Celtics in 2019 on a four-year, $140 million maximum contract.

Walker was dealt a subpar hand during his time in Boston, having to deal with injuries and the COVID-19 pandemic in his two-year stint. He was able to be a part of a deep playoff run in the 2020 bubble, but after a disappointing first-round exit the next year, his time with the team was up.

Walker was traded to the Oklahoma City Thunder with two years left on his contract, and was never the same player after that. It was a fun time with Walker, but not a long time.

Former Boston Celtics point guard Kemba Walker

#3, Al Horford

Like Tatum, signing Horford to a big-money contract is something I’m sure most Celtics fans were (and still are) satisfied with. His first tenure in green started in 2016 when he agreed to a four-year, $113 million contract with Boston in a franchise-altering move.

The Celtics were in rebuild mode for a few years after the departure of Paul Pierce and Kevin Garnett, and the Horford deal was what solidified the team being back in the running. He was a vital part of the two conference championship appearances in his first three years in Boston before leaving in 2019 for the Philadelphia 76ers.

Eventually returning to Boston on a much cheaper contract, he continues to be a key to the team’s success years after his original blockbuster signing.

Given the above, it could certainly have gone a lot worse and it can't be said that the Celtics are bad at spending money. The future of Jaylen Brown could be the real decider in this matter, and his success or failure could be a watershed moment for the franchise.