In the summer of 2023, Jaylen Brown inked what was, at the time, the most lucrative contract in NBA history — a five-year extension with the Boston Celtics worth up to $304 million.
The deal eclipsed the previous high-water mark set by Nikola Jokic 's $276 million extension, pushing JB to the financial summit of the league.
But as the ink dried and numbers reverberated through the sports world, the discourse turned into loud debates. For all the millions being handed out, not everyone was convinced the Boston star belonged in that tax bracket.
Among the various eyebrows that were raised was Hall of Famer Charles Oakley. Oak believed at the time that it was too much money for a player who was just another star on a championship roster.
" Jaylen Brown , I mean, he is a good player," Oakley said . "But for a guy who get paid $300 million, he should be a top 10 player in the league. I don't think he a top 30 player in the league."
Those weren't words delivered in haste or out of spite. Oakley, who carved his reputation as one of the most no-nonsense enforcers in the league's history, built a career on calling it exactly how he saw it. Charles' critique was sharp, but it wasn't without grounding. Brown entered the league in 2016, selected third overall by the Celtics.
One year later, Jayson Tatum joined him, and together, they formed a potent, versatile wing duo. They anchored a Celtics team that consistently made deep playoff runs, making Conference finals appearances in 2017, 2018, 2020, and 2022.
But despite the promise and the pedigree, something always seemed to be missing. The team's inability to get over the hump led to mounting speculation that the Brown-Tatum partnership, while exciting, was more smoke than fire when it came to delivering championships.
The Celtics brass, however, stuck with their core. And when JB's rookie extension window came calling, they didn't blink. $304 million was the price of belief — belief that Jaylen would eventually lead or at least co-lead Boston to the promised land.
The numbers raised questions. Prior to the contract, Jaylen had just two NBA All-Star nods to his name — no MVP talk, no All-NBA First Teams. He hadn't led the league in scoring, assists, or steals. The contract was a gamble on potential, continuity, and internal growth from Brown, who remains one of the league's top two-way talents.
JB's resume may have lacked the heavy-hitting accolades typical of a max-contract star. He had been to the Finals once in 2022, where Boston fell in six games to the Golden State Warriors . In that series, Brown was good — perhaps even the Celtics' most consistent offensive weapon, but not transcendent.
"You are not going to put him there because they're making the money," Oakley said.
Yet, if 2023 was the year the money started flowing, 2024 was the year Brown answered the world.
In the 2023–2024 season, the Celtics surged through the league, finishing with a 64–18 record. The team, finally firing on all cylinders, made quick work of their playoff competition. Then came the redemption: a 4–1 NBA Finals series win over the Dallas Mavericks , with Jaylen stepping into the spotlight.
He averaged 20.8 points, 5.4 rebounds, and 5.4 assists in the Finals, holding former Dallas star Luka Doncic to a subpar shooting series with his defensive tenacity. The stat sheet told one story, but the film told another — JB had become the tone-setter, the anchor, the closer.
Jaylen was named Finals MVP, finally giving the Celtics their 18th championship banner, breaking the tie with the Lakers for most in NBA history. For Boston, the investment paid off. For Brown, it was validation. His contract remains among the highest in NBA history, though his teammate Tatum eventually surpassed him with a new deal in 2024.
