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BOSTON, MASSACHUSETTS – DECEMBER 27: Jaylen Brown #7 of the Boston Celtics reacts during the second quarter against the Indiana Pacers at TD Garden on December 27, 2024 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)

It’s not often that basketball fans will read a ranking of players on a “five worst” list in some capacity and find a three-time All-Star and reigning NBA Finals MVP among the selections. That’s exactly what Boston Celtics followers saw on Sunday, as Bleacher Report’s Andy Bailey named star small forward Jaylen Brown for having one of the “5 Worst Value Contracts Right Now.”

Bailey has Brown as holding the fourth-worst deal in the league, with only Kawhi Leonard of the Los Angeles Clippers, Jerami Grant of the Portland Trail Blazers and Bradley Beal of the Phoenix Suns as having worse contracts.

The NBA writer explained that there were a multitude of ways in which he came up with his list of the five best and five worst contracts in the NBA.

“When analyzing whether a contract is good, several factors come into play. Age is important. Health history is huge. The length of the contract and the average annual value are obviously key, too. But one thing is unavoidable, and that’s subjectivity,” Bailey wrote. “So, with all of the above in mind, and while omitting both rookie contracts (whose values are determined by the league) and the league’s very best players (Nikola Jokić and Shai Gilgeous-Alexander obviously provide more value than their contracts suggest, but we’re operating in a world with salary caps and max deals)…”

“JB” inked a five-year, $288 million supermax contract extension in July 2023, a deal that passed Denver Nuggets superstar big man Nikola Jokic‘s $276 million extension for the most expensive in NBA history. Brown became eligible for the supermax extension after making second-team All-NBA during the 2022-23 campaign.

Bailey admits that his opinion that Brown has the fourth-worst contract in the Association may be “a little controversial” and it’s “not even a suggestion that the Boston Celtics shouldn’t have given him the extension they did.”

He adds, however, that his rankings are “strictly about value provided versus contract burden” and the California product’s deal has him as the sixth-highest-paid player during the 2024-25 campaign.

Why Brown Made Bailey’s List

Bailey calls Brown a “crucial part of a core that just won the championship” and includes the mention of his Finals MVP award. He also says the former No. 3 overall pick is “smack-dab in the middle of his prime” and “perhaps most importantly, had Boston not extended him, it might eventually lose him without a realistic way of replacing him (thanks to the salary cap and the current collective bargaining agreement).”

Still, despite Brown being a “good, probably even great, NBA player,” he’d need to be pushing the top-10 (like teammate Jayson Tatum) to justify his monster contract.

“He is not now, nor has he ever been, close to being the sixth-best player in the NBA. At 28 years old, it’s not likely he’ll become a top-10 player before 2029, when his contract expires,” Bailey wrote. “His 2024-25 production actually puts him in the top 50-60 range. His three-point percentage is well below average. And, as has been the case for years, his assist-to-turnover ratio is a very real concern.”

Brown had a solid first four seasons, including an eighth-place finish in the 2016-17 Rookie of the Year voting and a 10th-place finish in the Defensive Player of the Year tally in his second campaign. He made his first All-Star team during the pandemic-delayed 2020-21 season and finished with a career-best .397 three-point field goal percentage, before another solid year in 2021-22.

Arguably his best season was the 2022-23 campaign, however, when he not only earned his lone All-NBA nod, but his second All-Star honor and career highs in minutes (35.9), points (26.6) and rebounds (6.9) per contest, as well as free throw percentage (.765).

How Brown’s Responded Since Earning the Contract Extension

Following his big pay day, the 2016 draft pick responded by not only making his third All-Star team last season but shooting a career-high 49.9% from the field. Once the playoffs started, Brown stepped up even more, winning both the Eastern Conference Finals MVP and NBA Finals MVP hardware, surprising many and beating out Tatum.

The latter led the Celtics in nearly every notable statistical category during the championship round against the Dallas Mavericks, including minutes (40.2), points (22.2), rebounds (7.8) and assists (7.2) per game but struggled from the field (38.8%) and on three-pointers (26.3). Brown was second to Tatum in minutes (38.6), points (20.8) and assists (5.0) while leading the group in steals per contest (1.6). He had a better field goal percentage than his teammate (44.0%) but shot slightly worse from downtown (23.5%).

Brown is, again, second to the Duke product in a host of important individual statistics on the team this season, including minutes (35.6), points (24.1) and assists per game (4.7).

With Boston entering Sunday in second place in the Eastern Conference at 27-11, Brown may have another chance to prove his value this spring in the postseason.