NBA Notebook: Will Jaylen Brown finish his extension with the Celtics?

Jaylen Brown signed his super max extension on Wednesday alongside Brad Stevens, his agent Jason Glushon and Celtics ownership in a ceremony celebrating his career, off-court efforts, including the Bridge program that hosted the event, and future aspirations. The fact that he received the largest contract in NBA history came up several times, with Wyc Grousbeck mentioning how proudly he sat committing $304 million to Brown. 

"He's a true Celtic, he's a Celtic for years to come, we live and burn with the desire to make the world a better place, and as well, not to be forgotten, to win banner 18," Grousbeck said. "This is the next step to that, it happened today and you saw it right in front of you. I'm thrilled to welcome Jaylen as the highest-paid player in NBA history, one of the most talented and one of the people I respect the most who I've ever met." 

Both sides described a deal that made sense for everyone involved, and that's a fitting description for a staggering contract that shocked many and drew some ridicule after Brown struggled in Boston's East finals loss. Re-signing Brown bought the Celtics time, gained them six years of team control and allowed for flexibility into the future while accepting risk at the later end of the deal, when he'll make close to $70 million. There's no doubt Brown exploded past his market value in this deal, where no other team could offer him anything close and injuries to players like Paul George, Kawhi Leonard, Kevin Durant and LeBron James allowed him to become eligible for historic money. It's also why the league agreed to such a system. 

Being able to offer that money allowed Boston to keep Brown well before free agency became a relative lock. They probably could not have extended him with the 140% raise on his $30-million salary the league introduced prior. He would've played out that final season in pursuit of All-NBA if he missed that distinction last year, setting up anxiety on both sides. Remember why the team and fans advocated for him to make the team? It's so the Celtics could offer him this contract. Including a trade kicker ceded some teams as well, though the deal having no player option stands as a larger win for the Celtics in negotiations -- the first supermax deal in NBA history not to include one. 

As I wrote previously, Brown would always make the full max. It's the cost of not going to free agency, risking losing Brown and maintaining the most team control. The big question is how the Celtics make the money work while building around three high-paid stars and Derrick White due a raise too. Soon, Brown's deal won't rank as the largest in NBA history, but Jayson Tatum's projects first to exceed Brown's at approximately five years, $318 million, an extension he can sign next summer. 

Giannis Antetokounmpo's next super max with the Bucks, which he can agree to next summer, Luka Dončić's in 2025 and Nikola Jokic's in 2026 could all push closer to $400 million as superstar salaries start barreling toward $75-million in average annual value by 2030. That's not to say Brown's deal will become some bargain, he needs to reach heights on par with the league's best after an analytically uneven season and one where he struggled with Tatum off the floor. He's not on par with the league's top-end talent yet. If he struggles to take steps with that responsibility, the Celtics will face tough decisions in 1-2 years. 

"I don't shy away from pressure," Brown said this week. "I know what the demand is, I know what the expectation level is and I know the work that's required. Everything about me is about work. I look at it as just another challenge to get better, another challenge to improve. I don't think anybody's seen my best yet." 

Brown signing his deal provides a solid financial roadmap for the team into the future. They'll likely avoid the second apron and its associated penalties this season, currently $3.4 million short of that line between 14 players. Their luxury tax bill comes in at roughly $20 million, actually down from last year significantly due to Al Horford's pay cut to $10 million. Brown makes $31.8 million in the current year of his deal, and Tatum remains a bargain for two more seasons averaging $33 million. 

Next year, though, Brown spikes to over $52 million, with Kristaps Porziņģis and Tatum combining for $64 million. A Malcolm Brogdon trade becomes far more feasible at that point, entering the final year of his contract ($22.5M), but a White extension could offset those savings. A third consecutive year in the tax will trigger repeater penalties, while 2024-25 will also become the team's first spent above the second tax apron line. 

We've discussed the penalties before, a frozen draft pick seven years out (2032), dollar-for-dollar trade matching, no sign-and-trade additions, no buyout signings and no mid-level exception signings are allowed. Those aren't entirely prohibitive, Boston owns its first-round picks from 2024-2027 to provide some cost control to the roster, and 2029-2031 would remain for more aggressive additions. The tax is a larger concern for the franchise due to its revenue streams falling beneath teams like the Warriors, Nets and soon the Clippers, who own their arenas with richer ownership groups. Stevens said all summer he has the green light to add, spend and pursue a championship at all costs. Eventually, there'll be some limit. 

"We're trying to win, and everybody's very supportive of that from top-down," Stevens said. "It starts with Wyc and (Steve Pagliuca) and our ownership group, and we're trying to win, and we're going to do our best to put our best foot forward to do that. The required part is the right talent to build around. We're very fortunate to have a lot of talented players. Obviously, Kristaps is sitting up here, Jayson and Jaylen have been mentioned a ton, we've talked about Al and Rob, we haven't even mentioned Derrick and Malcolm, right? And Payton (Pritchard). We've got guys that are under contract who are really, really good players. So building a team around that, that all fits together in the best way we can is what we're trying to do. It's about winning." 

That line likely arrives in 2025-26. Tatum will begin his supermax at roughly $55 million (35% of the expected 2026 cap). Brown's salary will increase to over $56 million and Porziņģis enters the final season of his extension at $30.7 million. Those three contracts alone will approach the salary cap line, with Robert Williams III's final season on his deal, White's first on a new deal, Payton Pritchard on a roughly mid-level extension and whatever draft picks, trade additions from the prior two years and minimum contracts rounding out a roster now facing repeater taxes (which include a 5.5x multiplier for each dollar spent $10 million over the tax, and 6.5x multiplier for each dollar over $15-million). 

With a White extension starting around $26 million, at most, and Pritchard's projecting around $13 million that season and two late first-round picks combining for around $5 million. Those eight players, plus Jordan Walsh would make about $200 million alone, just under the second apron line. Improving that roster becomes difficult and perhaps unfeasible. 

The biggest question that emerged from Brown's extension becomes whether he'll finish the deal, projected to run through 2029, in Boston. It's hard to say now. The Celtics are intent on building long-term around Brown and Tatum. If they ideally improve, become champions over one or both of the next seasons and have players who can carry a less-talented roster around them, they're a near lock to play together beyond 2026. Boston could try to break up Porziņģis' expiring contract into two or more role players to balance the roster. Maybe Williams III will emerge as a starter worthy of his own extension at that point and the team can move on from its new star big. The odds lean against a Brown and Tatum marriage through the end of the decade though. That could stem from a money crunch, another needed shakeup after falling short of titles, or Brown's own decision to ask out. 

The Celtics acquired protection against the latter by excluding a player option from his deal. Say Brown wanted out around 2026, he'd still have three years left on his contract, giving Boston some leverage to deny, postpone or receive a significant return for Brown. That's why the deal took nearly one month to negotiate, Brown gaining his own protection against a later trade in the form of a trade kicker, which still hasn't been reported but The Boston Globe's reporting and the lack of a leak indicates it's well beneath the 15% allowed for a player. It's not a no-trade clause, but could allow Brown some say in a potential deal in the later stages of his contract. That give-and-take over a hypothetical exit later in this contract at least signals an admission over how business goes in this league, something Brown spoke about in his Ringer interview. Teams will trade you. Players will ask out. 

"I think (negotiations) went great," Brown said. "A lot of times, when you talk about a relationship you have with individuals, you can just talk to them normal or direct, because I've known these guys for seven years, and a lot of times, when financial stuff gets into play, it gets a little more sensitive or etc. From my standpoint, they understood where I came from, we understood where they came from and it was all about meeting it in a place where it made sense for everybody. I'm glad that we were able to finish it and get everything done." 

The trade kicker doesn't mean much in the short term. Brown cannot be traded until July 26, 2024 and barring disaster will probably play out Tatum's final season on his deal in 2024-25. A player can't make more than his max contract, so even if Brown were traded in 2025, he'd earn no trade kicker if his salary increase exceeds the cap's growth as projected (over 35% of cap from 2025-2027). In 2028, he'll likely dip below the league max salary value, allowing him to earn whatever difference there is between that salary and the max over his final two seasons, if traded. 

That kicker, likely no more than a few million dollars annually, does count in trade math, so at that point Brown holds some leverage by being able to waive that trade kicker to allow a deal. Kyrie Irving did the same to allow his trade from the Cavaliers to the Celtics in 2017, when he could've received a nearly $6-million salary bump in the deal.

Trade kickers may become more valuable in the new CBA, where second-apron teams like Boston at that point must match trade money exactly. Those teams also can't aggregate salary to complete a trade, the team trading for Brown may brush up against the second apron while doing so, or face their own issues in matching salary in a deal. 

It's tough to forecast how significantly the trade kicker could come into play years from now. Its inclusion signals that while Wednesday marked a day of optimism for a long union between Brown and Tatum, it also signaled urgency to prove they can thrive together as champions. Four conference finals and a Finals run in six years proved suitable at their old salaries with tons of talent around them. It won't on the new deals.

"In terms of having Jaylen here, from my personal perspective, and I speak for the front office, teammates and fans, I think I speak for everybody, he's a key," Grousbeck said. "Jaylen has stood tall for seven years here, improving, to my mind, every single year with hard work and with true talent. We want to go win on the basketball court as well. It's entertainment, it's the fun part of the job, there's a lot more work to do than just that, but we intend to go do that, and having our All-NBA Jaylen Brown here, enthusiastically ready to build and ready to grow from here off the court and on the court, it's a great day for the Boston Celtics." 

Here's what else happened around the NBA this week...

Boston: Joe Mazzulla agreed with Brown on his defense-first point, announcing Derrick White will start alongside to two big men while the team pursues a new identity. Malcolm Brogdon remains on track to return in time for training camp, Mazzulla said, though admitted a healing process is underway after the trade that nearly sent him to the Clippers. Longtime team broadcaster Mike Gorman announced he'll retire after the 2023-24 season. 

Brooklyn: Ben Simmons' return looms in time for training camp as Makil Bridges hyped up Simmons' return to star form after he spent the last year recovering from back injuries and surgery. Marc Spears reported on ESPN that Simmons checked every box this summer as his recovery progressed, and said Simmons feels healthier than he has since his final season with the 76ers -- a near defensive player of the year campaign. Ian Begley added that Simmons' rehabilitation ended recently, and he's now exclusively focused on skill work and conditioning for the rest of the summer. Simmons enters the first of two years remaining on his contract with an average annual value of $39 million. 

“I think his back was messed up, and him actually going through, getting X-rays and them telling him you had to get surgery, I think it felt good for him because I think people didn’t believe him,” Bridges said on Paul George's podcast. “Maybe in Philly, he was the little boy who cried wolf sometimes, so he didn't wanna play or some s***, and now he would say, ‘I’m hurt,’ and people are like, ‘F*** outta here.’ But now he’s actually hurt, but people still don’t believe it. So he was actually hurt and now he’s got surgery, and he’s getting back, but he loves the game." 

Chicago: A packed, stagnant roster enters this season close to the luxury tax line, one NBC Sports Chicago reported the team will not want to cross by the end of the season. That's relevant as forwards Javonte Green and Derrick Jones Jr. remain in free agency after Ayo Dosunmu signed a $21-million contract with the team, a deal The Athletic considered a necessary overpay. The Bulls maintain two open roster spots and appear likely to waive Carlik Jones, freeing up another and roughly $2 million more in room beneath the tax. Torrey Craig is an early favorite to start at the four, while Patrick Williams will have to battle off their bench as he enters his rookie contract's final year as a key to Chicago's future. 

Cleveland: When the Cavaliers traded for Donovan Mitchell, they not only sacrificed their future draft capital, they did so with Mitchell only under contract for three more seasons. Now, two summers from free agency, Mitchell could easily leverage his way out of Cleveland if the situation sours this season, setting up a crucial season where the team needs to build on its disappointing first-round exit against the Knicks. Adding Georges Niang, Max Strus and bringing back Caris LeVert helps some. Emoni Bates showed Summer League promise, but the wing position on this team still looks a little too weak compared to the other east contenders like the Celtics, Bucks and Heat. The Cavs are reportedly all in on keeping him.

“They’re doing their best to reconfigure things around him and just keep rolling out the red carpet, making sure he knows he is taking care of, all of that,” a source said. “No one is hitting the eject button on this. There is a lot of cost that’s been sunk into him and they’re going to push forward.”

Golden State: Enjoy watching Steph Curry, making the media rounds for his new documentary, thrive on the Hot Ones podcast. He also recently discussed his relationship with LeBron James, his rival across four straight NBA Finals, the only championship rivalry stretching over that many seasons in the history of the four major North American sports leagues. Those years saw quiet tension between the two, before the legacies they established during those years led to more acknowledgment between the two greatest players of this generation. 

"It's complex," Curry said. "Because you go from playing in the tournament and him coming to watch, to me coming in as a young rookie in the league and him giving me advice on how to get through some of the early struggles that I was gonna go through as a player, to the four Finals appearances in a row, playing against each other, to even last year playing in the playoffs again. He's a great dude, great friend, great competitor."

Indiana: T.J. McConnell continues to draw interest on the trade market after falling behind other Pacers guards and suffering from injuries in recent seasons. The Pacers backup guard still plays some of the position's feistiest defense across the league and sets the table well as a passer, and makes sense in the Suns' backcourt. He earns $8.7 million this season before a partially guaranteed $9.3-million final season in 2024-25. McConnell appeared in 75 games and shot 54.3% from the field. He wants to remain with the Pacers, but could prove one of the late offseason steals if someone acquires him. Former Celtic Daniel Theis, still with Indiana from the Malcolm Brogdon trade, will play for Germany in next month's FIBA World Cup.

Clippers: Not pushing hard enough to land James Harden, from the Philadelphia perspective, as one of the two major outstanding trade requests holding up the later stages of the offseason. As I start thinking about what Harden would look like playing alongside Russell Westbrook, Kawhi Leonard and Paul George, it's one of the more intriguing early NBA stories. Beyond the injuries, they'd play small often, all four players need the ball, and while the spacing's great on the Clippers, Westbrook would need to play some center offensively as a roller. He hesitated to do so with Lakers and played his best basketball with the Clippers back on the ball while George and Leonard missed time. Getting P.J. Tucker as a small ball five from the Sixers would help. Still, it's hard to imagine that group winning the West.

Lakers: LeBron James' 18-year-old son Bronny suffered cardiac arrest at USC on Monday in a workout ahead of his freshman season playing for the school. He left Cedars-Sinai Medical Center after a brief stay in ICU to rest at home after a 48-hour stay, with a rapid medical response likely saving his life in a terrifying moment that called back to Celtics star Reggie Lewis' death 30 years ago this week. Merije Chukumerije, the cardiologist overseeing James, said his workup is ongoing and the hospital's medical staff is encouraged by his progress so far. It's unclear what caused the heart ailment, or whether it'll threaten James' basketball career which gained significant traction in recent years as LeBron forecasted eventually playing alongside Bronny in the NBA. He starred at Sierra Canyon High School in Los Angeles before committing to USC over Memphis and Ohio State. LeBron offered a statement online expressing thanks, reserving further comment for later. This week, Jeanie Buss announced LA will retire LeBron James' number after he retires. 

"I want to thank the countless people sending my family love and prayers," LeBron wrote Thursday. "We feel you and I'm so grateful. Everyone doing great. We have our family together, safe and healthy, and we feel your love. Will have more to say when we're ready but I wanted to tell everyone how much your support has meant to all of us."

Memphis: Jaren Jackson Jr. spoke for the first time following Ja Morant's suspension about the team's path ahead without him for 25 games at his children's summer camp. Jackson praised the team's trade for Marcus Smart to fill Morant's role and defend alongside Jackson as the only defensive players of the year uniting in league history. Jackson will also star for Team USA, likely as their starting center, and may face teammate Santi Aldama and the defending champion Spanish national team in the FIBA World Cup next month. As for Morant, Jackson isn't worried about him. 

“That’s 12,” Jackson said. “He’s going to be the same always, and he’s going to run the league when he gets back.” 

Milwaukee: Re-signed forward Thansasis Antetokounmpo for a fifth season with the Bucks after he nearly left brother Giannis Antetokounmpo to rejoin the Knicks organization he began his NBA career with. Thanasis will headline Greece's FIBA World Cup roster, competing in the same group as the US, without Giannis, who will sit out after undergoing offseason knee surgery. The signing rounds out the Bucks' roster at the regular season max of 15 standard contracts, including another pair of brothers reunited between Brook Lopez and free agent signing Robin Lopez. Kostas Antetokounmpo will play for Panathinaikos in Greece this season while 21-year-old brother Alex Antetokounmpo spent last year with Milwaukee's G-League affiliate. 

Minnesota: Karl-Anthony Towns will make his FIBA World Cup debut for the Dominican Republic next summer, listed as part of the country's tentative roster for next month alongside Kings guard Chris Duarte, Warriors guard Lester Quinones and Celtics center Al Horford. Towns previously represented DR in international competition when he was 17 years old in 2012. Horford, last I heard in the fall, appears unlikely to actually suit up for the tournament and while Towns committed, the official roster won't come out until next month. Anthony Edwards will headline Team USA's starting lineup. Towns was born in New Jersey to his Dominican mother Jacqueline Cruz, who died from COVID complications among numerous family members in 2020.

Philadelphia: James Harden spoke with USA Today briefly alluding to his ongoing trade request, indicating he's focusing on doing his job and staying out of the way. Harden also discussed the league's new anti-flopping rule, Damian Lillard's trade request and soccer. The 76ers reportedly want to comply with Harden's trade request, but will enter training camp with him on the roster if Daryl Morey doesn't find a deal suitable for the team, following his playbook from the Ben Simmons saga. Harden appears far more amicable to showing up. Will Philadelphia receive his best effort when he does? 

The Sixers also announced plans to privately finance their new downtown arena plan, one causing controversy in Philadelphia for its intrusion on Chinatown. 

Phoenix: Bradley Beal spoke to Slam about his trade to the Suns, which he initially thought would send Devin Booker to the Wizards as he narrowed his no-trade request to Phoenix to play alongside Kevin Durant. Instead, the Suns sent Chris Paul and draft capital, forming the league's best scoring trio and an intriguing new power in the west. Beal also vowed to return to being one of the best two-way players in the league this season. 

“I was like, Why are they trading Book? Like there’s no way that this is happening,” Beal said. “Like, this can’t be, this isn’t right. But fast forward, he’s here, I’m here and Kevin’s here and DA [Deandre Ayton]’s here. It’s surreal and crazy to think about how the deal even came to fruition, but it’s done and I’m in an awesome situation where I can compete every single night for a chance to win.”

Portland: What's next after reports that the NBA could fine or even suspend Damian Lillard for continuing to pressure the Blazers to send him to the Heat? The most likely answer is a return to Portland for now, with a decently competitive roster lined up to begin the season alongside top selection Scoot Henderson and backcourt mate Anfernee Simons. The team brought back Jerami Grant and Shaedon Sharpe should take steps into his second season. It's not a west contender by any means, but time could allow the franchise to convince him to commit long-term again or find a new deal that'd return the Blazers more than they're currently capable of pulling from the Heat. The Nets always made sense to me. Nothing will happen quickly. 

Toronto: Bobby Marks considers OG Anunoby the next intriguing test for the CBA's new extension rule, which allowed players to receive up to a 140% raise on the final salary of their current contract, compared to 120% under the previous rules. Domantas Sabonis and Dejounte Murray became the first players to extend under those new parameters, while that would've dictated Jaylen Brown's salary if he didn't make All-NBA and become eligible for the supermax (starting at $44.5M, roughly $200-million over four years). Anunoby's potential new deal with the Raptors would net him four years, $116 million, adding $16 million compared to the previous CBA. If Brown would've signed his deal with Boston, it would've helped the Celtics remain flexible, but my bet it he would've gone to free agency aiming for an All-NBA season instead.

Washington: Former Celtic Danilo Gallinari expressed excitement over returning to the floor with the Wizards this year, ending speculation for now about a contract buyout that seemed imminent after the Kristaps Porzingis trade earlier this month. Rumors pointed toward Gallinari joining the Heat, which would've boosted Miami's frontcourt if Gallinari returned to form. It's unclear where Gallinari stands in his recovery from ACL surgery in September, ending his first season with the Celtics shortly after signing the deal. He'll play alongside Mike Muscala in Washington on a team that can offer him plenty of minutes and a chance to rebuild his value for a contender that could pursue him closer to the deadline. Gallinari told BSJ last season his focus remains on playing a much longer basketball career, rather than trying to get back on the court for a final run.