Celtics: Jaylen Brown's future at crossroads with upcoming contract talk

With the Celtics' season coming to an end, questions regarding Jaylen Brown's future with the organization loom large.

A season that was supposed to be filled with redemption and fulfillment for the Boston Celtics has ended in sheer disappointment. After losing in Game 7 of the Eastern Conference Finals to the Miami Heat, the Celtics now begin what will be a very important offseason for the franchise, especially given that they will need to make a decision on their All-Star duo of Jayson Tatum and Jaylen Brown.

Tatum is under contract for two more seasons before having a player option to decide on, but many are beginning to wonder if Brown has played his final game in a Celtics uniform. Entering this offseason, Brown has one more year left on his contract and is eligible for a supermax deal after being named to the All-NBA Second Team this season.

Brown had the best season of his now seven-year career, as the 26-year-old wing averaged 26.6 points, 6.9 rebounds and 3.5 assists per game while shooting 49.1 percent from the floor. Given the impact he brings on the defensive side of the floor as well, there is no denying that he is one of the better two-way players in the entire league.

This is a “what have you done for me lately” type of league, though, and what Brown did in the playoffs was very underwhelming given the Celtics' expectations. Brown's struggles against the Heat were very clear, especially in Game 7 when he committed a whopping eight turnovers and shot 8-of-23 from the field. But if Boston wants to keep him around long-term, they will have to pay a hefty price.

Jaylen Brown's contract situation

As a result of making the All-NBA team this year, Brown is supermax eligible, meaning he can receive a contract extension worth upwards of $295 million over the course of five years. If the Celtics were to give him this max deal, the two-time All-Star would make about $50 million during the 2024-25 season and then almost $66 million during the 2028-29 season with his contract numbers increasing by nearly $4 million each season in-between.

That is a massive amount of money for the Celtics to commit to one player, not to mention he is their second-best option alongside Tatum. The new CBA (Collective Bargaining Agreement) coming into play will also have heavy ramifications for teams who exceed the tax line like the Celtics would. Some of these restrictions include not being able to trade cash considerations and future draft picks, the loss of a team's mid-level exception in free agency, not being able to sign players via the buyout market and more.

If Boston views their All-Star duo of Tatum and Brown as their core moving forward and their best chance to win another title, then giving Brown this type of deal makes complete sense. However, this is the second consecutive season ending in playoff heartbreak for the Celtics, and the way it happened this season is why these conversations are being had.

Jaylen Brown on his contract after Game 7

With Tatum suffering an ankle injury early on in Game 7, the Celtics needed Brown to step up and take over. That unfortunately didn't happen, and Brown's performance is not what you envision of a player making $50 million or more per year. This is why Brown's future with the Celtics is very much up in the air this offseason.

“You asked what's my thought process? I really don't, you know, I don't even really know how to answer that question right now, to be honest,” Brown said immediately after Boston's Game 7 loss. “My thought process is take it one day at a time, focus on getting better. Focus on what the future holds and see where we are from there. I guess I don't know really know how to answer that.”

There is a lot that goes into contract negotiations between the Celtics and Brown entering the offseason. Obviously a player of his talents does not come around every day, which is why Boston needs to and is strongly considering working through negotiations with their All-Star. On the other side of things, they can not necessarily afford to keep Brown and Tatum together for the long haul, as they would both account for over $100 million on the team's payroll moving forward if they both received new supermax contracts.

Jaylen Brown trade options

Should the Celtics want to move on from Brown, they will have to try and find equal value or his talent, something that will not be readily available this offseason. Teams around the league are going to be scrambling to fix their rosters given the new CBA's financial rules. Since he is not viewed as a top-10 talent in the league, many teams will have a hard time coping with giving him $295 million over five years.

As The Ringer's Kevin O'Connor notes, Damian Lillard would be the picture-perfect trade target for the Celtics in a deal involving Brown. However, the Portland Trail Blazers have remained adamant on keeping Lillard and building around him, which almost shuts the door on that scenario. Trading for Anfernee Simons and the third overall pick from Portland presents opportunity for more depth, but could Tatum as the only All-Star talent on the team lead Boston to a title?

Bradley Beal from the Washington Wizards is another player the Celtics could possibly look to target in a trade involving Brown, but Beal has a true no-trade clause and it does appear that Washington under new president Michael Winger's leadership wants to keep their All-Star around. There are just no equivalent talents available right now that the Celtics could feasibly target and possibly trade for right now, which is why they are almost stuck with keeping what they have.

Jayson Tatum supports Jaylen Brown

Last season, the Celtics won 51 games and came up two wins short of a title. This season, the Celtics won 57 games and came up one win shy of the NBA Finals.

There is certainly a lot to like about this group, and winning 108 games with a Finals appearance over the last two seasons is more of an accomplishment than almost every other team in the league. However, winning a championship is the ultimate goal for Boston. The Celtics will have an awfully hard time doing so if they were to commit to max deals with both Brown and Tatum moving forward.

“It's extremely important,” Tatum said when asked about locking up Brown. “He's one of the best players in this league. He plays both ends of the ball and still is relatively young. And he's accomplished a lot so far in his career. So, I think it's extremely important.”

Entering the offseason, the Celtics have a massive decision to make with Brown's contract situation. If they extend him on a supermax deal, they are digging themselves into a financial hole But if they do not give him a new deal and let the All-Star play out the final year of his contract, there is a very good chance he will leave in free agency the following summer. Not to mention, Tatum has already come out and supported his teammate on getting a new deal, so losing Brown could ultimately wind up in Tatum growing frustrated with the organization.

Jaylen Brown is a key talent in this league, but something needs to change for the Celtics. Moving on from Brown and possibly parting ways this offseason could very well allow Boston to get the championship pieces and depth they are lacking right now.