Jaylen Brown's future highlights Celtics' offseason questions


After an incredible midseason turnaround ending with their first NBA Finals appearance since the 2009-10 season a year ago, many people viewed this season as Finals or bust for the Celtics, especially when the top-seeded Milwaukee Bucks were eliminated in the first round.

Wiggy's top 3 Celtics trade possibilities for the offseason

The C’s never made things easy for themselves this postseason, playing six games while facing elimination and in back-to-back seven-game series. Through it all, the Celtics persevered, coming all the way back from an 0-3 deficit to force a Game 7 in the Eastern Conference Finals, with a chance to become the first team in NBA history to win a series after falling down 0-3.

Instead, the C’s season ended in disappointing fashion with a 103-84 loss Monday night, as they became just another footnote in a long list of 151 teams that came up short after falling behind 0-3.

Now, an offseason that was supposed to be full of duckboats and champagne will instead be filled with big questions and some major decisions for Brad Stevens and Celtics ownership.

At the forefront of those decisions will be how the team goes about contract extension talks with Jaylen Brown, who by virtue of making second-team All-NBA this season is now eligible for a five-year, $295 million supermax extension. Brown, who has been noncommittal in the past when asked about his long-term future in Boston, did not shed much light on the situation following the team’s Game 7 loss to the Heat on Monday night.

When asked about potential extension talks this summer, Brown said, “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, I guess. I don’t really know how to answer that.”

Brown is now entering the final year of the four-year, $115 million contract he signed back in Oct. 2019, and is set to become an unrestricted free agent next summer. The biggest question will be if Stevens and Celtics ownership will be willing to give Brown the full extent of the supermax deal, especially after a very disappointing Eastern Conference Finals.

With Brown eligible for $295 million, and Jayson Tatum eligible for a five-year, $318 million deal next offseason, will Celtics ownership be willing to invest $613 million dollars to keep the duo together?

It would be hard to imagine Brown turning down the offer if it is made, but if for whatever reason he does, or if the Celtics' front office isn’t set on building the team around Tatum and Brown, that’s when trade talks can creep in.

Seeing as though they are both still in their mid-20s and have been to the Eastern Conference Finals in four of their six seasons together, it would make for a tough decision to break those two up, and it’s something the Celtics should not do.

It’s a cliché at this point that Boston only hangs banners for championships, but it is important to recognize the success these two have had. In just six seasons together, they have reached the Eastern Conference Finals four times. While not finishing the job with a title is frustrating, it should not be taken for granted the success these two have had, as they have established themselves as the best duo in the NBA, and again, are both in their mid-20s.

The coaching staff

It’s hard to imagine Joe Mazzulla won’t be back on the Celtics’ sideline next season. Mazzulla had his ups and downs this season, but Stevens has shown an ample amount of belief in the 34-year-old head coach.

Maybe some of his mishaps in the postseason will have the front office thinking of change, but it’s tough to imagine a scenario where Mazzulla isn’t back. If that’s the case, the team needs to surround him with some more experienced assistant coaches.

The Celtics did not do a good enough job solidifying their staff following the suspension of Ime Udoka, loss of Will Hardy, and loss of Damon Stoudamire in March. While it’s easy to blame Mazzulla, he did not have a lot of help around him and that’s an area the Celtics need to improve in this offseason.

Look for ex-Houston Rockets head coach Stephen Silas to be a name the Celtics look to add. Silas has been spotted around the Celtics facility since he was let go from the Rockets after three seasons with the team, and was even seen watching a Celtics practice with Stevens.

Grant Williams in free agency

After failing to agree to terms on a four-year deal in the $50 million range before the season, Grant Williams is set to become a restricted free agent this offseason.

It was a very up and down season for Williams, who was pulled from the rotation throughout the season before re-emerging in the postseason. It was reported by Marc Stein earlier this season that the 24-year-old forward would be seeking a deal worth up to $20 million annually, which could be a little steep for the Celtics.

As a restricted free agent, Williams can sign an offer sheet with any team, but the Celtics can retain him by matching the terms of that offer. In this case, it feels like a team with a little more cap space will outbid the Celtics when it comes to Williams.

Featured Image Photo Credit: Maddie Meyer/Getty Images