What Brad Stevens must address to fix the Boston Celtics

The Boston Celtics' 2020-21 season came to an end on Tuesday night in disappointing fashion as the Brooklyn Nets bounced an injury-riddled squad from the first round of the playoffs in five games. On Wednesday morning, what was shaping up to be an already interesting offseason for Boston exploded in a way no one could have imagined.

Danny Ainge retired from his role as the Celtics' president of basketball operations. That part was surprising, but not entirely shocking. Ainge has hinted several times in recent years that retirement has been looming. He’s talked about his family being worried about the stress of the job, given his health concerns. This season, in particular, Ainge has said a handful of times, “I don’t know how much longer I’ll be doing this.” It’s no surprise that he’s following through and is moving into retirement.

His replacement, however, is a major surprise.

Brad Stevens was brought in to replace Doc Rivers as the Celtics' head coach in 2013, just as Boston was kicking off a rebuild. Eight years later, Stevens is moving upstairs to replace Ainge. Given that there was never any indication Stevens wanted to do anything but coach, this one is a shocker.

Stevens takes over the front office as the Celtics hit a bit of a crossroads. For several years, Boston vacillated between being the scrappy underdog and the young, but talented upstart. That shine has come off a bit, as the Celtics turned in a perfectly average season before being trounced in the first round of the postseason.

As with all talented young players, even ones who are signed long-term as Jaylen Brown and Jayson Tatum are, there is a sense of a ticking clock. If you don’t prove to be contenders quick enough, those players start dropping hints about leaving to win elsewhere. Wait too long, and you risk losing them for nothing. Neither Brown nor Tatum have said anything of the sort to this point, but another season or two of mediocrity and the chirping will begin.

Ainge is walking away, having built one title team and having given the Celtics the building blocks for another contender. Now, it’s up to Stevens to figure out how to maximize Brown and Tatum, beyond X’s and O’s. He has to build a roster to support his two young All-Stars on their way to title contention.

Jaylen Brown and Jayson Tatum talk during a game.
How will Brad Stevens build around All-Stars Jaylen Brown and Jayson Tatum? (Maddie Meyer/Getty Images)

Who will Brad Stevens hire as Celtics coach?

But first, Stevens has to hire his own replacement.

At last count, approximately 20 different names have been floated as the next Boston coach. They range from the simple solution of promoting lead assistant Jay Larranaga to the crazy suggestion that Mike Krzyzewski is “retiring” from Duke to take over the Celtics.

It wouldn’t be a surprise if the Celtics go completely off the board and hire someone no one is thinking about. That’s what they did with Stevens.

The important thing: Stevens has to get this hire right. This is arguably the most important thing he will do in his initial set of moves as Celtics PBO. If Stevens misses, every time Boston has a four-game losing streak, there will be calls for him to take back over. Or worse, there will be screams for Stevens and his handpicked successor to be shown the door.

After he hires a coach, Stevens has to get to work on the roster. In the news conference announcing the transition, Stevens said, “I have a really good sense of what our team, and the guys as individuals, do well and don’t do well.” That pairs well with some of his comments throughout the playoffs about maximizing talents and putting players in a position to succeed.

For some current Celtics, that position may be on another team.

Kemba Walker key to other roster moves

A lot of what Stevens will be able to do roster-wise will depend on what happens with Kemba Walker. Walker is owed over $73 million through 2022-23, assuming he picks up his player option for that season. That’s a lot of money for a small guard with knee problems that prevented him from completing a playoff series.

In his old role as coach, Stevens may have preferred the team move Walker for more win-now help, even if it cost the team a combination of young players and/or draft picks to get off Walker’s salary. Coaches always have a more short-term view.

Now, Stevens has to balance the desire to compete right away against the future of the Celtics. If he believes it’s in the best interest to ride it out with Walker and hope for the best health and production-wise, then Stevens will keep Walker. If he can find the right deal to bring in help now, while cleaning up the cap sheet, Stevens will move Walker.

Kemba Walker dribbles the ball during a game.
What the Celtics decide to do with Kemba Walker will inform many of their other roster decisions. (Steven Ryan/Getty Images)

While figuring out the Walker situation, Boston will also be looking how it should handle Evan Fournier’s free agency. Ainge made a significant investment in acquiring Fournier, because he used $17 million of the Celtics' $28 million trade exception from the Gordon Hayward deal last offseason to make the deal happen.

If Stevens views Fournier as a major piece, as either a starter or sixth man type, Boston has a leg up on re-signing him. The Celtics have full Bird rights, but Fournier’s contract demands shouldn’t reach a point where that really matters. There also isn’t a clear suitor for him among the cap space teams this summer. Whether or not Stevens re-signs Fournier will be an indication of how he views his roster building moving forward and Ainge’s moves as his predecessor.

The next question is what to do with Marcus Smart? Smart is a wildly talented defender and the heart and soul of the Celtics. He’s also a somewhat limited offensive player who is a very streaky shooter. In many ways, Smart is a modern version of John Starks. When he’s on, you’re going to win. If he’s off, he might shoot you right out of the game.

Smart has one more year under contract. That gives Boston some options. The Celtics can give Smart an extension and keep him with the Celtics for the rest of his career. They can trade him. Or they can let things play out and see if he turns in a big season in a contract year. Stevens was the one who coined the term “We love and trust Marcus,” so it would be a bit surprising to see Smart moved.

Danny Ainge's final draft classes need development

Up front, the Celtics don’t have a lot of depth. Tristan Thompson is under contract for another year, while oft-injured big man Robert Williams is extension-eligible for the first time.

Without directly saying how much he loathed having to play two bigs together for most of the first half of the season, Stevens made it clear that’s not how he views a successful team. Stevens prefers to play one big at a time, while having versatility and switchability on the floor at the other positions. That could make Thompson an interesting piece for salary-matching in a trade, given his $9.7 million expiring contract.

Williams is a different story. If the team could trust him to stay healthy, it would be a no-brainer to give Williams a hefty contract extension. We’ll come to learn where Stevens falls on this issue fairly quickly.

And then you have the kids.

Romeo Langford, Grant Williams, Aaron Nesmith and Payton Pritchard were all drafted in the first round of the last two drafts. They represent the final haul of Ainge’s once overflowing treasure chest of draft picks. Stevens spoke at length about how important this offseason would be for the younger players, as they’ll have a chance to really work on their games after two straight disrupted summers.

Langford has battled health issues for his first two seasons in the league, but has flashed potential as a wing defender and slasher on offense. Williams projects to be a solid, but unspectacular frontcourt reserve. Nesmith had a rocky rookie season, but improved greatly as the season went along. Pritchard is the most finished product of the four and projects to be at least a high-end backup point guard.

Romeo Langford holds the ball in his hands during a game.
Romeo Langford has battled health issues over his first two seasons with the Celtics. (Steven Ryan/Getty Images)

Will Jaylen Brown, Jayson Tatum remain in Boston?

Lastly, would Stevens be bold enough to split up the All-Star duo of Brown and Tatum? More than anyone, Stevens should have a handle on the fit of the two young stars and their potential to lead Boston to a title.

It’s likely Tatum will stay. His current standing in the NBA hierarchy and his continued upside are just a notch ahead of Brown’s. But if Brown could be the headliner in a package to return a superstar to pair with Tatum, would Stevens pull the trigger that Ainge was hesitant to?

Celtics primary governor Wyc Grousbeck said that when he talked to Stevens they agreed they’re in this relationship for the long haul. Grousbeck said both he and Stevens will “win banner 18 or we’ll die trying.”

It’s a new era of Celtics leadership, but the goal remains the same. For a long time, Celtics fans were convinced Brad Stevens would be the guy to get Boston back on top. He may still be. It’ll just be in a very different way than anyone ever imagined.

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