As the 2023 NBA Draft approaches, will the Celtics make a trade to reshape the roster?

The Celtics have a crowded backcourt, but is it a stretch? That’s the question shaping the franchise’s plans as the trade season heats up toward Thursday’s NBA Draft.

Derrick White was a revelation last year, Marcus Smart continues to be a core figure in the team’s leadership structure, while Malcolm Brogdon won Sixth Man of the Year by lighting it up off the bench until an elbow injury derailed his conference finals. Payton Pritchard occasionally watched the court while battling short auditions for the rest of the league.

Now something has to change. Pritchard switched agents to Austin Brown of CAA after he wasn’t moved at the trade deadline, a potential move to get out of Boston and onto a team that can give him the opportunity he earned during the 2022 NBA Finals.

Brogdon, who also happens to be represented by Brown, wants to remain in Boston and remains optimistic he will avoid surgery on the tendon he tore in his left elbow against the Heat, according to sources familiar with Brogdon’s thinking and who granted anonymity because they were not authorized to speak on the record. Team personnel around the league have long assumed that one of those point guards will not be with the Celtics in the coming weeks as the team prepares to offer Jaylen Brown a 5-year, $295 million supermax extension.

Whether it’s Brogdon or a package of Pritchard and Danilo Gallinari, the Celtics have the salary to make a deal that will reshape their frontcourt if restricted free agent Grant Williams signs an offer sheet they won’t match. But if Williams is going to be priced out of Boston’s market, it will likely be driven by a team without cap space.

There have been more than a half-dozen teams that have inquired about a potential sign-and-trade deal for Williams, league sources said. Athletics. Williams turned down an extension offer around the expected $12.2 million mid-level exception (MLE) before last season, and despite a tumultuous year in and out of the rotation, there appears to be a market brewing that could push his value beyond the MLE. most teams over the cap could offer.

While there has been speculation about various sign-and-trade frameworks that could bring in useful assets, these kinds of trades for restricted free agents don’t often produce significant returns. A recent exception was when Houston traded the rights to Isaiah Stewart to Detroit for Christian Wood in 2020, but Detroit also received a protected future first-rounder to even things out. But these deals often involve dumping salaries, second-round picks, or simply establishing a trade exception.

Boston’s position in negotiations around the league has generally been that the organization wants to resign Williams and keep Brogdon, but this front office tends to play their cards close until a deadline like the draft or free agency approaches and then be more open to acts. But the reality of the looming second apron (aka supertax) and the team’s current construction make it hard to justify paying over 10 percent of the salary cap to a player who isn’t a lock in the rotation. Having your highest paid big come off the bench just doesn’t make sense, especially on a team that has long tried to maximize value at the center position.

Head coach Joe Mazzulla must be committed to playing him in a way that wasn’t even close last season to justify the contract. Milwaukee has expressed great interest in Williams in the past, and new Celtics assistant coach Charles Lee is a fan of Williams, so the big man can have a different experience in Boston this coming season. Williams’ position coach Ben Sullivan is headed to Houston, while assistant coach Aaron Miles and player reinforcements coach Jarrell Christian are still weighing their futures, according to team sources. If Williams stays, it could be a more favorable situation that allows him to play through his mistakes and find a rhythm.

In restricted free agency, teams often have to balance maintaining a good relationship with a player’s agency and taking advantage of their influence. While it would be ideal to solidify these players and let them get their opportunity elsewhere, the Celtics don’t have much they can count on in their big man rotation.

Al Horford. (Jerome Miron/USA Today)

Al Horford signed a fully guaranteed two-year extension that starts now, so the team already has a 3-and-D big locked up. But asking him to still play 30 minutes per fight that starts at the age of 37 seems unsustainable.

He’s looked out of sorts at times over the last two postseasons, but eventually had sharp defensive drop-offs deep into the run that showed why his minute load needs to be lower throughout the regular season. Robert Williams III could only manage 20 minutes a night in the playoffs and has dealt with injuries his entire career, so can he handle a bigger role in the future?

With Pritchard looking for a fresh start elsewhere, the Celtics have to start developing future rotation players at some point and can’t afford to lose Grant Williams without picking up another draft pick or young player. So even if he signs an offer sheet they can’t afford long-term, the best move might be to match the sheet and then make a trade to shed salary before next offseason.

There isn’t a drive to avoid the second front only for salary management this season, as they already have a second-round pick and don’t have room in the current rotation for another signing of the Tax MLE. But when the draconian draft pick penalties start next summer, that’s when the Celtics may have to start implementing austerity.

A key part of Boston’s roster-building strategy will be targeting high second-round picks that were thrown around at the league’s final deadline before the new CBA suddenly made them even more valuable. Competing teams in the super tax whose first-round picks fall in the late 20s might look to move down a few spots to the second round so they don’t have to pay the guaranteed four-year rookie-scale deals that goes to first-rounders.

Players drafted in their 30s tend to sign deals with two years guaranteed and will often sign for the minimum. Even saving a million dollars can be important for a team trying to manage around the second apron.

The notion that Boston needs to trade one of Brogdon, Marcus Smart or Derrick White because of some kind of logjam doesn’t pan out. Everything about the way this team plays on both ends makes it important to have three big point guards who can handle the ball and defend. Brogdon was brought in as a luxury last season and was exactly that. He wasn’t a consistent matchup closer or lead the offense, but he was brought in to score and defend other ball handlers. It worked well until injuries spoiled the ending.

The Celtics need more frontcourt depth, but at that point you’re opening a wound to bind another. White took an offensive step forward, Smart took a defensive step back. This backcourt is pretty much in the same place it was under Ime Udoka, just good enough to work when Jayson Tatum and Jaylen Brown are playing their best.

The super tax does the building of a deep team, as over the last few years Boston has played a relatively short-term game. That makes the championship windows even tighter. While they weigh moving a guard or two and keeping Grant Williams, they have to consider whether they’ll need to completely rebuild the rotation in a few years to accommodate Tatum and Brown’s prime numbers.

Last year, Brad Stevens held most of the rotation together for continuity, then the team spent the season talking about finding their identity and focusing on winning habits. A major injection of talent into the coaching staff could be the solution, but a roster shakeup could be as much about changing this team’s identity as it is about trying to get this core over the hump.

The first domino must not fall on the day of the draw. But it looks like something is coming at some point.

(Top photo by Grant Williams and Derrick White: Winslow Townson/USA Today)

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