Bill Sy: We’re less than a month away from the NBA Draft and the offseason. The rumor mill has been churning with trade targets like Peyton Watson and Trey Murphy III heading to Boston to Jaylen Brown being part of a Giannis Antetokounmpo deal. There hasn’t been any indication that the Celtics front office is ready for a big swing, but Brad Stevens could still make substantial changes to the championship core of the roster. If the Jays are untouchable, that could mean dealing Sam Hauser, Payton Pritchard,
or even Derrick White. Unfortunately, White might be our biggest chip to play.
Nirav Barman: Derrick is currently the third highest paid player on the roster, taking in a whopping $30.3 million next season, but he’s been pivotal to Boston’s success since joining the team. The Celtics have been in the Finals twice since acquiring White, winning the championship in 2024, and were a Tatum ankle-sprain away from what could have been a third trip in 2023. Derrick has blossomed in Boston, and it becomes hard to see him anywhere else purely off of his relationship with the team and the city.
Bill Sy: Don’t get me wrong. I’m a huge DWhite guy and I’ll always be a huge DWhite guy. Despite his shooting struggles this season, I have no doubt that that was just a blip and he’ll make a big comeback next season. However, with two maxed Jays and roster that could use some rebalancing before the front office makes a big push in 2027, White’s salary slot could better be used elsewhere.
Nirav Barman: There’s no question that the Celtics are heading towards crunch time for this core given how hard it’s become to navigate the luxury tax and salary aprons. That being said, there are few players who are both available on the trade market, and possess the skill set which White does. Even if you’re looking to address another area of concern for the team in exchange for Derrick, it’s hard to see the team acquiring a player who provides the same value on a similar deal.
Bill Sy: For a minute, let’s put aside who’s available on the market and concentrate who’s already on the team. A big part of my confidence in even considering trading White was the development and performance of all the young wings in Boston’s bullpen: Hugo Gonzalez, Baylor Scheierman, Jordan Walsh, and Ron Harper Jr. Admittedly, you can’t play all those guys at the same time, but I think you can create Derrick’s contributions in the aggregate just as OKC did with Ajay Mitchell, Jared McCain, and Cason Wallace in replacing Jalen Williams.
Nirav Barman: I’m extremely excited to see what our group of young guys can do next season after what they just showed us, but I don’t think they’ve showed us enough to make White expendable just yet. As you said, their current skill sets need to be aggregated to make up for Derrick’s impact. When a game reaches clutch time, you need to have your best five players on the court, and those moments are where Derrick shines the most. JB and JT are guaranteed spots in a closing lineup. If we presume White is traded for a big man, that means there are two spots left between Pritchard and the wings. It’s hard for just one of those guys to fill that role and feel like we’re putting out a better lineup.
Bill Sy: Let’s zoom out a little bit. If we’re going to take Stevens at his word, he’s looking to add rim pressure this summer. Brown led the league in drives per game last season at 19.1. Payton Pritchard trailed behind at 11.9 and in his limited return, Tatum drove to the basket 10.9 times. White? 7.5.
Nirav Barman: It’s true that Derrick doesn’t quite play the way Stevens envisions for the future. However, he’s proven before that he can fit different systems. White fully embraced Mazzulla-ball after joining the Celtics, bumping his 3PA average up from 3.7 per game across 4.5 seasons in San Antonio to 7.0 per game across 4.5 seasons in Boston. There’s no reason why White can’t adjust his shot diet again if the team is looking to drive the ball more.
Bill Sy: The bigger question for me is whether White can be more of an alpha that can make the game a little easier for Brown and Tatum (think Holiday circa 2024) or if he’s the best supporting role player.
Nirav Barman: To your point, I wouldn’t call White an alpha. As great as he is, he doesn’t have the ability to take over games on a consistent basis. That being said, there are only so many slices of the pie available, and it already feels like the world has been trying to drive a wedge between Tatum and Brown because they’re both alphas. Having a high-level supporting role player like Derrick seems to me like the best path to success with the Jays as the foundation.
Bill Sy: Unlike the Knicks, because we have two max players, we have to be really deliberate with roster construction. And don’t get me wrong. The thought of trading an All-Defense First Teamer from a team with championship aspirations seems silly, but I’m just wondering if we’re not in the same spot we were in with Marcus Smart. At the time, the approach was to surround the Jays with more senior, more proven veterans like Holiday and Porzingis. Now, I’m wondering if we go younger with the Jays in their prime. Could this be those crossroads?
Nirav Barman: It does feel like we’re reaching a point where we’re going to have to make some tough decisions again. The Celtics simply have to improve the roster to keep up with the rest of the top teams. I do think that there are paths to do that which don’t require trading Derrick, though – at least as of now. Boston has a $27.7M TPE from offloading Anfernee Simons, and while they’d have to include some assets to get a good player back, it gives the team a lot more flexibility to address areas of concern while keeping White and allowing the cream of the crop to rise to the top from the selection of young wings. (edited)
Bill Sy: Depending on a handful of team options, the Celtics are projected to enter free agency with a $180-185 million payroll and their first round pick is ticketed for $3 million. Stevens will have the $15 million non-taxpayer mid-level exception and that $27 million TPE at his disposal, but ultimately, they’re most likely going to try and duck under the luxury tax line at $201 million again to restart the repeater. So, in reality, they’ve got about $15-20 million in wiggle room. White’s $30 million slot might need to be in play.
Nirav Barman: Even while toeing the luxury tax line, Boston can’t let money override their on-court success. If the right deal comes around, I definitely think trading Derrick can and should be on the table – he’s well loved, but certainly not untouchable. If the expectation is that the young guys will fill in for him, though, it hasn’t quite gotten to that point yet. Until proven otherwise, which could happen by the trade deadline, Derrick gives the Celtics the best chance at staying competitive.
Bill Sy: I guess my thinking is that White’s $30 million and that $15-20 million are the best tools to makeover the roster. Here’s a very hypothetical trade: let’s say Stevens strikes a sign-and-trade deal with Danny Ainge with Walker Kessler going east and White joining Utah’s backcourt. Then, with the MLE, Coby White replaces Derrick White as Boston’s rim-pressuring point guard. Mazzulla would roll out a rotation of:
- Coby White – Sam Hauser – Jaylen Brown – Jayson Tatum – Walker Kessler
- Payton Pritchard – Baylor Scheierman – Hugo Gonzalez – Jordan Walsh – Neemias Queta
- Ron Harper Jr. – 27th pick – Amari Williams – Luka Garza
Rebalancing the front court and back court with younger players sets them up for the immediate and long-term future.
Nirav Barman: I definitely see the appeal in a trade like that. As you pointed out earlier, Brad Stevens isn’t opposed to swapping a fan favorite for someone with clear potential that’s been stuck on a bad team. I’m sure he’ll be doing his due diligence, but I would find it difficult to make a deal predicated on a potential signing since it could create a bigger void if Boston gets outbid. As of now, the free agent market is pretty sparse for both the Celtics areas of need, PGs and Cs. If the Celtics are able to comfortably address one of those needs, then a Derrick trade could become more viable.
Bill Sy: I will admit after seeing OG Anunoby tip in the Jalen Brunson miss, the first thing I thought about was DWhite rebounding Smart’s miss and forcing a Game 7 against the Heat. Who would want to trade a guy like that?
