Who Will Be on the 2027-2028 Celtics? Or, Why The C's Should Probably Trade Derrick White

But first, a quick word on the Conference Finals:

You would think given the fact that only one of the four teams I predicted to make the Conference Finals actually got there that I'd be eager to stick with that prediction. But I'm not. I think the Thunder were lucky to get past the Nuggets. Ahead of round two, I said "The Nuggets are going to be on fumes soon, if they're not already." Somehow, it took until Game 7 for that to be true. It wasn't until then, when Michael Porter Jr. was playing with one arm, and Aaron Gordon was playing on one leg, and Nikola Jokić was clearly exhausted – his nine field goals attempted tied for his career playoff low with his very first career playoff game back in 2019 – that the Thunder pulled away. And even then, it took them until three minutes before halftime and Scott Foster & Co. suddenly swallowing the whistle on a few very obvious fouls that led to steals to do so. Denver didn't want to extend their rotation, and they didn't have good defenders for Shai Gilgeous-Alexander. Minnesota has neither of these problems. Wolves in 7.

The same is true of the Knicks. For all the talk of the Celtics' three-point struggles in the first two games, the Celtics shot .350 from three for the series, and the Knicks shot .351. By the end of the series, Jayson Tatum was out, Jaylen Brown had a meniscus tear in his knee, and Kristaps Porzingis had what Brad Stevens is now calling "post-viral syndrome" – which is the very first time in my life that I've ever heard that phrase. Jrue Holiday dealt with a bum hamstring, and Sam Hauser dealt with a bum ankle. And the Celtics took Game 5 off the Knicks anyway, despite the Knicks being healthy the whole series.

There was also a lot of criticism of the Celtics collectively and Jayson Tatum individually walking the ball up the floor. You know who else walked the ball up the floor? The Knicks. For the series, they each had the same exact 92.0 pace as Boston. 92.0 would have ranked deader than dead last this season, and was much lower than the Knicks' 96.7 pace in the regular season. You know who kept the pace moving in the second round? Why, the Indiana Pacers, of course! They played with a 99.9 pace in the regular season, good for seventh overall, and in the second round against Cleveland consistently got easy buckets because they pushed pace after made baskets. Their pace for the Cleveland series was 100.8. The Eastern Conference Finals will be dictated by who can control pace. Last season, the Pacers allowed the Celtics to dictate pace – both teams played at a slow 95.9 for the series. This year, the Pacers have even more incentive to play at a fast pace, because they run 10 players deep and the Knicks only want to play seven guys, and two of those seven are plodding big men. Pacers in six.

Who Will Be on the 2027-2028 Celtics?

This is the big question. Why is it the big question? Two things are going to line up starting in that season. The first is that it can be the first season the C's really start spending money again. The Celtics want to get out of the luxury tax over the next two seasons to avoid having to continue to pay the repeater tax. The repeater tax, if you're not familiar, is what caused the team's payroll to skyrocket so much this season. Essentially, for every dollar the team was over the luxury tax line, they paid $8.70, which even I believe is unacceptable in any scenario other than "trying to repeat as NBA champion." That was the scenario this season. It won't be in the next two. And you have to be under it for two years in order to wipe the slate clean.

The second thing is that in the 2027-2028 season, Jayson Tatum will be in his second season post-surgery. He's going to miss the 2025-2026 season, and the 2026-2027 will be his first season back. There are plenty of examples of players needing a season to get right before getting back to their dominant selves – Paul George, Klay Thompson, and Jamal Murray come quickly to mind. So I think that makes 2027-2028 the key season. If all goes well, that season's team will be ready to roll on the court, and ready to roll in the board room. Jaylen Brown and Jayson Tatum will be in their final two seasons on the payroll at that point, and JT will have a player option in 2029-2030 that seems likely he'd pick up. So that's a three-year window. That is the next three-year championship window, and the question is how do the Celtics get from here to there.

There will be a lot of painful cuts on the way. If you want to look into the math of it all, Ryan Bernardoni has a much better piece on this than I could ever write, and I urge you to take a look at that. But basically, in order to duck under the luxury tax line the team needs to get rid of at least $45 million in payroll. There was also a decent summary of the team's various potential strategies on The Ringer. (And as long as I'm linking things, there were good pieces on Jayson Tatum's injury in the context of the league as a whole here, and on the team's history here by the great Wright Thompson.)

So if we're looking at a two-year window of austerity – that the 2025-2026 and 2026-2027 teams will not go all out financially to win a title, and the cycle of big spending will start up again in 2027-2028 – the question then becomes who is going to be on the team for that 2027-2028 season? Let's first look at what our salary situation is heading into that season:

There's a lot of players from this current roster who aren't under contract for that season, and there are two – Jrue Holiday and Derrick White who are significantly older than the other players who are. I think it's pretty clear that the Celtics don't want to pay 37-year-old Jrue Holiday $37M. The biggest question I think the Celtics have to answer is whether they believe 33-year-old Derrick White will still be an impact player, and if he will be, if he'll be able to sustain it at ages 34 and 35 as well.

It's a tricky question, and you don't need to look any further than Jrue Holiday to see why. Jrue was 33 last season, and 34 this season. Let's take a look at how his seasons stacked up:

To say there was a precipitous drop in Holiday's production would be an understatement. All season, we told ourselves that this was fine in the regular season, that the team was being careful with Holiday and he would turn it on in the playoffs. And then he missed the final three games of the Orlando series with hamstring problems. He was removed from the injury report vs. the Knicks, but aside from Games 1 and 5, he was pretty bad:

• Game 1: 16 points on 14 FGA, 6 rebounds, 3 assists
• Game 2: 10 points on 6 FGA, 3 rebounds, 5 assists
• Game 3: 8 points on 4 FGA, 2 rebounds, 4 assists
• Game 4: 4 points on 5 FGA, 4 rebounds, 3 assists
• Game 5: 14 points on 8 FGA, 7 rebounds, 3 assists
• Game 6: 4 points on 8 FGA, 4 rebounds, 3 assists

Look back to a year ago in the final three rounds of the playoffs, and you can see stat lines like this:

• Game 3 at CLE: 18 points on 10 FGA, 8 rebounds, 5 assists
• Game 1 vs. IND: 28 points on 16 FGA, 7 rebounds, 8 assists
• Game 2 vs. IND: 15 points on 7 FGA, 4 rebounds, 10 assists
• Game 2 vs. DAL: 26 points on 14 FGA, 11 rebounds, 3 assists
• Game 5 vs. DAL: 15 points on 14 FGA, 11 rebounds, 4 assists

Was Holiday that good in every playoff game last season? No, of course not. But the Celtics didn't need him to be. They needed him to pick his spots and take over when the situation called for it. The situation called for it plenty in this postseason, none more so than Games 2 and 4 vs. New York. And in neither game did he make an impact, particularly Game 4, when he and everyone not named Jayson Tatum disappeared altogether.

Is that what is waiting for the C's in the age-34 season for Derrick White? That's what the team needs to decide. Reflexively, you and I likely want to say that trading Derrick White is ludicrous. That he is the backbone of the team, and one of the most fun Celtics to watch. I know people whose favorite player is Derrick White, who believe that he plays the game the right way. He's not my favorite player, but I agree with everything else. I love Derrick White. He was willing to lose teeth to get the Celtics a championship. I fucking LOVE Derrick White.

And yet, if you're looking at the Celtics' trade assets today, and trying to see not only where you can get the largest draft pick haul and which player would have the most suitors, the answer is very clearly Derrick White. His salary is reasonable, he's a malleable, winning player who does well with the ball in his hands and playing off the ball, he excels defensively in all situations, and he is the right combination of age and experience to be valuable to every single team in the NBA. There's an outside shot he even makes an All-Defense team this season. And again, the goal is not to be good in 2025-2026 and 2026-2027. It's trying to establish a second dominant run with Tatum and Brown starting in 2027-2028. And I think it's fair to question whether D White will be part of that run. And if you can't be 100% sure he'll be part of that next dominant stretch, the best thing to do is trade him at the peak of his value, and he is very much at the peak of his value right now.

The team should be trying to trade Hauser, Holiday and Porzingis first, but as Bernardoni's article and others make clear, that may not be enough to duck enough under the luxury tax. If it is, great! Personally, I don't see it, because I don't think there's any chance the team can trade Porzingis, and even if they do, I doubt they realize much savings from it. Bill Simmons' idea is trading him for John Collins, which would save a grand total of $4,151,707 next year. A drop in the bucket on the way to cutting $45M. But maybe, just maybe, Brad Stevens has several rabbits to pull out of his hat, and he can duck under the luxury tax while still retaining Tatum, Brown, White, and Pritchard. I would love that very much. It's not imperative that everyone be in the exact same age range, and obviously 33, 34, and 35 years old is not too old to win a title. The C's just did so with 33-year-old Jrue Holiday and 37-year-old Al Horford. I just don't think that retaining all four players is likely, and White clearly has the most trade value of the four.

Ultimately, the Celtics now need to build for a three-year window that encompasses the 2027-2028, 2028-2029, and 2029-2030 seasons. The combination of Jayson Tatum, Jaylen Brown, and shrewd front-office management already brought the Celtics a title. I believe with my entire being that it can bring them another. To me, trading either JT or JB is non-negotiable. So if you are at the position that 1) JT and JB have to stay and that 2) the window is 2027-2030, the biggest question becomes whether you keep Derrick White. I think the smartest thing to do, as painful as it will be, will be to trade him now.