The Boston Celtics restructured their books this summer, moving veterans Jrue Holiday and Kristaps Porziņģis to clear up tax savings while Jayson Tatum recovers from his torn Achilles.
In the Holiday move, they added Anfernee Simons, a good young scoring guard who had been sought after to varying degrees over the last year. But with Simons on an expiring contract, word quickly came down from Boston reporters that the Celtics aren’t necessarily committed to Simons short-term, let alone long-term.
So, with Boston still looking to move Simons for better flexibility or roster upgrades, what are some potential deals? Here’s a look at five options.
Note: These trade ideas are speculative and should NOT be used in place of actual reported intel on trade concepts.
Trade 1: Sensible business (Detroit Pistons)
Celtics get: Tobias Harris, 2028 Lottery-protected first-round pick
Detroit Pistons get: Anfernee Simons
Tobias Harris and a lottery-protected first-rounder gets the Pistons a long-term guard addition to use either off the bench or in three-guard lineups with Cade Cunningham and Jaden Ivey. The Pistons surrender at worst a back-15 pick and move Harris’ money for a younger, more long-term investment.
Simons went for Holiday (after second-round compensation was later redacted), so the Pistons are giving up more value here than the Blazers did. But in doing so, they lock in shooting to replace Malik Beasley, and it gives them leverage in Jaden Ivey negotiations. At worst, it’s an expiring contract they can once again flip at the deadline.
The key is that Simons, on a short or long-term deal, has more value than the lottery-protected pick in 2028 and Harris.
For Boston, they add a pick asset, save $200k on their books this season, add a veteran who can help them compete right now, and a good locker room vet who might re-sign for less when they gear up for next season.
Who’s More Mad: Pistons fans. Giving up a first-rounder for a player that went for Jrue Holiday would provide outrage, but the Pistons should value Simons more than Boston did or Portland valued Holiday.
Trade 2: The Cam Gamble (Brooklyn Nets)
Boston Celtics get: Cam Thomas (sign-and-trade, terms negotiable under $27.6 million AAV)
Brooklyn Nets get: Anfenee Simons
The Nets are currently squeezing the financial life out of Thomas, as every team is with their restricted free agents who aren’t max players under the new CBA.
The Celtics can help negotiate for a shorter-term deal for less than Simons. You turn Holiday into a smaller expiring contract, then Simons into a smaller short-term contract with more upside. (Let’s imagine two years, $40 million, player option for next season to enter the 2026 free agency splurge.)
The surprising part? Cam Thomas, who rightfully has been pilloried for being empty calories by ESPN’s Zach Lowe, is still more impactful and useful than Simons, at least by last season’s numbers:
The Celtics acquire a better asset (a younger player with another season), the Nets address their Cam Thomas issue, and can kick the can down the road for another year with Simons. Alternatively, if they believe in him more than Thomas, they can ink him to an extension.
“We don’t really want this guy.”
“We don’t really want THIS guy.”
“Let’s swap.”
“Bet.”
Who’s More Mad: Nets fans, because a. they traded with Boston again, and b. didn’t just get Thomas back on a cheaper, several-seasons deal.
Trade 3: Big Vooch and Big Cap Space (Chicago Bulls)
Boston Celtics get: Nikola Vucevic, Ayo Dosunmu
Chicago Bulls get: Anfernee Simons, Xavier Tillman
The Bulls have a logjam of guards, so adding Simons is a little curious. But think of this way. In adding Simons, they can leverage him against Coby White, who is also on an expiring deal. The player who comes out on top gets extended.
That, along with the Giddey extension, sets their direction for the long-term in the backcourt while Matas Buzelis develops.
The Bulls move off Vucevic while getting value.
The Celtics shave off another $1.4 million off their cap space, while continuing to clean the books for 2026, and add a dogged defender in Dosunmu who fits their system better than Simons. Think of what Dosunmu will learn as Derrick White’s understudy.
Boston adds a legit stretch-five so they aren’t entering the season with nothing, and this greatly improves their chances of making the playoffs this year to then build on it with Tatum, especially if they can get Vooch back at a decreased number.
Who’s More Mad: Bulls fans (you’re noticing a trend here, right) because they either like Ayo, Coby White, or both, and this move decreases both players’ long-term futures with Chicago.
Trade 4: The Herro Ball Play (Heat-Kings 3-Way)
Boston Celtics get: Tyler Herro
Miami Heat get: DeMar DeRozan, Sam Hauser, negotiable draft pick compensation
Sacramento Kings get: Anfernee Simons
Miami ducks the Tyler Herro extension to add DeRozan as a forward playmaker star, aiming for a full reset next season when he’s expiring or the year after. They pick up shooting with Hauser as kind of a fill-in for the shooters they had in 2023 (Gabe Vincent, Max Strus, etc.).
If you want to say Miami needs to get a (heavily protected) first here, I’m fine with that. Herro was legitimately Miami’s best player last season, but that statement is also part of why they were a play-in team that got obliterated by Cleveland.
The Kings move off DeRozan and add Simons. Is Schröder-Simons-LaVine too much? Probably, they’ll have to move LaVine sooner than later, but they can run three guard lineups in the meantime with an amazing amount of shooting. They can commit long-term to Simons on a deal less than LaVine. It’s a pivot.
The Celtics take on Herro who gives them the best player in the trade. He’s an expiring, which is complicated. He plays the same position as White, which is complicated. He arguably plays the same position as Brown, which is complicated. But it’s turning Jrue Holiday into Tyler Herro, which is pretty great, and Herro would absolutely roast in that system.
Who’s Most Mad: Everyone. Everyone is mad here. I suggested this trade, and even I think it would be infuriating. This is an example of how difficult it is to find fits for Simons, DeRozan, and Herro. The money being added to Boston and Miami is just icing on the cake.
Trade 5: The Makkanen Approach (Utah Jazz)
Boston Celtics get: Lauri Markkanen
Utah Jazz get: Anfernee Simons, Sam Hauser, Georges Niang, Xavier Tillman, 2027 1st-round pick swap (top-10 protected), 2030 1st-round pick (top three-protected)
Utah cashes in on Markkanen as they continue their rebuild. They have Ace Bailey and Isaiah Collier, which could be a great young core. You’ve already infuriated Bailey by drafting him where he didn’t want to go, now you can add to it by making him come off the bench.
But seriously, providing Bailey with competition both provides a backup plan and exerts leverage over Bailey to make sure he lives up to his potential. You can start him and Bailey for a ton of scoring potential and bring Collier in as the game manager point guard in the second unit.
The other contracts are valuable for Utah; Tillman is a serviceable backup center, Niang is an expiring contract at eight figures, and Hauser is a pure shooter.
The pick assets are flexible here. This gives the Celtics a long-term, more available Porziņģis replacement. It messes with their cap-saving approach, but just a little, and puts them back into contention in the East even before Tatum gets back.
Who’s More Mad: Jazz fans, giving up their best player to the Ainges’ former team for weak draft capital and expiring contracts without a blue-chipper.