The Boston Celtics performed better than anyone expected in 2025-26. They entered this season with very low expectations as there was no guarantee that top star Jayson Tatum would suit up as he recovered from a torn Achilles suffered the previous spring. However, an MVP-caliber season from Jaylen Brown and a defense that gave up a league-leading 107.2 points per game, earning them the No. 2 seed in the East playoffs.
With Tatum returning in March and immediately looking impressive, the Celtics began the postseason as favorites to reach the NBA Finals. However, despite having a 3–1 series lead over the Philadelphia 76ers, they were surprisingly eliminated in the opening round for the first time since the bubble playoffs.
His exit in the first round raises many questions on the structure of this team. Could they be finals contenders as they try to field two players with supermax contracts? Is making the playoffs every year enough? If the goal is to compete for championships, the Celtics need to make some big changes.
With that in mind, let's take a look at five bold deals the Celtics could make this summer.
Bam Adebayo, Jaime Jaquez Jr. and first-round picks Jaylen Brown in 2028, 2030 and 2032
If the Celtics decide they need to move one of those supermax contracts, Brown will likely be the odd man out, despite being an MVP candidate. But if they ever wanted to trade him, now would be the right time as his value is as high as it will ever be.
If there's any glaring weakness for Boston, it's in the front court. If they trade Brown, they still have strong core talent in Tatum and Derrick White. This is why Miami Heat great Bam Adebayo could be a trade target. He will give them both a defensive force on the front line and a good scorer who will help make up for the points left due to losing the Browns.
A deal that sends Adebayo, Jaime Jaquez Jr. and two future first-round picks should get a deal done.
Jaylen Brown, Malik Monk, two first picks, including lottery selection in June, for Domantas Sabonis
Another potential target to strengthen the front court could be three-time All-Star Domantas Sabonis. While the Sacramento Kings star isn't a defensive force, he is an elite rebounder and can stretch the floor just like Kristaps Porzingis and Al Horford.
To put the money to work, the Celtics would need to pick up the two years and $41 million remaining on Malik Monk's contract. But if they get two first-rounders back in the deal, including the Kings' lottery pick in June, that's fine. The biggest issue is that Sacramento will have to find a trade for Zach LaVine and/or DeMar DeRozan after a deal is made.
Derrick White for Jakob Poeltl and Grady Dick
The Celtics don't need to trade Brown to be better in 2026-27. However, this would mean they would have to move on from fan-favorite defensive player Derrick White. A potential trade could see the two-time All-Defensive Team honoree sent to the Toronto Raptors for centers Jakob Poeltl and Grady Dick.
While it's not a sexy trade on the surface, Poeltl is a rock-solid and strong anchor in the front court that does everything you need to stabilize that position. As for Dick, he could be a potential steal who could be an impact player in Joe Mazzulla's three-point-heavy attack.
Jaylen Brown for Giannis Antetokounmpo
Since Brown had such an impressive season, another option would be a swap for Milwaukee Bucks great Giannis Antetokounmpo. While the Greek icon has more accolades, Brown is a few years younger and far healthier than the 10-time All-Star has been in recent years. If necessary, the Celtics can add a future first-rounder, but they shouldn't add more than that.
The Bucks will get to build a new star in his prime, while the Celtics can experiment with the combo of Antetokounmpo and Tatum for a season. If that doesn't work out, they free up a ton of cap space after next season if he opts out in search of a new long-term deal.
Jaylen Brown for Alpern Sengun, Fred VanVleet and two first-round picks
An interesting young star who could be on the trade block this summer, and who addresses the Celtics' frontcourt needs, is Houston Rockets two-time All-Star Alpern Sengun. While he has been questioned for his play consistently and early in the playoffs, he is still only 23 and has excelled in Ime Udoka's defense-first system.
Houston would be interested in a championship by pairing Jaylen Brown with Kevin Durant in 2026-27. But Sengun and Tatum have plenty of long-term potential. Additionally, to make the money work, the Celtics would get veteran guard Fred VanVleet (if he opts into the final year of his deal) and two future first-round picks.
