Following Jayson Tatum’s injury in the 2025 playoffs, it was clear the Celtics would make serious changes. The team was unwilling to pay the luxury tax to keep their championship roster intact 

This offseason, Boston parted ways with two key starters from their championship team in 2024. That included Jrue Holiday and Kristaps Porzingis. In the trade with Portland for Holiday, the Celtics acquired Anfernee Simons and two second-round picks. Due to issues with Jrue Holiday’s medical records, the Trail Blazers have tweaked the deal. It is now a player-for-player swap between Holiday and Simons. Boston loses the two second-round picks.

The Celtics’ trade for Jrue Holiday looks worse after losing two second-round picks

The Jrue Holiday trade is now official, but the trade will be altered after Portland flagged something in Holiday’s medical, per @AaronJFentress

Instead of Boston getting two second-round picks, it’ll be a straight up swap of Holiday for Anfernee Simons

Tough break for Boston pic.twitter.com/VdFkGobj12

— Celtics Lead (@CelticsLead) July 7, 2025

After the 2024-25 season, Celtics fans knew their team was set to be split up. Without Jayson Tatum in 2025-26, Boston doesn’t have a real chance to compete in the East. That’s why Boston parted ways with two-time NBA champion Jrue Holiday. The 35-year-old just finished his 16th professional season. He started 62 of 82 games for Boston. Holiday was initially traded to the Trail Blazers in exchange for Anfernee Simons and two second-round picks.

Aaron Fentress of The Oregonian reported that an issue with Holiday’s medical record appeared following the trade agreement. This allows Portland to revise what the Celtics will receive. Boston is being stripped of the two second-round picks it received from the Trail Blazers. Instead, the trade is now a straight-up player-for-player swap. Jrue Holiday is with Portland, and Anfernee Simons is with Boston.

The Anfernee Simons-Jrue Holiday trade is now official, without the previously reported second-round picks going from Portland to Boston. The final deal is a straight 1-for-1 player swap. pic.twitter.com/LBNdrT15Co

— Sean Highkin (@highkin) July 7, 2025

Losing the draft capital makes the Jrue Holiday trade a true salary dump for the Celtics. The two-time all-star is owed over $32 million in each of his next three seasons. On the flip side, Simons has one year left on his contract. He’s likely a one-year rental for Boston. Simons started a career-high 70 games for the Trail Blazers in 2024-25.

He averaged 19.3 points, 2.7 rebounds, and 4.8 assists per game. The 2025-26 season is a contract year for Anfernee Simons. He’ll look to play his best basketball to earn a long-term contract elsewhere. Jrue Holiday’s medical record was not enough for the Blazers to rescind the trade, but they were able to take back the two second-round picks.

&nbsp