Celtics’ Jrue Holiday return loses its luster after Blazers alter trade

The Boston Celtics 2025-26 season ended before it started. Jayson Tatum tearing his achillies, likely puts him out for all next season. With the Celtics being well above the second apron, they needed to clear cap space to avoid paying the high tax that comes with it.

The first move they made was trading Jrue Holiday. They sent him to the Portland Trail Blazers for guard Anfernee Simons and two future second round picks. Due to Holiday's medical history, the trade has been altered, in a straight player-for-player swap, with no picks.

Although the premises of the trade remains intact, by clearing cap space and getting a younger scorer in return for an aging star, the loss of the two picks causes the luster of this trade to dissipate on Boston's side.

Should Celtics fans be worried?

Although having two extra picks to potentially shop around, it's not that instrumental to what the Celtics are trying to do. The fact that Holiday's medical history is in question and they were able to move on from it without the whole trade being rescinded is a plus.

Simons has averaged 20.7 points per game over the last three seasons, taking 8.8 3-pointers a game while shooting 37.4 percent. He's averaged 4.7 assists as well. The way Boston head coach Joe Mazzulla coaches, Simons is the perfect player for his system.

As currently constructed and the way the Eastern Conference is laid out, the Celtics will likely make the playoffs. Derrick White is going to have a bigger role, which he will find success in, and the added play from Simons will help White and Jaylen Brown carry the load.

The Celtics still are on the winning side of the trade, even without the extra picks. They cleared up the necessary cap space and got rid of an aging player for someone who is much younger and more adept to Boston's system. In this new system, the Celtics will find success, just not the success fans have been accustomed too since 2017, where they've been a lock to make the conference finals.