Trail Blazers Trade Anfernee Simons to Celtics for Jrue Holiday

The Trail Blazers are solidifying their identity around a defensive minded approach by acquiring Jrue Holiday.

Full trade first reported by ESPN’s Shams Charania:

“The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second picks.”

Jake Fischer first reported the second round pick compensation: “The Celtics are getting a 2030 Knicks second round pick and a 2031 Blazers second round pick.”

Anfernee Simons was last player left on the roster that was drafted by former Trail Blazer general manager Neil Olshey. The final domino falls- This is now officially the era of Joe Cronin.

League sources have confirmed that the Trail Blazers plan to keep Jrue Holiday and he will not be rerouted. From what I have heard, the Blazers view Holiday as a huge upgrade talent wise and believe him to fit the mold of their identity going forward.

There are two very different perspectives looking at this trade. The initial reaction I had was warped by confusion and the overall shock of this trade happening randomly on a Monday evening. Portland is trading unequivocally their best offensive player. Losing Anfernee Simons means the Blazers are taking a huge hit as far as shot creation and 3pt making- he commanded so much defensive attention from opposing teams because of the sheer gravity of his offense presence.

On top of losing the focal point of their offense, the financial side of things looks pretty bleak. Jrue Holiday is 35 years old and on an ascending contract. $30 million, $32.4M, $34.8M, $37.2M (PLAYER, 2027). Portland will be paying 38 year old Jrue Holiday $37 million. The Trail Blazers were in a position to have north of $50 million in 2026 cap space before the Jrue Holiday trade, and IF they extend Shaedon Sharpe. Now they’re likely to make another trade involving one if not both of their larger earners in Jerami Grant or Deandre Ayton (who’s contract is expiring), but that is a conversation for another day.

The negative aspects of this trade are substantial. Anfernee Simons was the longest tenured player on the roster and is widely considered to be a fan favorite by a lot of Blazers fans. There is no doubt he will be missed.

Now let’s take a look why Joe Cronin and the Blazers did this trade…

Jrue Holiday undoubtedly fills out all the boxes for the players Joe Cronin has built the roster around- High-IQ, defensive minded players. While there are very valid concerns about his age and salary, Holiday provides elite defense from the guard position at every level. He is a player who is comfortable spacing the floor, elite playmaker, and is a smart and crafty organizer- someone who you can trust to run the offense.

Addressing the concerns of what the Blazers offense is going to look like with the departure of Anfernee Simons, I am operating under the belief that the Trail Blazers view forward Deni Avdija to take that role. Avdija finished the season showing that he was more than capable of having a heliocentric offense revolve around him, averaging 17.7 ppg, 7.3 rpg, and 3.6 apg on 50/35/78 splits. Now if we are looking at things from the lenses that Deni is the focal point of the offense moving forward then I start to understand why a player like Jrue Holiday is so attractive.

Jrue Holiday put up career lows in usage rate and 3pt% in Boston last year. Now obviously seeing the 35% from 3 is concerning, but what I am really interested in is how his usage rate has consistently dropped since arriving in Boston. Jrue did not need to be a ball dominate guard to remain effective - he was a stabilizing force offensively for Jalen Brown and Jayson Tatum. He knew when to take their ball out their hands and get them into more favorable spots, especially from 3 point range. I think this skillset is especially appealing when you’re operating under the assumption that the offense is going turned over to Deni Avdija and developing young point guard Scoot Henderson. A savvy veteran with incredibly high IQ and feel for the game will completely change the trajectory for a lot of Portland’s young players.

Let’s look at the fact that Jrue Holiday provides a huge presence in the locker room into consideration. 2 time NBA champion with Milwaukee and Boston, 6 time NBA All Defense Team, and has won the Teammate of the Year award 3 times. His accolades speak for themselves. The Trail Blazers get a mentor, leader, and an outright winner in Jrue Holiday.

Now coupling that with the fact Jrue Holiday is massive upgrade on the defensive end compared to Anfernee Simons, the picture of what the Trail Blazers are trying to do starts to become more clear.

Going back to last years deadline, there was a comment that the Trail Blazers “want to be like the Houston Rockets” was perceived to be negative at the time. We just saw the Houston Rockets finish their season 2nd in the Western Conference with 52-30 record with a defensive minded coach and roster construction. It is evident that this ideology is something the Trail Blazers are building towards. Houston had a myriad of young talent and brought in veterans with bigger contracts in Fred Van Vleet and Dillon Brooks before taking their huge leap- so its not inconceivable to think that Portland is following this playbook coming off a season where they pushed for the play-in and ultimately fell short.

It seems to be that the figuring things out stage of the rebuild is over and the Trail Blazers are positioning themselves to start becoming competitive again. I don’t view this move to be the piece that pushes the Trail Blazers into the championship conversation at all, they are still very far away from that. The draft is on Wednesday and Portland currently holds the 11th pick. I would imagine the Trail Blazers are far from done with making moves. Stay ready for an exciting week.