The Boston Celtics are moving Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round selections, the first significant move since the NBA Finals. It’s a rather unusual trade in that the recent champion Boston Celtics are sending away a well-known veteran while the younger rebuilding team is giving away young players in a win-now effort.
So, what does the arrangement entail? Who won the deal? Let’s evaluate both Boston and Portland’s performances in Monday’s surprise blockbuster.
Boston Celtics: A
Let’s start with a straightforward question: how good is Jrue Holiday still? Next year will be his 35th season. He only averaged 11.1 points per game, his lowest since his rookie year, and he did so in Boston, with nearly perfect space to make his job more manageable. It was the first time he had missed out on an All-Defense selection since leaving New Orleans in 2020. While he remains an effective defender, he is perhaps best suited to protecting wings at this point. Asking him to keep up with the NBA’s quickest guards now is a huge order, and it will become more difficult as he grows.
So Holiday is likely still a helpful, possibly even starting-calibre guy who is visibly deteriorating. He is, nevertheless, being compensated at virtually a star rate. He will earn $32.4 million in his 35th season, $34.8 million in his 36th season, and $37.2 million in his 37th season, thanks to a player option. Unless you believe Holiday is still at its top, that is a contract with a negative value. In a vacuum, it is the type of transaction to which a team should have to attach money to exit.
Instead, the Boston Celtics receive two second-round picks and avoid having to pay Holiday’s final two years’ salary. Simons’ $27.7 million contract expires next season. If they so desire, they can just let him walk. If they do so, they will have received two second-round picks, saved approximately $5 million toward their goal of falling below the second apron this season (they are now about $18 million away), and removed the last two years of Holiday money from their books without giving up anything of long-term value to them. That alone is a significant victory.
But it is the worst-case scenario for Boston Celtics. Anfernee Simons is a skilled player! Since becoming a full-time starter three seasons ago, he has averaged 20.7 points per game, thanks in large part to a 37.4% shooting percentage on 8.8 3-point attempts a game. The Boston Celtics adore gunners, and Simons is undoubtedly one. He can produce a little off the dribble and has become an acceptable playmaker. With Jayson Tatum out, the Celtics could use this type of offensive punch if they want to stay competitive next season.
And Simons is only 26! He might have room to grow. He is, quite honestly, a dreadful defensive player, which is one of the reasons Portland traded him, but the Boston Celtics of the Tatum-Jaylen Brown era have been good enough on that end of the court to protect him. Even if they can’t, he may make an excellent sixth man as a susceptible defender. We’ve only seen him commit alarming offences. Now we can see what he can do in a good one. So, at worst, the Celtics receive much-needed cap relief.
At best, they get an up-and-coming young player who can help them not only while Tatum is out but also when he returns and ushers in the next era of Boston Celtics basketball. Not a bad deal for a contract they needed to relocate.
Portland Trail Blazers: C-.
Okay, let’s take a compassionate approach and try to figure out Portland’s motivations here. If you squint, you can get an impression of why they might be particularly interested in Holiday:
- Portland performed better than expected down the stretch. They finished 13-14 after the All-Star break, with the NBA’s fourth-best defense. The Blazers are not competitors, nor are they tankers.
- They drafted Shaedon Sharpe with the seventh overall pick in 2022 and Scoot Henderson with the third overall pick in 2023. Neither has been able to acquire the offensive use they require, with Simons hogging possessions. Sharpe is eligible for an extension. Henderson will be in a year. The Blazers must determine, once and for all, what they have in these young guards and whether this is a sustainable basis. They now fully bear responsibility for the offence.
- Jrue Holiday is a well-regarded teammate. He is the only player to have received the Twyman-Stokes Teammate of the Year award three times. He has twice earned the NBA Sportsmanship Award and was just awarded the Kareem Abdul-Jabbar Social Justice Champion for the 2024-25 season. He is one of the NBA’s greatest human beings and the ideal mentor for a younger locker room. Think about who just won the title. How did Shai Gilgeous-Alexander’s Oklahoma City journey begin? Alongside Chris Paul. Portland is undoubtedly hoping that Holiday has a similar effect on Henderson and Sharpe.
All of this could be true. These are theoretically reasonable motivations. However, these were relatively modest aims that could have been met at a significantly lesser cost. You can locate strong locker room veterans without committing three years and $104 million to a once-injured player between the ages of 35 and 37. Simply sign Garrett Temple for the minimum. Their head coach is Chauncey Billups. They should be set for mentorship from famous guards.
How much does Holiday improve the Blazers? Probably less than they realize. Despite their post-All-Star break surge, their offence ranked 20th, and Simons was still in place. They’ve taken a step backwards in terms of both creation and shooting in Portland, and those weren’t areas in which Portland was particularly well-equipped. Last season, Portland placed 17th in 3-point attempts and 26th in 3-point percentage. Holiday has been an up-and-down shooter throughout his career, and last year, he shot below league average-from deep.
Defensively, despite the unavoidable age-related deterioration, he remains good and versatile. If Portland puts him, Avdija, and Camara on the floor together, they’ll be able to switch a lot and generate a lot of ball pressure. The defence is going to be good. But it was already good. Consider the Western Conference as a whole.
The Thunder are not going anywhere. The Rockets recently acquired Kevin Durant in a trade. The Lakers are about to receive a centre. The Warriors have space for improvement. The Clippers recently had a big comeback season. Nikola Jokić still lives in Denver. The Timberwolves advanced to the Western Conference finals in consecutive seasons. And if that wasn’t enough, Victor Wembanyama is on the horizon. These things are never as simple as putting a conference’s rosters in order of talent. Injuries occur.
So, the actual upside here appears to be quite limited. But what about the downside? That’s far more serious. First and foremost, the Blazers had access to almost $50 million in 2026 cap space. That is no longer there. The holiday takes up most of that room. Second, Portland already owed too much money to one fading veteran winger, Jerami Grant. They now have another Holiday, and combined, they present some critical financial difficulties for the future.
Now, in the 2027-28 season, they are obligated to pay almost $73 million in total salary to Holiday at age 37 and Grant at age 33. Does it seem ideal for a young squad ostensibly oriented around youth? Remember that Sharpe is available for an extension right now, whereas Henderson will be in a year. In the best-case scenario, both of them break out and receive significant extensions, but the Holiday and Grant contracts make it difficult to build around them until they can be used as expiring deals in trades. With Camara set to sign a new deal in either the summer of 2026 or 2027, Portland might become astonishingly pricey shortly.
Speaking of Grant, we should certainly discuss how Portland treats its veterans. During the Joe Cronin era, the Blazers acquired a dangerous tendency to cling onto them for too long. Damian Lillard serves as a textbook example. The entire world knew Portland should’ve relocated him in 2021. Portland waited an extra two years and received less as a result. Last offseason, Jovan Buha of The Athletic reported that Portland sought two first-round selections in a prospective Grant trade. He now has a somewhat negative contract.
If Simons had been moved a year earlier, when it became evident that Henderson and Sharpe needed minutes and shoots, they might have walked away with a first-round selection or two. His acquiring team would have received a younger version of him with increased team control. You’re telling me that wouldn’t have appealed to Orlando, who recently traded four first-round choices for Desmond Bane in a similar role? However, Portland repeatedly delays the relocation of veterans, and they nearly always pay the price.
That is not to say that this trade cannot be profitable. There is no price the Blazers would or should not pay to develop Henderson and Sharpe into the stars they aspire to be. What if a Holiday helps them get there? This trade is still a success. But we’ll never know if they got there because of the Holiday or because they were simply ready to break out in larger parts. We understand how risky, pricey, long-term contracts like these might be during the apron era. Overall, Portland very definitely overpaid to achieve its goals.
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