Jrue Holiday trade grades: Celtics address issues with Anfernee Simons, while more questions for Trail Blazers

The Boston Celtics are trading Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks in the first major trade since the end of the NBA Finals. It’s a fairly rare trade in that the recent champion Celtics are giving away the well-known veteran while the younger rebuilding team is giving away young talent in a win-now effort.

So what does the deal mean? And who won the deal? Let’s grade both Boston’s and Portland’s performance in Monday’s surprise blockbuster.

Boston Celtics: A

Let’s start with a fairly basic question: how good is Jrue Holiday, still? Next year will be his age-35 season. He just averaged 11.1 points per game, his fewest since his rookie year, and he did that in Boston, with nearly perfect spacing to make his life easier. It was the first season he missed out on an All-Defense selection since he left New Orleans in 2020. While he remains an effective defender, he is probably best-suited to guarding wings at this point. Asking him to keep up with the quickest guards in the NBA today is probably a tall order, and that’s going to get harder as he ages.

So Holiday is probably still a helpful, potentially even starting-caliber player that is visibly declining. He is getting paid, however, at nearly a star rate. He will make $32.4 million in his age-35 season, $34.8 million in his age-36 season, and, through a player option, $37.2 million in his age-37 season. Unless you think Holiday is still something close to peak Holiday, that is a negative value contract. It is the sort of deal that a team should probably have to attach money to get off of in a vacuum.

Instead, at the very least, the Celtics get two second-round picks and escape the last two years of Holiday’s contract. Simons is on an expiring $27.7 million contract next season. If they so choose, they can just let him walk. If they do so, they will have gotten two second-round picks, saved roughly $5 million towards their goal of getting below the second apron this season (they’re now around $18 million away) and chopped the last two years of Holiday money off of their books without having given up anything of long-term value to them. That alone is a major win.

But that’s the worst-case outcome for Boston. Anfernee Simons is a good player! He’s averaged 20.7 points per game since becoming a full-time starter three seasons ago, and he’s done that, as Joe Mazzulla surely knows, largely by shooting 37.4% on 8.8 3-point attempts per game. The Celtics love gunners, and Simons is emphatically a gunner. He can create a bit off of the dribble and has grown into an acceptable enough playmaker. With Jayson Tatum sidelined, the Celtics could use this sort of offensive punch if they hope to remain competitive next season.

And Simons is only 26! He might have room to grow. He is, quite frankly, a terrible defensive player, and that’s part of what compelled Portland to trade him, but the Celtics of the Tatum-Jaylen Brown era have been strong enough on that end of the floor to protect him. Even if they can’t, he could still be a high-end sixth man as a vulnerable defender. We’ve only ever seen him carry bad offenses. Now we get to see what he can be in a good one. So at worst the Celtics get sorely needed cap relief. At best, they get a really promising young player who could help them not only while Tatum is out, but after he returns and into the next era of Celtics basketball. Not a bad haul for a contract they were desperate to move.

Portland Trail Blazers: C-

Ok, let’s take the charitable stance here and begin by trying to decipher Portland’s motivation here. If you squint, you can at least get an impression of why they might be interested in Holiday specifically:

• Portland was better than you think down the stretch. They went 13-14 after the All-Star break with the No. 4 defense in the NBA. The Blazers are not contenders, but they are not tankers either.
• They used the No. 7 overall pick in 2022 on Shaedon Sharpe and the No. 3 overall pick in 2023 on Scoot Henderson. Neither has been able to get the offensive usage they’ve needed with Simons gobbling up possessions. Sharpe is extension-eligible. Henderson will be in a year. The Blazers have to find out, once and for all, what they have in these young guards and whether this is a viable long-term foundation. Now, the offense belongs entirely to them. Holiday may be listed as a guard, but again, he’s probably best defending forwards now. If he’s the starting small forward or even comes off of the bench (which, with Deni Avdija and Toumani Camara in place, he likely should), he won’t take anything off the table even with two other guards next to him.
• Jrue Holiday is a revered teammate. He is the only player to win the Twyman-Stokes Teammate of the Year award three times. He’s won the NBA’s Sportsmanship Award twice, and he was just named the Kareem Abdul-Jabbar Social Justice Champion of the 2024-25 NBA season. He is one of the NBA’s great humans, the absolute perfect mentor for a younger locker room. Think of who just won the championship. How did Shai Gilgeous-Alexander’s Oklahoma City experience begin? Alongside Chris Paul. Portland is probably hoping Holiday rubs off on Henderson and Sharpe in the same way.

All of that can be true. These are potentially reasonable motivations. But these were relatively modest goals that could have been accomplished at a far lower price. You can find good locker room veterans without committing three years and $104 million to a once-injury prone player in his ages-35-37 seasons. Just sign Garrett Temple for the minimum. Their head coach is Chauncey Billups. They should be set when it comes to mentorship from legendary guards.

How much better does Holiday make the Blazers? Probably less than they think. Their offense still ranked 20th even in their post-All-Star break surge, and that was with Simons in place. They’ve taken a step backwards in terms of both creation and shooting here, and those weren’t areas Portland was really equipped to step back. Portland ranked 17th in 3-point attempt rate and 26th in 3-point percentage last season. Holiday has been an up-and-down shooter for his entire career, and last year, he dipped below league average from deep. 

Defensively, despite inevitable age-related decline, he’s still good and switchable. If Portland puts him, Avdija and Camara on the floor together, they’ll be able to do a bunch of switching and generate significant ball-pressure. The defense is going to be good. But it was already good. Now think about the Western Conference as a whole.

The Thunder aren’t going anywhere. The Rockets just traded for Kevin Durant. The Lakers are going to get a center. The Warriors have room to improve. The Clippers just had a major bounce-back season. Nikola Jokić still resides in Denver. The Timberwolves made back-to-back Western Conference finals. And if all that’s not enough, Victor Wembanyama is looming. These things are never quite as simple as listing out the rosters in a given conference from most talented to least. Injuries happen. Unexpected calamities ruin seasons. But on paper, the Blazers are … probably a play-in team? And even then they’re competing with teams like Dallas, Memphis and Sacramento. It’s no given that they even sneak into the top 10.

So the actual upside here seems pretty limited. The downside, though? That’s much more severe. First of all, the Blazers had pathways to around $50 million in 2026 cap space. That’s now gone. Holiday occupies most of that space. Second, Portland already owed too much money to one declining, veteran wing in Jerami Grant. Now, they have another in Holiday, and together, they present some meaningful financial issues moving forward.

Now, in the 2027-28 campaign, they are on the hook for over $73 million in combined salary to Holiday in his age-37 season and Grant in his age-33 season. Does that sound optimal for a young team ostensibly built around youth? Remember, Sharpe is extension-eligible now and Henderson will be in a year. In the best-case scenario in which both of them break out and get hefty extensions, those Holiday and Grant contracts make it harder to build around them unless they can be used as expiring deals in trades. With Camara also due a new contract in either the summer of 2026 or 2027, Portland could get shockingly expensive in the near future.

Speaking of Grant, we should probably just touch on the way Portland tends to operate with its veterans. The Blazers have developed a dangerous habit in the Joe Cronin era of holding onto them too long. Damian Lillard is a textbook example. The whole world knew Portland should’ve moved him in 2021. Portland waited two extra years and got less as a result. Last offseason, The Athletic’s Jovan Buha reported that Portland wanted two first-round picks in a possible Grant trade. Now, he’s on a pretty negative contract. 

Had Simons been moved, say, a year ago, when it became clear that Henderson and Sharpe needed minutes and shots, they likely could have walked away with a first-round pick or two. His acquiring team would have gotten a younger version of him with more attached team control. You’re telling me that wouldn’t have appealed to Orlando, who just gave up four first-round picks to Desmond Bane in a similar role? But Portland consistently acts too late when it comes to moving veterans, and they almost always wind up paying the price for it.

That doesn’t mean this can’t be a successful trade. There’s frankly no price the Blazers wouldn’t or shouldn’t pay to turn Henderson and Sharpe into the stars they hope they can be. If Holiday winds up helping get them there? This trade is still a win. But we’ll never quite know if they got there because of Holiday of if they were just ready to break out in bigger roles. We do know how dangerous expensive, long-term contracts like this can be in the apron era. So, all things considered, Portland almost certainly overpaid to accomplish its goals.