I have a lot of thoughts on the late Monday trade of Jrue Holiday to Portland for Anfernee Simons and two second-round picks, because it wasn’t really something I expected.
The Blazers are a young team that is possibly on the rise but doesn’t necessarily need to be paying a 37-year-old $37 million three years from now … especially when they’re already committed to paying Jerami Grant $36 million the same season. One wonders how they’ll have any money left over to pay the players who are actually central to their plans. On the flip side, Simons makes nearly as much as Holiday in 2025-26 and doesn’t advance the ball that much in terms of digging the Celtics out of their second-apron hole.
Let’s start with Boston, though, because this was another tremendous swap by a front office that has won nearly every trade for the last half decade.
The most amazing thing about this trade is that the Celtics got off the final two years of Holiday’s deal while receiving draft picks instead of sending them out. The three years and $104.4 million left on Holiday’s deal projected to be deeply underwater value-wise; I wondered whether the Celtics would have to give up two firsts to move off his money or whether they could get away with one.
While Holiday is still a plus defender and an A-plus in the locker room, my BORD$ formula valued him at $19 million for the coming season – nearly identical to how it rated Simons – and he’s making nearly double that. Presumably, his age-36 and age-37 seasons in the two years after would project worse, but Holiday’s salary rises in those years.
Setting aside what Simons can do on the court, the sheer value of dropping the final two years of that contract for Boston is massive. Simons, however, is a real basketball player who is on an expiring contract that pays him $27.7 million this coming season.
Boston could theoretically extend Simons’ deal, but that would only make sense if the Celtics were moving another big contract this summer. Otherwise, the next move for the Celtics might be to keep whittling down their cap number in a series of subsequent trades. Imagine, for instance, Boston flipping Simons to Sacramento for Malik Monk and Devin Carter, then flipping Monk to Dallas for P.J. Washington, then flipping Washington into a team’s nontaxpayer midlevel exception for a draft pick.
I’m not saying any of those trades are likely or even being discussed, but I am giving you an example of how the Celtics can stairstep down from Simons’ $27.7 million, to a combined $23.7 million for Monk and Carter, to $14.1 million for Washington and $4.9 million for Carter, to just holding Carter’s rookie contract for $4.9 million and being under the second apron. There are infinite pathways to doing something like this; also, it’s possible the last step can be done in-season.
One way or another, however, the Celtics are nowhere close to done, because the incentives for them to reduce their luxury-tax penalty (including a punitive repeater tax) and unfreeze their 2032 draft pick (by staying below the second apron three times in the next four years) are overwhelming in a “gap year” where Jayson Tatum will miss the season recovering from a torn Achilles.
As for Portland, I’m baffled. Between the recent contract extensions for GM Joe Cronin and coach Chauncey Billups and the fact that the team is for sale, it seemed like Blazers management was in a great situation to take the long view and spend one more year hunting young talent and developing players. They could push to move up in the fiercely competitive West once Deandre Ayton’s $35.5 million salary was off their books and their younger players had another year of experience.
The Blazers improved over the second half of last season, but this was a 36-win team that relied on Simons to create half-court offense on a squad with little dependable shooting and playmaking. The point guard reins are now seemingly turned over to 21-year-old Scoot Henderson, but his first two seasons have been a struggle.
The one plus for Portland is that even the Holiday and Grant contracts might not push their salary structure past the breaking point because of the value that is the next three years of Deni Avdija’s declining-money contract; Donovan Clingan will also still be on his rookie contact in the last year of the Holiday and Grant deals.
Let’s wait and see what else the Blazers cook up this offseason; maybe they can wave a magic wand and turn Ayton into a point guard and a shooter. At this moment, however, I am flabbergasted that they sent out draft capital to turn Simons into Holiday. Even if you think Holiday is the better short-term fit, the nine-year age difference on a team that is not exactly contention-ready is a major minus for the out years, and they got nothing else back for their trouble. I don’t get it.
