The Portland Trail Blazers have traded guard Anfernee Simons to the Boston Celtics for Jrue Holiday. It was one of those rare deals that had no foreshadowing, not a hint of a rumor. Just as Blazers fans were preparing to debate the 11th pick in this week’s 2025 NBA Draft on an otherwise-innocuous Monday night, ESPN’s Shams Charania flew over the Portland metro area like a megalith seagull, dropping the news on unsuspecting the domes of Portland’s faithful.

The surprise accompanying this exchange might be credited to Blazers General Manager Joe Cronin and his front office. Loose lips sink ships. They kept this one afloat until it crashed into the harbor.

Alternately, it might be ascribed to a simpler reality: Who could believe they’d actually do this?

The methodology of NBA trading is classic and time-tested. There are four ways to “win” any deal, a quartet of edges on which to hang your hat when advertising the virtues of a swap. Teams can get more talented, younger, save money, or get future draft capital.

Many trades happen because teams are valuing different qualities. One team gets younger and receives future draft picks, the other gets more talented right now. Rare is the deal where one team takes the “L” in all four categories.

The Blazers may have just executed one.

The big question is whether the Blazers got more talented. Here, beauty is in the eye of the beholder.

Holiday is more experienced, a truer point guard, and a far better defender than Simons. Simons is a superior, more versatile scorer. He’s also a better three-point shooter, a critical area of need for the Blazers. An argument can be made that Holiday is a deep threat; his career average and past performances are significantly better than the 35.3% clip he fired last season. That’s also true of Simons, though. It’s at least fair to say the Blazers did not get better in this critical category. They may have gotten worse.

Holiday’s defensive acumen does fit with the team profile better than Simons did. But Portland’s defense was decent last season. Their offense was impoverished. They didn’t help themselves there.

Holiday is a point guard. Simons wasn’t. But the Blazers supposedly have Scoot Henderson ready to fill that role. Is Holiday meant to be a mentor for Scoot?

At last check, Blazers Head Coach Chauncey Billups was encouraging Henderson to play every bit of 5-on-5 basketball he could this summer simply to get reps under his belt. Is a guy who needs to play anytime, anywhere just to survive in this league going to beat out the veteran Holiday? If not, what’s the ultimate upside here, besides bumping out a future hope for a slightly different player? If so, why play $35 million a year to a backup player when Portland doesn’t have enough top-level talent as it is?

Even if we grant that Holiday is more talented than Simons in certain spheres, how wide is the gap? Is it enough to vault the Blazers into contention? Not even the most ardent Holiday fan—nor the most fervent Simons detractor—would argue that. The end result of this deal might be a few more short-term wins for Portland if Holiday has a ripple effect with Henderson, Shaedon Sharpe, and the other young players on the roster. Given Holiday’s age, it won’t be more than that.

It’s not enough. And there’s not one other tangible thing you can point to in this trade that makes a difference or makes its attendant sacrifices make sense, let alone balance.

A few “maybes” might tip the balance the other way.

Maybe Simons had such low value on the trade market that this was the best possible deal for him. But if that’s so, wouldn’t it make more sense to let him leave in free agency next summer instead of spending assets and money to rid yourselves of him a year early?

Maybe the Blazers feel Holiday has future trade value. At 35, that will only diminish. His compensation level won’t. Either way, it’s hard to imagine Holiday having greater worth than in 2023 when the Blazers traded Damian Lillard for him or right now when they’ve done it again with Simons.

Maybe the Blazers are looking at the future draft picks gained from that Lillard trade, plus one outstanding owed to the Chicago Bulls for a long-ago acquisition of Larry Nance, Jr. That owed pick is lottery-protected. If the Blazers don’t convey it soon, they could run into a situation in 2028 where they have to give it to Chicago. If that happens, they’d lose the right to swap with the Milwaukee Bucks, who by then might be a lottery team. But this is an awfully big added expense just to avoid that potential eventuality.

(Side Note: For those arguing that the Neil Olshey era ends with Simons’ departure...no it doesn’t. That first-round pick owed for Nance, Jr. is the gift that keeps on giving and the last mark on Olshey’s ledger.)

Or maybe the Blazers really do value the championship experience Holiday brings. But what good is championship experience if you’re not within 60,000 miles of an actual title? Are the Blazers now going to vault the San Antonio Spurs, Oklahoma City Thunder, and Houston Rockets because Jrue Holiday came on board? If not, what are they spending and/or aiming for?

There’s always a possibility of other unforeseen moves down the road. Trading Henderson? Packaging Holiday with somebody else for a major player? Who knows?

We’ll deal with those moves if and when they happen. Right now I’m pretty confident in saying that if this is the plan, it makes little sense. Less flexibility, more expense, more age, fewer draft assets, and a wash in talent (at best) isn’t balanced by gaining experience, a championship pedigree, and better defense on a team that’s unpolished and unfinished anyway. Pay a fortune to recruit a fantastic driver for the Indy 500. If you put him in a Volkswagen Bus, those skills are likely to go to waste.

The Blazers either needed a big swing this summer or more long-term growth investments. This isn’t either of those things.

I fully expect to be able to applaud several of the things Jrue Holiday does for this franchise. I also expect them to amount to not much more than Simons did or future cap flexibility would in the end. Whatever the ultimate goal is, this isn’t it.

If Portland flips Holiday for assets they couldn’t have gotten with Simons, I’ll applaud and acknowledge their vision. If Holiday somehow transforms this franchise into a real contender—either by himself or after subsequent moves—I’ll be happy to say I was dead wrong. But right now it’s hard to see how the Blazers are investing in anything but sustained mediocrity by chaining themselves to a mismatched, Frankenstein roster.

And that’s if Holiday stays productive and healthy. If he ages out or gets injured in any way...woof.

Given the situation, it’s hard not to feel like Principal Seymour Skinner arguing with Edna Krabappel, trying to avert a teachers’ strike by saying that the faults in the school system don’t matter because the students don’t have a meaningful future anyway. This elicits a gasp from everyone who hears it, which includes an entire cafeteria full of those same children. His injunction to the students at that moment seems the most appropriate thing to say to the Blazers in this one:

Prove me wrong, kids. Prove me wrong.

Please.