The Boston Celtics get down to business

The Draft Day Trade Grade Megapalooza, featuring the Pelicans and Wizards

I almost wrote a Jrue Holiday trade grade piece right after the Portland/Boston trade news broke, but life intervened, and I ran out of time. Good thing! A lot more happened in the last 24 hours; I’ll run through the big stuff.

Like Brad Stevens, let’s get down to business.

Boston Celtics / Portland Trail Blazers

Boston gets: Anfernee Simons, two second-rounders
Portland gets: Jrue Holiday

Boston shipping Jrue Holiday out was fait accompli, but the landing spot and return were a surprise.

Let’s start with a quick acknowledgment of the just-turned-35 Holiday, who has been one of my favorite players for years. He’s one of the league’s best humans and most beloved teammates, and those aren’t empty platitudes: Holiday is a three-time winner of the Teammate of the Year award, two-time winner of the NBA’s Sportsmanship award, and one-time winner of the Social Justice Champion award; he won the latter two just this season!

(It must be nice to have so many shiny plaques affirming you are, in fact, a good person.)

Holiday has been an elite player on two different championship teams, pairing Rottweiler defense with timely shooting and proficient ballhandling. His resume, both on and off the court, overflows.

However, time comes for us all. I put Holiday on my All-Defensive First Team in 2024, but he took a big step back last year. He remains a versatile and powerful defender, but a surprising number of my game notes speak to how relatively easily ballhandlers were blowing by him this season compared to years past. The defense is good still, but I’m not sure it’s great anymore.

And the D way outpaced Holiday’s offense, which saw him post his worst efficiency numbers in a decade while taking a reduced role.

Holiday is still a good player in a vacuum, but we know players don’t live in Dysons. His contract is a killer — three more years at over $100 million. Most of the league would not view him as an asset, although I thought some would-be contenders might sniff around him. I’d love to have seen him in an Alex Caruso super-sub role, where he can conserve his energy and wreak havoc on defense for a team that needed a role player with a championship pedigree.

Instead, Holiday landed in… Portland? Huh.

Once again, Portland will be incredibly fun to watch. Their best defensive lineups could rival OKC’s, Orlando’s, and Houston’s (Holiday, my beloved Toumani Camara, Donovan Clingan, Matisse Thybulle, Deni Avdija, Robert Williams III… they have some dawgs). Coach Chauncey Billups’ greatest strength has been his madcap, press-heavy defensive scheme; Holiday should fit into that like a hand model’s moneymaker into a Versace glove.

Offensively, if Holiday can rediscover his three-point mojo, he might be of some benefit as a spacer and secondary playmaker.

But again, Holiday is 35 and still commands big minutes. Portland is very much in the midst of a youth movement. They have no idea if anyone on their roster is even an All-Star, much less a tentpole offensive player. Scoot Henderson showed signs of life in his second year (I’ll have more on him later this summer), but it’s far from certain he’ll ever be even an average-quality starter. Shaedon Sharpe’s shotmaking and athleticism bedazzle, but perhaps shine so bright they’ve blinded the Blazers to his many flaws. I love Deni Avdija, but he’s not a future superstar. Jerami Grant is getting worse, not better.

Simons was likely Portland’s best offensive player. Holiday can’t replace his shooting or off-the-dribble dynamism, and the Blazers may struggle tremendously to score the ball.

I keep seeing this framed as a win-now move for a team that has yet to break .500 in a season (even if they did finish 23-18). Perhaps it’s a little subtler than that. Perhaps lead executive Joe Cronin wanted to bring Holiday in to be a super-mentor to Henderson, Sharpe, and whoever they draft with the #11 pick tonight. He seems well-suited to the role, and both Henderson and especially Sharpe could use a lot of guidance defensively, in particular.

But there aren’t many teachers in the US of A making $32 million next year.

Maybe Holiday imparts all his wisdom, Henderson lives up to his #2 pick billing, Sharpe becomes a supercharged Zach LaVine, the young supporting cast gels and improves, and the team becomes a perennial top-four seed in the West. Then, we can look back at this as a major turning point for the Blazers.

But that vision smacks of fantasy, not plausibility. Right now, the Blazers are suddenly very expensive and still very much lacking the most important part of teambuilding. Worst of all, reports have come out that Holiday may be “pissed” about going to Portland. I don’t know how true that is, and I doubt he’s anything less than the complete professional he’s always been, but it’s still not what you want to hear if you’re the Blazers.

Portland Grade: D+

My feelings for Boston are significantly more complex.

Next year will be a reload period for Boston, even if they make the playoffs. Without Tatum, cutting payroll became offseason priority numero uno. I’ll talk about the finances more in the Porzingis section below, but consider that boring mission accomplished.

On the fun side, Simons is a fascinating player to consider in the context of Boston coach Joe Mazzulla’s system.

Although his three-point accuracy dipped last year to 36%, we have a long track record of Simons being a deadeye shooter off the catch or the bounce. Simons’ ability to create his own threes will be a particularly interesting fit. After years of groaning after every awkward Tatum and Brown stepback (yes, yes, they’ve made plenty, but you know what I mean), Boston faithful will delight in Simons’ smoothness:

He is a proven 20-point scorer who should juice up Mazzulla’s drive-and-kick system as both a ballhandler and a spacer (although he leaves me wanting a bit as a finisher at the rim in both quantity and quality, which may be a product of Portland’s poor spacing over the years — we’ll find out soon). He’s not a fantastic passer, but the reads in Boston’s system will be much easier than in Portland’s congestion.

All that said, there’s a real world where Simons simply can’t get on the court enough to matter, because when I tell you he might be the league’s worst defender — actually, let me just show you. Here is Simons’ Defensive-EPM percentile by season:

That’s three years out of the last six where he grades out as a first-percentile defender! Nuclear waste handling laws prevent me from sharing his defensive film with you.

In short, Simons is slow to react, abhors touching or being touched by his opponent, rarely creates turnovers, and generally goes through the motions. It’s a subtle misery; it will look like he’s trying, but then you’ll realize that the ballhandler is between him and the hoop for the thousandth time in the game.

It’s one thing to be a bottom-decile defender if you’re Trae Young; it’s quite another when you’re 6’3” with good lateral quickness and kangaroo hops (Simons even won a dunk contest a few years ago!). The Celtics’ defensive success hinges upon giving opponents nobody to attack; Simons will be under siege at all times. If he can’t hold his ground, I don’t think Mazzulla will hesitate to bench him, and bench him hard.

The good news: Simons will be motivated to put in the work, as he’s in a contract year. Boston seemingly wants to test Simons out. The offensive gifts are proven, not just hypothetical, and he could be an excellent long-term partner next to Tatum and Brown if he can iron out his decision-making and defensive woes. Simons will want big money, but he’ll have to prove that he can contribute to winning at a high level for the C’s (or anyone else) to consider shelling out.

Let’s be clear: The big victory here is getting off of Holiday’s expensive contract without paying for the privilege. There’s also enough on-court upside for me to be at least mildly intrigued, even if I’m pessimistic about the history of lazy, soft defenders suddenly becoming workhorses. Boston probably could have gotten back a lower-risk, lower-reward return for Holiday from a contender, but the Simons swing isn’t a bad one.

Boston grade: B

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Boston Celtics / Atlanta Hawks / Brooklyn Nets

Boston gets: so much money freed up, Georges Niang, a second-rounder

Atlanta gets: Kristaps Porzingis, a second-rounder

Brooklyn gets: Terance Mann, the 22nd pick tonight

It’s rare to see win-win-win trades, but that’s what we’ve got here!