Stevens' Sucker Punch: Analyzing the late-night Jrue Holiday trade
A top-down look at how the deal affects the Celtics
Brad Stevens struck us with a sucker punch. I woke up at 5 am to my phone going nuts. At this time of year, that only means one thing: The Celtics made a trade.
With a Thanos-like snap of his fingers, Stevens sent Jrue Holiday to the Portland Trail Blazers, with Anfernee Simons and two future second-round picks heading back to Boston.
Let’s start peeling some layers off and see if we can find any Easter Eggs.
The Money Aspect
I’m putting my weakest forward here.
We all know that Boston’s cap situation is an issue. Before the Holiday deal, the Celtics reportedly faced a $500 million payroll for next season, once luxury taxes were included.
Moving Holiday is the first step to ducking under the second luxury tax apron, avoiding the repeater tax, and breaking free of the restrictions that come with being a second apron team.
Bobby Marks, Keith Smith and Yossi Gozlan all reported that by moving Holiday, the Celtics are now $18 million over the second tax apron. That includes the incoming salary of Simons, which will be $27.6 million this season, per Spotrac.
However,
reported via X that trading Holiday has shaved off roughly $41 million in potential luxury tax payments.Joe Mazzulla loves The Town, but even Charlestown didn't see this much money vanish into thin air - huge savings from Brad, who continues to operate with the stealth of a real-life ninja.
Gozlan then noted that when factoring in the $4.7 million difference in Simons and Holiday’s deals, Boston has walked away from the trade with a total saving of $46 million, which includes the impending salary of whoever the Celtics select with the 32nd pick on Thursday.
I would assume the salary of whoever Boston selects at 28th will impact those savings, although I am unsure of how much, or if my assumption is even correct.
The CBA is far from my strong suit.
I defer to Smith, Gozlan and Marks on all things cap-related. Those guys are geniuses.
The Jrue Holiday Side Of Things
When the Milwaukee Bucks traded for Holiday, they went on to win a championship that same season. When the Celtics traded for Holiday, history repeated itself.
Now, I’m not saying Portland is about to emerge as a championship contender. What I am saying is that Holiday provides championship-level impact. The Celtics will struggle to replace his versatility on both sides of the floor.
If you play chess, you will know how important the queen is. It’s the only piece that can move any number of squares horizontally, vertically or diagonally. Holiday was the Celtics’ queen. From his cross-matching onto bigs to his dunker spot playmaking and scoring, he filled roles that aren’t usually assigned to guards. He moved how he wanted and where he wanted, making an impact as he went.
Jaylen Brown will undoubtedly be tasked with taking over as the primary on-ball defender. We saw what Brown is capable of during the 2024 championship run. Without Holiday, the Celtics need that version of Brown.
Even then, Mazzulla’s chessboard will look different. We’ll likely see less cross-matching, and peel switching could become a less frequent occurrence. Fortunately, the Celtics still have Derrick White and Brown to help anchor the perimeter. It’s just that Boston now has a two-headed monster rather than the Cerberus we’ve become accustomed to.
Offensively, the Celtics are losing a connector—someone who can hurt teams as a screen-and-short-roll threat, a corner 3-point threat and a scorer off the catch or the dribble.
Holiday ended last season with 239 total assists, 27 blocks, 66 steals, 108 made 3’s and 146 made 2’s. His impact was everywhere, just as you would expect.
Beyond the X's and O's, Holiday was a steady hand when games got tight. While Tatum and Brown provided the fireworks, Holiday made the right play, took the right shot, and rarely seemed rattled. That kind of championship DNA is exactly why this trade hurts, at least a little. It’s also the precise reason why the Trail Blazers likely view him as the ideal veteran presence to help improve the young roster Billups is marshalling.
That leads us to Simons.
The hope is that what the Celtics lose in defense, Simons helps replace with additional offense.
Look, I’m not going to lie to you. Simons’ defense is bad—like really bad. We’re talking Ben Affleck as Batman level of bad here.
My hope here, is that the Celtics have enough high-level defenders, with enough size and length, that they can hide Simons on the defensive end. However, we all know Mazzulla will test Simons’ fortitude at times and force him to guard his yard in isolation.
If you want to play for Mazzulla, you’ve got to meet him where he’s at on the mental battlefield.
Still, if we look past the defensive issues, there’s a lot Simons can bring to the table. His 3-point offense perfectly fits the current system, with 50% of his offense coming from the perimeter last season. Simons likes to operate between the wings and the top of the perimeter. He can handle the rock, work off-ball, and create for himself or others.
This past season, he shot 37% from deep on 214-of-575 shooting from deep. If the Celtics can retain a high degree of spacing, I wouldn’t be surprised to see that average start trending closer to 40% this season.
10% of Simons’ offense also came between the free-throw line and the 3-point line, meaning he has no problem attacking closeouts off the bounce before pulling up in the mid-range. What’s encouraging is that he shot 52% on those close-out busting shots, giving him a DeRozian counter to his perimeter-based game. Volume-wise, Simons shot 56-of-107 from the long mid-range area last season.
I will be doing a deeper dive/film study on Simons tomorrow. Make sure to subscribe if you want that sent straight to your inbox!
Simons led the Trail Blazers in touches per game last season, with an average of 65.1 per night. That means he was viewed as the team’s primary playmaker, both in terms of his own offense and for others. He also sat second on the team for average time per touch with 4.49 seconds, which would have placed him second on the Celtics roster, above Payton Pritchard, who averaged 4.20 seconds per touch.
420, nice…
So, it will be interesting to see how easily Simons adapts to additional off-ball reps, or whether Mazzulla will keep the ball in his hands and continue to use Derrick White in a primarily off-ball role.
That’s a question for another day. Nevertheless, the Celtics have a lot of mouths to feed on offense, so Simons can’t let the ball stick.
Another question I have is whether Simons will help the Celtics play at a higher tempo next season. With Brown expected to be the primary option on offense, it’s logical to add some zip into the offense. Brown is at his best when charging through the open court, either to explode around the rim, snake to his spots in the mid-range or create enough defensive movement that he can pick a pass to an open shooter.
Simons should be able to match that tempo and pace of play, ensuring Brown has an additional ball-handler to ease the load and an elite scorer to keep defenses honest.
I like the optionality Simons provides for Boston. I also like that he has a year with limited expectations on his shoulders before potentially being part of the pressure cooker that comes with a contending-level roster.
Of course…
We Have To Ask Questions About That Contract..
Here’s the key wrinkle.
Simons is in the final year of his current deal. He’s extension-eligible.
Stevens has two choices.
Keep Simons, see how he adapts and fits with the roster and then look to extend him.
Flip him in another deal
There is a third choice, which would be to keep him for this season and then wave goodbye in free agency — but, as you can probably tell, I’m not buying that as a genuine option. Stevens isn’t going to let an asset like Simons just gallivant into the ether.
Shortly after the trade, Adam Himmelsbach of the Boston Globe reported that the Celtics liked Simons because of his offensive skills.
“A league source said the Celtics acquired Anfernee Simons, who is on an expiring deal, because they like what he can bring to the roster, but added that they will "remain engaged on all fronts."
Given Himmelsbach’s report, I’m leaning toward the notion of the Celtics keeping Simons around and figuring the rest out later. To be honest, I’m excited about what the fit could look like and how the Celtics could blend some of the Indiana Pacers’ concepts into the rotation now that Simons will also be on the floor.
Still, Stevens moves in silence. So, I’m not ignoring the fact that other trades are likely on the horizon, and one of them could potentially feature Simons.
Such is the life of a Celtics fan right now.
Watch this
I was joined by Billy Calabrese and Bruce Veliz of Celtics Digest to discuss the trade. This video was recorded at 5:45 am UK time, so forgive my grogginess. I hadn’t long gotten out of bed.
Where’s your head at?
How are you feeling about this trade? Do you like the fit? Hate it? Apathetic toward it?
Let me know in the comments section!
Simons is such a sieve. I’m looking forward to seeing if Joe and the staff can get him up to a not embarrassing level.
Also, Ben wasn’t that bad (ducks)
I like the trade for the reasons you noted, including that his contract will be much more tradeable at the trade deadline and that the team didn’t need to include and draft assets to move Holiday’s contract. If Simons stays, it will be interesting to see whether Mazulla can coach him up to be an average defender, although his height is a drawback. He can score, and do so reasonably efficiently.