Brad Stevens Makes His First Big Trade Of The Summer By Sending Jrue Holiday To The Blazers For Anfernee Simons

Maddie Meyer. Getty Images.

With the NBA Draft quickly approaching, anyone who has been paying attention to the words of Brad Stevens knew that the first trade domino was going to drop at any moment.

When you then look at Brad's history as GM of the Boston Celtics, he's shown on multiple occasions that he's going to pull the trigger on something ahead of the draft

So what do we get? Wouldn't you know it, our first Shams bomb of the offseason

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FROM THE CLOUDS

See this is why Brad Stevens is the greatest. Let me ask you, did you hear a single Celtics/Anfernee Simons rumor? Single report? A single source? Nope, you sure as shit didn't. You heard the same non-news updates we all did and in reality Brad was working behind the scenes executing our first big trade of the Celtics offseason. We knew Jrue was most like going to be one of the large salaries that had to be moved this summer. I think most had come to peace with that. It fucking sucks and I wish it wasn't the reality of this new CBA world, but it is. Worth it? Hell yeah. Jrue Holiday is a Celtics legend for the rest of his life as far as I'm concerned. He delivered the exact thing he was brought in to do and what we all hoped he would do. How he elevated his play in the playoffs, it was an honor to watch it.

But the money had to go. It's Brad's job to make a tough decision and find the best way to make that happen, and here's how he did

This is why relationship building is important. It's clear Brad and Joe Cronin have a great relationship, seeing as how he's the GM that gave the Celtics Jrue in the first place. Now here he is a few years later taking that same player back at additional years and money and in return flipping their best player? At the very least, their best scorer and #1 option?

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With Jayson Tatum sidelined for the season, the Celtics offense is a bit of a disaster at the moment. Especially witht he unknown about some of the other guys in the roster. The point is, for 2025-26 they're going to have to find other ways to score that aren't "Please bail us out Jayson", and Anfernee Simons can score. 

The next era of Celtics basketball is going to require Brad identifying talent and surrounding Tatum with players good enough to contend by the time he's back. Simons age fits their timelien and the talent is certainly there. There's big time defensive issues, but now he gets to be molded by Joe Mazzulla. The same way Brad hit on Derrick White developing offensively, what if this is his bet that he can mold Simons defensively? Given his offensive skillset he should thrive in Mazzulla Ball, especially in a year where the shots are going to be there for the taking. 

There's also the contract aspect of it. As an expiring, at the very worst Brad can flip him at the deadline for additional rebuilding assets, but if it works out? This is a great piece in theory for the next iteration of this team. I trust Brad's ability to evaluate existing NBA talent and finding players that fit his system. 

In the meantime, you take a chunk out of the 2nd apron that you need to trim and you position yourself for the next move. According to Shams, that could be anybody. I'll be honest, I'm a little freaked out at the moment. I can't stop refreshing my timeline. Brad has pulled the trigger, we're officially off and running.

No pressure or anything, only the entire future of the Boston Celtics is at stake. Good luck!