The NBA offseason started two days ago, and four star guards are already in new garments (as are Kevin Durant, Desmond Bane, and Kristaps Porzingis). This has been a chaotic summer and it’s only just begun!
Here are my immediate thoughts on the Jrue Holiday and Jordan Poole trades, which I think were the most unexpected of the five that have gone down so far:
Trade #1
Boston Celtics receive: Anfernee Simons & two future second-round picks
Portland Trail Blazers receive: Jrue Holiday
The writing was on the wall for Boston to make cost-cutting moves this summer, but this specific trade came all the way from left field. If he got traded, it felt like Jrue Holiday would end up with a playoff team, but instead he’s heading to Portland for the second time in two years. That’s right— in case you forgot, Holiday was part of the Damian Lillard trade in 2023 but was flipped to Beantown not long after. This time, though, it seems like he’ll be staying in Rip City (although there have been reports saying he’s pretty unhappy with being sent there).
The Blazers walk away from this deal as big-time winners in the short term. Holiday is pretty much the picture-perfect vet for this team. Unlike Simons, he isn’t a high-volume scorer, so more on-ball reps will be available for Scoot Henderson, Shaedon Sharpe, and others in the backcourt. This may be a sign that they’re targeting Jeremiah Fears, Kasparas Jakucionis, or another guard in the lottery. Defensively, Portland has built a really solid foundation with Toumani Camara, Donovan Clingan, Deni Avdija, and Matisse Thybulle. With a six-time All-Defensive honoree now in the fold, this might be a top-ten defense next season. All in all, the Blazers are going to be a serious sleeper moving forward. They have an awesome young core and some quality vets too. Don’t sleep on them.
Boston, on the other hand, is in for a not-so-encouraging 2025-26 campaign. Jayson Tatum’s injury seriously mucked up their plans. The Kristaps Porzingis trade confirmed they’re going all in on a retool. In an ideal world, they probably would have loved to keep Holiday, but at least Anfernee Simons isn’t a bad consolation. The Florida native was once said to be Dame’s heir apparent, and while he hasn’t fulfilled that prophecy, he’s still one of the more underrated combo guards in basketball. He confidently drills threes of all kinds on a high volume, so he’ll be a smooth fit in Joe Mazzulla’s modern attack. Simons isn’t a standout playmaker, but he’s an unselfish decision maker with some lead guard chops. Overall, he’ll compliment Derrick White nicely in the backcourt and will help make up for Tatum’s absence in the scoring department.
The only weird part of this deal for Portland is that they gave up two picks to take on an undesirable contract. Holiday’s on-court and locker room contributions should make it worth it, but still, curious business. For Boston, the main question mark is Simons’ contract, which expires at the end of next year. Will he become part of their core, or is this a rental?
Trade #2
New Orleans Pelicans receive: Jordan Poole, Saddiq Bey, 40th overall pick in Wednesday’s draft
Washington Wizards receive: CJ McCollum, Kelly Olynyk, future second round pick
This deal looks like a random, confusing, nothingburger until you see the financial aspect of it. CJ McCollum, Kelly Olynyk, Khris Middleton, Marcus Smart, and more are all on expiring contracts for the 2025-26 season (whereas Poole has two full years left), meaning next summer the Wizards are projected to have around $100 million coming off of their books. That sort of financial flexibility is a positive no matter what way you spin it. They’ll be able to facilitate other trades in exchange for draft picks, extend any and all of their young guys, and maybe even lure in a notable free agent or two. Money talks, and the Wizards heard it whispering in their ear when they called this one in. In the upcoming season, McCollum and Olynyk can be leaders in the young Washington locker room while also being dangled as trade chips.
While New Orleans isn’t getting the same sort of cap relief, they are getting younger and at least marginally better on the court here. Poole is a McCollum disciple in some ways with his crafty microwave scoring, and the two produced very similarly this past season. Saddiq Bey didn’t play at all in 2024-25 due to an ACL tear, but he’s a career 14.1 point-per-game scorer who can space the floor next to Zion Williamson. The Pelicans still don’t have a clear direction, but turning a 33-year-old and a 34-year-old into two 26-year-olds that are also good players right now is smart no matter which organizational path they choose moving forward.
Overall, the only “loser” here, at least on first glance, is Boston. Simons is a good get, but being forced to break up a championship core this soon is quite unfortunate. Otherwise, Portland, New Orleans, and Washington all did pretty well for themselves.
What do you think about these two trades, and the others that happened recently? Let me know in the comments or on X— my handle is @finleykuehl. Thanks for reading and see you next time!
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