My Five Least Favorite NBA Transactions of the 2025 Offseason Thus Far

Because hating is more fun than staning

The NBA Summer doldrums are almost here. Outside of a few restricted free agents signing deals, meaningful NBA transactions will lay in an airconditioned hibernation until training camp gets underway. Until then, let us relfect on the 2025 offseason that was. Earlier, I listed my five favorite transactions, but in a stunning twist, I’m going to lament my five least favorite transactions.

These are a Few of my Five Least Favorite Things

Bucks Waive and Stretch Damian Lillard

The Milwaukee Bucks’ surprise free agency signing of Myles Turner should have been cause for celebration, but the avenues traversed to secure Turner’s services rendered it a disastrous decision, and the architect of all this misery was the Bucks’ decision to waive and stretch Damian Lillard.

When Lillard went down with a torn Achilles in the Bucks’ first-round playoff series against the Indiana Pacers, it presented the franchise with an opportunity. Yes, this season and next would be lost, but the Bucks now had an out from their taxed-out pretender-contender. Without Lillard, the Bucks could have gone to Giannis Antetokounmpo and said it’s time to move on. It was the perfect and obvious time to end the most fruitful relationship in franchise history (with apologies to Kareem Abdul-Jabbar’s six-season run), recoup a Greek God’s level ransom, and suffer through a few lean years before, hopefully, making it out the other side. Spoiler, that’s the opposite of what the Bucks did.

Instead of moving Giannis to greener pastures, the Bucks went hard to appease him by signing Myles Turner to a four-year, $108.8 million contract with a full 15% trade kicker. To free up enough cap space to actually pay Turner, the Bucks waived and stretched the remaining $113 million left on Lillard’s deal. Now, instead of having Lillard off the books after two seasons, the Bucks will be paying Lillard $113 million over the next five, eating $22.5 million of cap through the 2029-30 season.

This is simply the dumbest and worst move of the offseason. If the Bucks' stated goal is to win another championship with Giannis, this decision will kneecap them throughout the rest of his prime. It’s $22.5 million in dead salary that cannot be moved. At least Lillard, on a massive expiring contract, could have conceivably been used to acquire players. This decision is only made worse by the Bucks using the short-term savings to acquire a player who may not make them that much better anyway.

Turner has a unique skill set as a stretch-five with solid rim protection. For most teams, his addition would add another offensive layer, but for the Bucks, it’s simply more of the same. The now departed Brook Lopez, over the past three seasons, averaged 13.8 points, 5.6 rebounds, 2.2 blocks, and 4.8 3-point attempts per game on 37.1% 3-point shooting. Turner, over the same time frame, averaged 16.8 points, 7.0 rebounds, 2.0 blocks, and 4.6 3-point attempts on 37.7% 3-point shooting. The Bucks didn’t add Turner as much as they replaced Lopez, and considering Turner will be playing next to Giannis Antetokounmpo, there’s a good chance that his points and rebounds advantage disappears.

The Bucks are not better this season than they were last season. In fact, they’re going to be worse because they won’t have Damian Lillard producing at an All-Star level. This was the time to move Giannis, and while waiving Lillard won’t inhibit that, they decided to continue deeper into the abyss. The Bucks, to borrow a phrase from DJ Khalid, “played themselves.” They were so focused on appeasing Giannis that they nuked any chance of ever competing with him. Chances are Giannis will ask out in the next 12 months because this team is nowhere near good enough. And even if he doesn’t ask out, well, the Bucks won’t be very good because they have $22.5 million in dead money haunting them for the rest of the decade.

Jaren Jackson Jr. 5-year $239.9 million Renegotiation-and-Extend

Jaren Jackson Jr. is an exceptional player who deserves a massive contract, but the ripple effects of the Grizzlies’ decision to renegotiate and extend him this summer left a lot to be desired. Let’s start with the basics. Due to the contract Jackson was on, the Grizzlies couldn’t simply extend him for a figure he would ever accept.

The NBA, unsurprisingly, has an incredibly contrived rule that has largely backfired when it comes to extensions. The maximum raise a player can receive from the final year of their contract to the first year of an extension is 140% of the final year of their current deal. So, if a player is making $20 million in the final year of a deal, the maximum first-year salary they can receive through an extension is $28 million. This is only compounded by the fact that player raises can be for a maximum of 8% of their first-year salary.

This was a problem for Jackson, as he was scheduled to make $23.4 million in 2025-26, which meant the maximum first-year salary he could be offered on an extension was $32.76 million with raises of $2.6 million each season. In a world where a 25% maximum contract would net you a starting salary of $41.25 million with raises of $3.3 million in 2026-27, there was just no way he would agree to an extension barring catastrophic injury.

To remedy the situation and lock Jackson up for the foreseeable future, the Grizzlies needed to renegotiate his 2025-26 salary to a higher figure and then extend from that new number, which is exactly what they did. The Grizzlies bumped Jackson’s 2025-26 salary to $33 million through a renegotiation, and then extended off that figure, giving him a 140% raise in 2026-27 for a salary of $46.2 million with $3.696 million raises (8%) each season. And this is where I have a few objections.

The Grizzlies functionally gave Jackson a $10 million raise in 2025-26, to get $5.2 million in savings over the next five years. Yes, the Grizzlies are only saving $5.2 million over five years compared to letting Jackson play out this season at $23.4 million and then signing him for four years at a 30% maximum contract.

So what exactly makes this deal so bad? Well, first, Jaren Jackson Jr. had to have surgery for turf toe while this was being negotiated. Surely, the Grizzlies could have gotten a few more concessions. But that’s secondary to the dominoes that had to fall for the Grizzlies to boost Jackson’s salary by $9.6 million this season. The first domino to fall was the Grizzlies trading Desmond Bane, which they probably would have done regardless, but it necessitated it a year earlier than needed.

However, that move only saved them $2 million before they agreed to a buyout of Cole Anthony, which will save them an unspecified amount, but likely around the $10 million of his $13 million salary after they stretch him. Downgrading from Bane to Kentavious Caldwell-Pope to open up maybe $10 million in cap space is penny-wise but pound-foolish. Then the Grizzlies traded Jay Huff to the Pacers for draft compensation. Huff isn’t a star, but as a center who can hit threes and is on an excellent contract, he’s not exactly someone you want to move in a cost-cutting move.

The reason I hate this decision by the Grizzlies is that they’ve gotten worse when they should be trying to get better, and they basically got nothing in return from Jackson for bumping his pay a year early and locking him into a great deal. Sure, he didn’t get a player option, and they locked in some cost certainty, but that cuts both ways. If the cap rises by more than the projected 7% heading into 2026-27, then the savings will be better, but if the cap rises less, then those projected savings will be eaten into quickly.

Finally, I’m just not sure Jaren Jackson Jr is honestly worth this kind of a financial outlay. As his offensive game has grown the past two seasons, his defense has declined. If he’s not one of the ten best defensive players in the league, will his offense make him a max player? He’s also one of the worst rebounders in NBA history when you factor in his size, which requires him to play significant minutes next to a center.

The Grizzlies bent over backwards and moved an excellent player a year early just to give Jaren Jackson Jr. a near-maximum contract. If the Grizzlies were a team with any appetite to run massive payrolls, I’d feel differently about it, but they always err on the side of cheap. The Grizzlies didn’t need to do this now, and I believe in time, they’ll regret this decision.

Pelicans Draft Day Trade

The New Orleans Pelicans' draft day trade was one of the most head-scratching decisions I can remember. They sent the 23rd overall pick and a 2026 unprotected first-round pick, which will be the most favorable of the Pelicans or the Milwaukee Bucks, for the 13th pick in the 2025 draft. There is a real difference between the expected future contributions of the 13th and 23rd pick, but surrendering an unprotected pick that is linked to a team, the Pelicans, who just had the fourth-worst record in the league, and a team, the Bucks, who are a Giannis Antetokounmpo injury or trade demand away from being one of the worst teams in the league is insane.

The total lack of understanding of the value of that 2026 pick is beyond me. If the Pelicans had shopped it, they could have done far better than moving up from 23rd to 13th. I’d wager the Hawks would have likely considered taking that pick for the 13th pick straight up. While the Pelicans’ utter disregard for the golden ticket they possess is a farce in its own right, the player they selected makes even less sense.

The Pelicans used the 13th pick to select Derik Queen. A highly skilled 6’10 center, Queen is a real prospect, and this critique is not about his future, but he makes next to no sense on the Pelicans. Queen has real offensive upside, but he cannot space the floor and is a poor defender. He’s best with the ball in his hands, and by now, you should have realized that Queen makes next to no sense playing alongside Zion Williamson.

If the Pelicans don’t care about how Queen fits next to Zion because they’re more than happy to get out of the Zion business, that’s fine, but if that’s the case, then why the hell would you trade that 2026 pick? You wouldn’t (hopefully). So, by deductive reasoning, the Pelicans presumably think Queen and Zion will work. I have serious doubts about this because of all the things I stated earlier, and also because Queen might not actually be any good.

While Derik Queen is a real prospect, he’s also an extremely risky prospect. Offensive-leaning bigs who can’t space the floor or defend are the riskiest players to draft. For every Alperen Sengun, there are five Enes Kanters, Jahlil Okafors, and Marvin Bagleys, and Sengun has developed into a passable defender. If these guys don’t hit as real offensive focal points, they’re basically useless players.

The only way this trade looks moderately acceptable is if the Pelicans and Bucks both make the playoffs, and Derik Queen develops into a starting-caliber center. However, if you need three unlikely things to all happen for a trade not to look astronomically stupid, then the trade was unequivocally astronomically stupid. I hope Queen has a great career and we have a revival of offensive-leaning centers, but chances are he’ll be a fine player, one of the Pelicans or Bucks will miss the playoffs, and the Pelicans will have traded the 23rd pick in 2025 and the 13th pick in 2026 for the 13th pick in 2025.

Suns Sign Devin Booker to a two-year, $145 Million Extension

The Phoenix Suns have spent all summer trying to undo the wrongs of their hastily assembled “super team.” First, they traded Kevin Durant to the Houston Rockets for Jalen Green, Dillon Brooks, and the tenth overall pick, which was originally their pick before they sent it to the Nets to acquire Durant in the first place. Then they waived and stretched Bradley Beal to add $19.2 million in dead money to their books over the next five seasons to save untold millions in luxury tax payments. But in between jettisoning the two failed super-friends, the Suns extended Senior Sol himself, Devin Booker, for two years and $145 million.

Booker, who will turn 29 on October 30th, was already under contract for the next three seasons at $171.2 million, which brings his pact with the Suns to five years, $316.2 million, and will take him through his age-33 season. As a note, Spotrac has the extension at two years and $133.2 million.

These are the types of deals I absolutely hate: massive extensions for great but not transcendent players who are still under contract for three more seasons. The list of NBA teams that have eventually regretted these massive extensions is long, and it’s only likely to grow when Booker is earning over $70 million during his decline phase.

The truth is that Booker almost certainly isn’t good enough to justify a 35% maximum contract. Box plus/minus (BPM) isn’t a perfect stat, but it’s a publicly available metric that does a good job of discerning player value. Only once has Booker finished in the top-20, when he finished 20th in 2022-23, and he only has two top-20 finishes in offensive BPM, with a high of 4.5.

Booker is a great player, but committing $145 million for his age-32 and 33 seasons to a player who may not be a top-20 player in their prime is a recipe for disaster. Throw in Bradley Beal’s $19.2 million in dead money that will be haunting the Suns for the remainder of their current contractual obligations to Booker, and there’s a strong likelihood that the Suns' next contender will be in the 2030s when Booker is decidedly past his prime.

Now, if the Suns had seen the light, they would have realized that their best path forward would be an actual rebuild spurred by moving Booker. At some point over the next five seasons, it’s incredibly likely that Booker will get fed up with being on, at best, a low-level playoff team and ask for a trade. The problem is, I doubt any team will be willing to move heaven and Earth to get Booker when he’s making $70 million.

The parallels between the deal the Suns gave Booker and the one Bradley Beal was just bought out of are jarring. The Wizards signed Beal to a five-year, $250 million contract in the summer of 2022. Beal was entering his age-29 season, had made third-team All-NBA the prior season, and had finished in the top-20 in offensive BPM twice, with a high of 5.3. I mean, just look at their careers through their age-28 seasons.

I’m not necessarily trying to suggest that Beal was just as good as Booker, but if Beal’s deal went so horribly wrong, then the likeliest outcome is that Booker’s will go poorly as well.

While I understand why Booker put pen to paper (how could you not?), I think he and the Suns are stuck in a situation destined to suck. Given where the Suns are currently, they have little hope of contending with Booker, and with where Booker is contractually, the Suns and Booker will have little hope of finding a trade. There is value in keeping a franchise icon around, but I have a feeling this situation is going to end messily, when it could have been an amicable split that benefited both sides.

Portland Trailblazers Trade for Jrue Holiday

The Blazers’ trade for Jrue Holiday is an All-time basketball headscratcher. Usually, there is a theme to a front office’s offseason. A tanking team will jettison veterans, a contender will flip picks for players, and the Bulls will build a 38-win team. However, the Blazers’ offseason, headlined by their acquisition of Jrue Holiday, has had no rhyme or reason.

This Summer, the Blazers have turned Anfernee Simons into Holiday, traded the 11th pick for the 16th pick and a future pick, not extended Shaedon Sharpe, bought out Deandre Ayton’s $35.5 million salary, and then signed Damian Lillard, who will miss all of 2025-26 recovering from an Achilles tear, to a three-year $42 million contract. Maybe I’m missing something, but the Blazers seem to be trying to build for the future, while also making a win-now trade, and getting substantially older.

The asset outlay for Holiday wasn’t massive, but there’s a case to be made that Simons will be better than Holiday in his age-35 season, and the financial implications are substantial. He’s owed $67.2 million over the next two seasons before a $37.2 million player option for his age-37 season. When you factor in that Holiday’s best season with the Blazers is likely going to be this season, it makes their decision to functionally create $49.5 million in dead money this season by waiving Ayton and signing Lillard even stranger.

Now, I understand Blazers fans will say a bunch of illogical shit in response. They’ll say Simons, who is 26 and only making $27.6 million this season, is on an expiring contract and not as good as Holiday. The contract part is true, and the talent evaluation is potentially, but I’d rather have Simons on an expiring contract than Holiday for three years and $104.4 million as he approaches 40. They’ll also probably say, “He’s a good veteran presence.” Fantastic. I love a good veteran presence, it’s what makes the American Legion so completely not depressing, but that’s an insane amount of money to spend on a presence, and it’s even more insane when you already have Jerami Grant on the roster, and then you signed Damian Lillard, who will only be a veteran presence next season.

Unfortunately, I think the Trailblazers believe they’re ready to make a leap, which is a massive miscalculation. The Blazers went 36-46 last season, finishing 12th in the Western Conference. They were almost a play-in team, but they beat their expected record by three games, and I don’t think Holiday is adding ten wins to your record at this stage in his career. However, I think the Blazers are overreacting to a decent post-All-Star Break run. Before the All-Star Break, the Blazers played to a 23-32 record, but then stormed to an incredible 13-14 record down the stretch. Here’s the problem with that brief run of Bulls-level mediocrity– it was a mirage.

For those 13 wins, they beat the Hornets, Jazz, Nets, Sixers, Wizards (twice), Raptors (twice), Spurs (post-Wemby and Fox), Hawks, Lakers (last day of season, nothing to play for), and the Grizzlies and Nuggets right before they both fired their coaches. The Blazers did post a +2.4 net rating over that stretch, but this team isn’t close to the playoffs with Holiday, and they’ve spent this entire offseason completely screwing up their future cap sheet.

The Blazers, at minimum, will be paying Grant, Holiday, and Lillard $83 million in 2026-27, and will then be staring at least $87.6 million in player options for their age 37 and 33 seasons. Hopefully, Shaedon Sharpe and Scoot Henderson will have shown enough that they’re on decently sized extensions, which would bring the Blazers to at least $135 million in salary commitments for five players.

Jrue Holiday is a Hall of Famer and still a solid player. Unfortunately, time has started to catch up to him, and he’s owed a ton of money. The Blazers should be tanking. They don’t yet have a franchise cornerstone and seem intent on building a watchable but ultimately bad team. Even if Sharpe and Henderson pop this season and they’re a viable play-in contender, they’ll still have three bad deals for geriatric contributors preventing them from adding impact players that fit their timeline. The Blazers feel like a team that’s being pulled in two directions, where one understands reality, and the other is listening to Portland sports radio for direction.

For any inquiries about work, discussion, and the like, you can email me at nevin.l.brown@gmail.com.