Biggest Regrets from the 2023 NBA Trade Deadline
You know what they say about hindsight: It's great for determining which teams should want a mulligan on the 2023 NBA trade deadline.
Regret is a powerful emotion, and assigning it to basketball organizations is certainly going to rub certain fanbases the wrong way. But this exercise isn't meant to mock or mudsling.
Sure, in some instances, it seems like franchises messed up—big time. Mostly, though, this is a look at which teams should have strived to do more and aimed higher during the Association's transaction tumult.
To that end, these selections weren't taken lightly or chosen haphazardly. Every team is at the behest of the trade market and its available assets. There needed to be a clear path to better alternatives or an obvious mishandling of situations for each squad to appear here.
And finally, this list isn't meant to represent how every team feels. They will all maintain that they're comfortable with their direction or that everything at the trade deadline went exactly according to plan.
These regrets are instead presented from an outsider's perspective. We should have all expected more or better from these teams—because they needed it.
Potential Regrets
1 of 5
Chicago Bulls
The Regret: Doing absolutely, positively nothing at the deadline.
This should theoretically be a "Why didn't the Bulls blow it up?!" diatribe. And, well, it's a little of that. But Chicago has been on a tear since the All-Star break, going 8-4 with a top-eight offense and top-two defense.
DeMar DeRozan and Zach LaVine are playing surface-of-the-sun basketball. The Patrick Williams and Coby White bandwagons are visibly more crowded. Patrick Beverley is the best buyout pickup to date.
So, like, maybe the Bulls should have been more aggressive in seeking upgrades? Except, well, they're still 10th in the East. So maybe they should have blown it up after all? Or perhaps just chilling was perfectly fine? (*shrugs*)
New Orleans Pelicans
The Regret: Failing to meaningfully upgrade their three-point shooting, rim pressure or frontline rotation.
ESPN's Zach Lowe noted on a recent episode of The Lowe Post podcast that New Orleans came close to completing a deal with Utah for Malik Beasley and Jarred Vanderbilt before the Los Angeles Lakers swooped in. That would have been perfect.
Nabbing Josh Richardson and getting off Devonte' Graham without forking over a first-rounder was fine. But the Pelicans needed more offensive juice. They are 24th in points scored per possession since Zion Williamson went down, with a shot profile disastrously light on rim attempts and three-point volume.
New Orleans now seems destined to finish outside play-in territory after flirting with top-of-the-West status heading into the New Year. That's...problematic. But should the Pelicans have been aggressive at all when Zion has no timeline return? I'm honestly not sure.
Sacramento Kings
The Regret: Failing to upgrade the perimeter defense beyond the acquisition of Kessler Edwards.
This "regret" is actually a compliment. The Kings are so good and fun that it would have been nice to see them angle for more than a Kessler Edwards acquisition—someone who can soak up even more minutes on bigger wings while decreasing their dependence on Davion Mitchell. Jacking up their big-man minutes behind Domantas Sabonis would have been neat-o, too.
Declaring full-on regret is a little too nitpicky in the end. The Kings are contending for a top-two seed in the West, and despite their defensive shortcomings, they do a good job crashing the glass, limiting their fouls and forcing rival offenses to work deep into the shot clock. Both Trey Lyles and Chimezie Metu are also helping the non-Sabonis minutes evade complete crap-fests.
Messing with the vibes in Sacramento would have been risky, and the team's first-round obligation to Atlanta in 2024 (lottery protected) complicated bigger-time aspirations. The Kings are probably better off gauging where they stand in the playoffs and tinkering over the offseason. This doesn't mean I'll stop wishing they joined the pursuit for Jarred Vanderbilt, Saddiq Bey, Josh Richardson, Jae Crowder or another wing from Brooklyn.
Memphis Grizzlies
2 of 5
The Regret: Playing it safe again despite contending for a top-two Western Conference record.
The Memphis Grizzlies have long flown in rarefied air. They are a title contender, or something extremely close to it, with the assets necessary to make a gigantic splash while holding onto their three best players (Ja Morant, Jaren Jackson Jr., Desmond Bane).
Refusing to act on this comfy position is one thing if you're a finished, near-infallible product. The Grizzlies are anything but. They have distinct flaws—entrenched weaknesses on offense that are glaring enough to derail their championship hopes.
Yes, Memphis ranks 10th in points scored per possession. And sure, the progression of JJJ and another mega leap from Bane is nothing at which to sneeze. But the collective attack continues to subsist on transition opportunities and second-chance buckets while lacking functional shooting and from-scratch creators.
The Grizzlies are 19th in three-point-attempt rate, 22nd in long-range accuracy, 25th in catch-and-shoot effective field-goal percentage and 22nd in overall half-court efficiency. This is not an offensive makeup that screams, "playoff-ready!"
Landing Luke Kennard ironed out some of the wrinkles but not all of them. And the offensive oomph he provides is not without trade-offs. Kennard is drilling 48.6 percent of his three-pointers in Memphis. The Grizzlies are also surrendering 117.6 points per 100 possessions with him on the floor (26th percentile).
Caveats abound. Many of Kennard's stints come without one or both of Jackson and Dillon Brooks, and that's on top of Steven Adams' absence. Memphis is winning the minutes Kennard plays, and in a somewhat stunning twist, it ranks 10th in half-court offense since the trade deadline despite not having Morant for nine consecutive games (and counting).
Still, hellacious defense and all, the Grizzlies are not a contender who profiles as a prohibitive favorite. Their offense remains vulnerable, and without Adams or Brandon Clarke, their playoff rotation stretches maaaybe six trustworthy players deep.
Changing things up requires a market conducive to doing so. This year's deadline wasn't awash with opportunities. Plenty of teams were pearl-clutching, and just like 28 other squads, Memphis never had a realistic chance to enter the Kevin Durant business. It did, however, have the assets to aim bigger than Kennard and turn said pearl-clutchers into open-minded negotiators. (Kyle Kuzma? Bojan Bogdanović? Jerami Grant?)
Sentiment will shift if the Grizzlies make a run to the Western Conference Finals. It shouldn't. The point here isn't to infer that they suck. They don't. They're awesome. But they have the goodies to be so much better. And yet, dating back to the offseason, they continue to function like a team on a more gradual timeline.
Denver Nuggets
3 of 5
The Regret: Selling low on Bones Hyland without improving the defense or landing a top-seven rotation player.
Evaluating Bones Hyland's exit from the Denver Nuggets is all sorts of complicated.
Flipping him for what amounted to Thomas Bryant is beyond unspectacular in a vacuum. Hyland wrapped 2021-22, his rookie campaign, as a darling prospect—an electric bucket-getter with limitless range, contortionist handles and finishes and the vision, at times, to be more than just a microwave scorer.
Giving up on him at age 22 with two years left on a cost-controlled contract necessitated getting more than a backup 5 fated to average fewer than 12 minutes per game and rack up a handful of DNPs.
Then again, reality is different from a vacuum. Hyland's value plummeted, both on and off the court. He wasn't a part of Denver's rotation by the trade deadline, and he's not part of the L.A. Clippers' regular rotation now.
To what extent the Nuggets are responsible for Hyland's precipitous fall is a matter of perspective. They wouldn't deliberately accept a rock-bottom return if better offers were out there; what else were they supposed to do if he was an active drain on the locker room? At the same time, there's no way this situation deteriorated overnight. If they had any inkling this would go sour, they should have acted sooner or been prepared to play the much longer, more arduous game.
Regardless, the bigger regret exists independent of the Hyland soap opera. Denver's rotation has wanted for a clear-cut seventh man, better backup 5 minutes and defensive reinforcement. Acquiring Bryant could only ever check one of those boxes. In actuality, it has addressed none of them.
The Nuggets, meanwhile, have slipped to 18th in points allowed per possession since the trade deadline and are 22nd since the All-Star break. Bryant barely plays, the defense dips when he does, and Denver's search for a reliable seventh man soldiers onward, spanning everyone from Reggie Jackson to Jeff Green to, most intriguingly, Christian Braun.
Once more: The question of "Well, what else were the Nuggets supposed to do?" hovers over this entire discussion. They did not have the capacity to bag a seventh-best player without bankrupting what few assets are still in their armory. That doesn't make their deadline any more palatable. They ended up punting on someone who, mere months ago, was among their most prized trade chips without adequately remedying their biggest issues.
Miami Heat
4 of 5
The Regret: Relying on the buyout market instead of trades to upgrade the frontcourt rotation.
"Nobody wants to face the Miami Heat in the playoffs!" is common refrain among basketball intelligentsia, particularly inside South Florida. It might be true.
Bam Adebayo's Defensive Player of the Year case is once again flying under the radar, and Jimmy Butler, who's somewhat quietly piecing together another All-NBA campaign himself, remains one of the most terrifying postseason performers in the business.
And yet, what if almost everybody should want to face the Heat in the playoffs?
This is a logical conclusion when digging into their offensive vitals. Miami is 25th in points scored per possession and has been only slightly better since the trade deadline (21st). Watching its half-court attack is equal parts chore and eyesore.
Nobody outside of Butler (and maybe Caleb Martin, by way of cuts) generates nearly enough rim pressure, and the Heat are 28th in three-point accuracy (24th since Feb. 9).
All of which is to say: Sitting out the trade deadline was certainly a choice—the wrong choice.
Miami shipped Dewayne Dedmon to San Antonio, and that was it, for some reason. This is not a team built for doing nothing, and it shows. Kevin Love was picked off the buyout market and is now starting games. The frontcourt rotation was and is so barren that Cody Zeller became a rotation regular before suffering a broken nose after spending most of the season on the outskirts of the NBA.
Much like every other squad on this list, the Heat were at the mercy of their limitations. They had future first-rounders to trade—up to three—but weren't flush with digestible salary-matching fodder.
Using Kyle Lowry (one year, $29.7 million) or Duncan Robinson (three years, $57.4 million) to anchor larger deals may have required forking over additional value to sweeten their contracts, and both Victor Oladipo (2023-24 player option; veto power) and Martin (two years, $13.9 million) are too important to move without deepening the rotation in the process.
Even something as ostensibly simple as reuniting with Jae Crowder was unnecessarily complicated. Step-laddering their way to his $10.2 million salary, like Milwaukee did, was virtually impossible.
There's still no need to give the Heat a pass just because they're theoretically thorny postseason participants as currently constructed or because they were only fit for bigger trades. Butler is 33, and Miami remains inside play-in territory with fewer than 10 games to play. You don't get bonus points for patience or playing it safe when you're built for urgency.
Portland Trail Blazers
5 of 5
The Regret: Wasting the best season of Damian Lillard's career.
Damian Lillard is averaging a career-high 32.2 points on a personal-best 57.2 percent shooting on twos to go along with a 37.3 percent clip from distance on 11.4 attempts per game. His assist percentage (34.6) ties another career high. He has never churned out a better free-throw-attempt rate (.460).
To call this the best season of his Hall of Fame-bound career would be accurate—and an understatement. His is an offensive performance of epic, historical proportions.
Among everyone to ever average at least 30 points per game, only three players have topped Lillard's current true shooting percentage (64.5): Stephen Curry (twice), Adrian Dantley and Joel Embiid (this season).
The Portland Trail Blazers' grand response to this season-long masterpiece? Effectively turning Josh Hart and Gary Payton II into Cam Reddish, Matisse Thybulle, Kevin Knox, a first-round pick in the 20s and a net of three second-rounders (five in; two out).
Woo-hoo?
Both Reddish and Thybulle have turned out to be potential keepers in advance of restricted free agency. Thybulle, in particular, looks more serviceable on offense than he ever did with the Philadelphia 76ers. Since arriving in Portland, he's moving more often and confidently toward the basket without the ball and hitting 39.1 percent of his 4.3 three-point attempts.
That doesn't make this an inspiring sequence of events. The Blazers were supposed to skirt another gap year because they have Lillard. Instead, they find themselves with a bottom-three Western Conference record that has left Dame calmly calling surrender.
Portland will be rewarded with somewhere between top-five-to-eight lottery odds for its raging incompetence. That's not nothing. Maybe the Blazers can turn some combination of that pick, New York's first, Anfernee Simons and Shaedon Sharpe into a co-star—preferably one who, at long last, stands taller than 6'3".
But this is not a team that can definitively outbid the field for players worth a damn. It owes a first-rounder to Chicago that's lottery protected through 2028, inherently limiting the amount of future draft equity it can send out. Retaining this year's pick goes a long way. Its value will also be debatable if it conveys outside the top four in what's considered a top-heavy class.
These same strictures offer the Blazers some cover here. Who were they supposed to get in this trade market without primetime draft assets to materially change this season's fortunes? I don't have an answer. That doesn't make any of this OK. Nor does another lottery pick guarantee a light at the end of the tunnel.
This is the best version of Lillard we've ever seen, and it's being wasted on a Western Conference nobody that actively sold at the deadline without doing much, if anything, to accelerate its position heading into next season.
Unless otherwise noted, stats courtesy of NBA.com, Basketball Reference, Stathead or Cleaning the Glass and accurate entering Tuesday's games. Salary information via Spotrac.
Dan Favale covers the NBA for Bleacher Report. Follow him on Twitter (@danfavale), and subscribe to the Hardwood Knocks podcast, co-hosted by Bleacher Report's Grant Hughes.
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