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The NBA offseason is supposed to generate optimism. Whether a team is rebuilding, positioning for a leap, or reinforcing a championship window, the summer months theoretically open every door. For five franchises this year, those doors led nowhere good.
Contenders who chose to get worse. Win-now mandates that produced reckless transactions. Organizational pivots with no destination. Failure to act when action was required. These are the categories that earn a spot on this list, and appearing here is never about a single move. Each team below produced a string of misfires despite having better options available.
A note on scope: the Golden State Warriors missing on LeBron James while Stephen Curry’s window closes is painful, but it wasn’t a correctable problem this summer. The same applies to the Sacramento Kings, whose past failures have left them structurally unable to tear things down. This list is about the mistakes and missed opportunities that were avoidable in the 2026 offseason.
Boston Celtics
None of the explanations offered for the Boston Celtics trading Jaylen Brown hold up under scrutiny.
They didn’t want to extend him? Brown had three guaranteed years remaining on his deal and zero leverage to force an extension or a trade. They wanted to reduce salary? They acquired someone making $3.7 million less who is more than five years older. They needed to move him before he became a net-negative asset? If that was the rationale, why accept Paul George and modest draft compensation instead of improving the offer for Giannis Antetokounmpo?
Accepting that this was the best return Boston could get is not the same as saying the trade was necessary. The Celtics could have retained Brown, repaired the relationship, and continued competing for Eastern Conference titles. Instead, they sold low, weakened their best playoff rotations, and are now banking on George’s expiring contract becoming useful trade currency next summer when packaged with picks.
Poaching Mitchell Robinson from the New York Knicks adds little shine to the offseason. Allocating 9 percent of the salary cap to a center who cannot exceed roughly 20 minutes per game or play both ends of back-to-backs is not a win.
Denver Nuggets
After a first-round exit, the Denver Nuggets decided it was prudent to release Peyton Watson without receiving any players in return. This marks the third consecutive offseason in which they have shed one of their six most important contributors to cut costs.
Blaming the second apron is a convenient deflection. Entering it for a year or two is not the organization-ending catastrophe ownership portrays it to be. It is also difficult to justify penny-pinching from an ownership group that just purchased MLB’s Los Angeles Angels at a $4 billion valuation, particularly when Denver is not yet clear of the second apron anyway.
The Nuggets may have a legitimate grievance that the core fell short against the Minnesota Timberwolves. But Watson’s four-year, $88 million deal averages 12.5 percent of the salary cap, which is fair value for his skill set. Smarter organizations pay that and sort out the rest later rather than prioritizing Cleveland’s 2031 first-round pick.
Denver might earn some grace if Nikola Jokić had signed an extension. For the second straight summer, he declined. Framing that as a delayed decision rather than a warning sign does not improve the Nuggets’ position. They have one of the three best players on the planet, in his prime, entering the final year of his contract, and they chose to make the team around him worse.
Los Angeles Lakers
The Los Angeles Lakers will likely finish third in the Western Conference next season. The process by which they restructured the roster only to remain clearly behind the Oklahoma City Thunder and San Antonio Spurs is what undermines the summer.
Four years and $129.5 million for Walker Kessler is defensible. Surrendering control of four first-round picks, two outright and two swaps, on top of that salary is not. Kessler’s fit alongside Luka Dončić is real, but the cost structure demands he reach Rudy Gobert-level defensive transcendence for Los Angeles to break even on the deal.
The “he was a restricted free agent and this is what it took” argument does not hold. The Lakers would have been better served reallocating those picks and that money across multiple contributors, at least one of whom is more than a minimum-contract wing.
Absorbing the Kessler opportunity cost would be manageable if Los Angeles executed every other move cleanly. It did not. Committing four guaranteed years to Sandro Mamukelashvili and Quentin Grimes while Mitchell Robinson received three guaranteed years and Norman Powell received one is difficult to explain. Handing player options to Mamukelashvili, Grimes, Austin Reaves, and Collin Sexton across the board compounds the problem. The Lakers will compete in the West next season, but this summer’s cap and asset allocation carries the potential to be remembered as the structural error that eventually pushes Dončić out of Los Angeles.
New Orleans Pelicans
The New Orleans Pelicans are more infuriating than the Kings because they are not helplessly stuck. They possess desirable players who could generate the assets needed to chart a real direction.
Bringing back DeAndre Jordan and taking a flier on Bennedict Mathurin that pushes the team into the luxury tax cannot be the primary offseason moves for a franchise that won 26 games. Even factoring in improved availability from Dejounte Murray and Herb Jones, this roster’s ceiling is “probably better than Sacramento.”
The roster’s internal contradictions are the bigger issue. New Orleans has too many big men and no legitimate defensive anchor at center. Developing Derik Queen and Jeremiah Fears properly is structurally impossible alongside Zion Williamson and a roster that lacks shooting. Shopping Zion, Herb Jones, Trey Murphy III, Saddiq Bey, and others should have been the summer’s central objective. Failing that, using existing assets to upgrade talent and roster fit would have at least indicated an intended direction. New Orleans cannot even gesture toward one at the moment.
Portland Trail Blazers
The Portland Trail Blazers entered the offseason with a clear need: shooting. They responded by trading for Ja Morant.
New owner Tom Dundon has already drawn attention for cutting corners on travel-party amenities and turning the head-coaching search into a public spectacle. Hiring Micah Nori to replace Tiago Splitter is justifiable on its merits. The one-minus-two deal Portland had him sign is not.
The Morant trade’s opportunity cost is acceptable in isolation. A flier on a soon-to-be 27-year-old is worth Jerami Grant and Kris Murray in a vacuum. The problem is that basketball does not exist in a vacuum. Even if Morant fully recovers his previous form, his fit in Portland is genuinely ambiguous. The team remains overloaded at guard even after the Shaedon Sharpe injury, and Morant’s play style offers limited flexibility. He has never cut off the ball with consistency and has not ranked above the 31st percentile in catch-and-shoot three-point efficiency since his rookie season, per BBall Index.
Read also: NBA Southwest Division 2026-27: Offseason Moves and Season Outlook for Every Team
Morant at full capacity also removes the ball from Deni Avdija’s hands and complicates the development of Scoot Henderson. Playing Morant alongside Damian Lillard creates predictable defensive liabilities. At a moment when the Blazers needed to consolidate and build on what worked last season, they have moved toward functional incoherence instead. Follow TipsGG for continued coverage as these rosters take shape heading into the new season.