Celtics, Lakers and Nuggets Lead the NBA’s Biggest Offseason Regrets
GOATIFYEvery NBA offseason creates winners before a game is played. It also creates teams whose decisions become harder to explain the closer the season gets.
For 2026, five franchises stand out for different reasons. Boston moved Jaylen Brown and replaced him with an older, more expensive long-term question. Denver again sacrificed a major contributor while Nikola Jokic moved closer to the end of his contract. The Lakers improved their roster but paid an extraordinary asset price to do it. New Orleans still looks caught between competing timelines, while Portland added Ja Morant to a backcourt that already had more creators than clean fits.
None of that means these teams are doomed. The Lakers can still win a lot of games. Denver still employs one of the best players alive. Boston has talent. Portland’s Morant gamble could work. The issue is whether the choices made this summer gave each team the best chance to reach its actual goal.
Boston’s Jaylen Brown Trade Created More Questions Than It Solved
The Celtics’ summer can be reduced to one enormous question: why was moving Brown the best available path?
Brown still had three guaranteed years on his contract and did not possess the leverage of a player one season from free agency. Boston therefore did not have to make a rushed decision. It could have kept him, continued competing in the East and revisited the situation later if the relationship became unworkable.
Instead, the Celtics accepted Paul George and relatively modest draft compensation. George is more than six years older and did not create the dramatic financial reset that might have justified sacrificing a star in his prime. The move also weakened the type of two-way playoff lineup that helped make Boston so difficult to beat.
The argument that Brown’s value could deteriorate is possible, but it also cuts the other way. If Boston believed Brown was still a championship-level wing, keeping him through another strong season could have preserved or improved his trade value. If the Celtics wanted a transformational return, they could have continued exploring the market instead of treating this summer as a hard deadline.
Mitchell Robinson’s arrival adds size and rebounding, but it does not erase the central concern. Robinson has dealt with availability limitations and is not the kind of offensive piece who replaces what Brown provided. Boston may still have enough talent to remain dangerous, but the offseason lowered the margin for error.
Denver’s Peyton Watson Exit Looks Worse With Jokic Entering a Contract Year
Denver’s situation is less dramatic than Boston’s, but the pattern is becoming difficult to ignore. The Nuggets moved Peyton Watson without receiving a player back, continuing a run of offseasons in which important rotation talent has left while ownership tried to manage cost.
Watson was not a fringe piece. His four-year, $88 million contract with Cleveland reflects how the league values a young wing with his defensive tools and improving offensive game. Denver effectively decided the price was too high and prioritized future flexibility and draft value instead.
Second-apron restrictions are real, but so is the window created by Nikola Jokic. When a franchise has an MVP-level center in his prime, every decision to reduce the quality of the current rotation carries additional weight. Saving money is not automatically bad management. Saving money while the championship window is open is a much harder argument.
The pressure increased when Jokic declined an extension for the second consecutive summer. That does not mean he wants out, but it removes the comfort of a long runway. He is entering the final year of his current contract, and Denver now has to prove that its roster-building choices still match his competitive timeline.
The Nuggets remain dangerous because Jokic changes everything. But being dangerous is not the same as maximizing a championship opportunity. Losing useful players year after year eventually forces stars to compensate for weaknesses that used to be covered by depth.
The Lakers Got Better, but the Walker Kessler Price Was Enormous
The Lakers are the most complicated team on this list because the basketball fit is easy to understand. Walker Kessler gives Los Angeles a legitimate defensive center around Luka Doncic, and a four-year, $129.5 million contract is not outrageous for a player who can protect the rim, rebound and finish efficiently.
The concern is the total price. Los Angeles surrendered control of four first-round picks—two outright and two swaps—to complete the move. That kind of asset package changes the standard by which Kessler has to be judged. He does not simply need to be good. He needs to be good enough that the Lakers do not regret losing several future opportunities to reshape the roster.
The front office also handed out long guarantees and player-friendly terms elsewhere. Sandro Mamukelashvili and Quentin Grimes received four guaranteed years, while multiple contracts included player options. Each deal can be defended individually. Together they reduce flexibility around a core that may need another major adjustment later.
Los Angeles can still finish near the top of the Western Conference. Doncic is good enough to make almost any competent roster dangerous, and Kessler directly addresses a need. The issue is whether the Lakers spent too many future resources to solve one problem when a broader package of moves might have produced a more balanced roster.
This is the classic danger of win-now team building. A contender should be aggressive, but aggression only works when the asset cost leaves enough room for the next problem that appears.
New Orleans Still Has Talent Without a Clear Direction
The Pelicans’ problem is not a lack of recognizable talent. Zion Williamson, Herb Jones and Trey Murphy III all have real value. Younger players need development time. Veterans such as Dejounte Murray can help when healthy. The frustration comes from how difficult it is to identify one coherent direction connecting all of those pieces.
New Orleans brought back DeAndre Jordan and added Bennedict Mathurin in moves that push the roster toward the tax. Those are not meaningless additions, but they do not fully solve the structural problems that produced only 26 wins last season.
The frontcourt remains crowded without having a true defensive anchor at center. The offense still needs more shooting. Young players such as Derik Queen and Jeremiah Fears require developmental possessions, but those opportunities can conflict with a roster built around established veterans who also need the ball.
A more decisive offseason could have gone in either direction. New Orleans could have moved valuable veterans for picks and younger players, clearly committing to a reset. Or it could have spent aggressively on players who fit around Zion and Murphy, clearly committing to a playoff push. Instead, the team appears to have preserved much of the same ambiguity.
That is dangerous because middling teams can lose leverage over time. Valuable contracts become shorter. Young players become extension-eligible. Injuries change markets. The Pelicans still have enough talent to surprise people, but they also have fewer excuses if the roster again feels less than the sum of its parts.
Portland’s Ja Morant Gamble Could Work, but the Fit Is Awkward
In a vacuum, trading Jerami Grant and Kris Murray for Morant is easy to understand. Portland acquired a player who has already shown All-NBA-level ability without surrendering the kind of package normally required for a star.
Basketball is not played in a vacuum. The Trail Blazers already had a backcourt and wing ecosystem built around Deni Avdija, Scoot Henderson and eventually Damian Lillard. Shaedon Sharpe’s injury changes the short-term rotation, but it does not remove the long-term fit questions.
Morant is at his best with the ball. His speed and rim pressure bend defenses when he can attack gaps, manipulate pick-and-roll coverage and play downhill. He has never been an elite catch-and-shoot threat, which means simply moving him off the ball does not automatically preserve everyone else’s strengths.
Using Morant next to Lillard also creates obvious defensive concerns, while taking possessions away from Avdija and Henderson can slow the development of players Portland already viewed as central pieces. That does not make the trade a mistake by itself. Star talent is difficult to acquire, and teams often should accept some redundancy when the upside is high enough.
The issue is what comes next. Portland needs to build lineups that create shooting around Morant, preserve Avdija’s playmaking and keep Henderson on a development path. If the front office does not make follow-up adjustments, the roster could become a collection of interesting players rather than a coherent team.
That makes Portland the highest-variance member of this group. Boston and Denver can be criticized for giving up value. The Lakers can be criticized for overpaying. New Orleans can be criticized for indecision. Portland at least made a bold bet. The question is whether the fit work required after that bet was fully considered.
Why These Five Teams Will Be Judged Differently Once the Season Starts
Offseason grades are temporary. A move that looks reckless in September can become brilliant by May, and a decision that looks disciplined can become painfully passive if a contender falls short because it lacked one more player.
Boston’s evaluation depends on whether George can stay healthy and whether the Celtics can replace Brown’s two-way impact by committee. Denver’s depends on whether its supporting cast is deep enough to keep Jokic from carrying an unreasonable load. The Lakers need Kessler to become the defensive force they paid for, not merely a competent starter.
New Orleans needs to show that its collection of talent can finally produce a clear style and direction. Portland needs to turn Morant’s star upside into lineups that actually complement one another.
There is also a larger roster-building lesson connecting all five teams. The NBA’s cap system punishes expensive rosters, but the fear of tax and apron restrictions cannot become an excuse for wasting championship windows. At the same time, spending aggressively without valuing draft control can leave a team unable to react later. The best front offices know when to pay, when to wait and when to choose a direction before circumstances choose it for them.
That is why the 2026-27 season will be especially revealing for this group. These teams did not all make the same mistake. Some may not have made a mistake at all. But each enters the year with a specific offseason decision that will be impossible to ignore if the season goes wrong.
