Predicting the 5 Biggest Regrets From the 2026 NBA Offseason

Craziest NBA offseason ever?

The 2026 version can certainly make its case.

Whether it be LeBron James signing a veteran minimum deal with the Philadelphia 76ers, Giannis Antetokounmpo leaving the Milwaukee Bucks after 13 years, the shocking Jaylen Brown-Paul George trade or any other of the big names now in a new location (LaMelo Ball! Ja Morant! Probably Kawhi Leonard!), our heads are still spinning with transactional satisfaction.

Of course, not all of these moves will work out for the best.

Whether it be some questionable contracts handed out, overpriced sign-and-trade deals or superstar blockbusters, these five moves will end up as some of the biggest regrets for teams and players when looking back at the summer of 2026.

Wizards Giving Trae Young $53.2 Million Per Year

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In a deal that was probably worked out before his trade from the Atlanta Hawks, the Washington Wizards officially gave Trae Young a four-year, $212.8 million contract. The deal also includes a player option in the final year and a 7.5 percent trade kicker.

This was the max offer Young could have received from any other outside team, although no franchise was giving the 27-year-old point guard this kind of cash.

Young is probably the worst defensive player in the NBA. He's 164 pounds and regularly gets hunted by opponents at every opportunity. While a gifted passer and offensive threat, Young owns career shooting marks of just 43.3 percent overall and 35.2 percent from three.

The Hawks went 2-8 with Young in the lineup this season, then truly took off after trading him away. A 44-28 record without Young for Atlanta should have been reason for the Wizards to pause on a new contract.

Washington's desperation to return to relevancy by giving Young a 30 percent max deal and trading for Anthony Davis was both foolish and shortsighted, especially if they give the latter a massive extension as well.

Outside of passing, Young has no All-Star level skills and is the biggest defensive target in the league. Giving him $200 million will not age well.

Celtics Trading Jaylen Brown for Paul George, Picks

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Jaylen Brown getting traded wasn't a surprise.

The 2024 Finals MVP being moved for arguably the worst contract in the NBA, two first-round picks/swaps and two second-round picks while his value should have been at an all-time high was the shock of the 2026 offseason, however.

Getting the Shams Charania notification seemed like a mistake. Surely he forgot to include something, right? VJ Edgecombe? Two more first-rounders? The Rocky statue?

This was the worst trade in the NBA since Luka Dončić.

Paul George is owed $54.1 million this season and has a $56.6 million player option in 2027-28 when he'll be 37 years old. He's averaged just 16.7 points on 43.4 percent shooting since signing with the Philadelphia 76ers while playing a total of 78 games in two years due to injury and a suspension.

Brown is compensated extremely well, but is set to make just $3.6 million more than George this season. This wasn't a salary dump, and the draft equity coming back is underwhelming.

There was talk for years that the Boston Celtics would eventually break up the Jayson Tatum-Brown combo, although that was quieted following the 2024 title. Why Brad Stevens chose this time and this package for a trade doesn't make any sense.

A core of Tatum, George, Derrick White (32) and Payton Pritchard isn't title worthy, not in an improved East. Boston will be fighting just to get homecourt advantage in the first round, with championship dreams all but out the window following this atrocious trade.

Lakers Investing $130 Million Plus 4 1st-Round Picks and Swaps in Walker Kessler

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Walker Kessler is a strong basketball fit alongside Luka Dončić and Austin Reaves. The Los Angeles Lakers also paid far too great a price for the 7'2" center and as a result are now locked into a mediocre roster in the West.

The Lakers and Utah Jazz agreed to a sign-and-trade that sent Kessler to LA, with the 25-year-old inking a four-year, $129.5 million contract. This part is perfectly fine, even though it includes a player option in the final year and a 15 percent trade kicker. If Kessler is healthy, investing 18 percent of the cap (around $32 million per year) is a deal that should make both sides happy.

The problem lies in the draft compensation, an area the Lakers were already running short in. Los Angeles previously traded away their first-round picks in 2027 and 2029. To get Kessler, Rob Pelinka and company agreed to give the Jazz unprotected firsts in 2031 and 2033.

That wasn't all, however.

As if two future unprotected firsts weren't enough (already more than the Philadelphia 76ers had to give up for Jaylen Brown), Utah also gets first-round swap rights with the Lakers in 2028 and 2030. This means that the only draft compensation LA has left is a 2032 first-round pick swap and three future second-rounders.

If the Big 3 of Dončić, Reaves and Kessler isn't enough to get by the Oklahoma City Thunder, San Antonio Spurs and the rest of the West (it won't be), Pelinka is out of draft picks to improve the team.

This is the kind of price a team pays for an All-Star center in their prime, not a career part-time starter who played just five games last year after tearing a labrum.

Given their cap space, the Lakers should have chased an unrestricted free agent like Isaiah Hartenstein, Mitchell Robinson or Robert Williams III, all of whom signed far cheaper deals and wouldn't have cost LA any future draft capital.

The Giannis Antetokounmpo Trade (for Miami and Milwaukee)

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Everything about the Giannis Antetokounmpo trade feels wrong.

The timing is wrong, as the Milwaukee Bucks should have ripped off the band-aid and dealt the two-time MVP last summer. Now, the franchise is stuck with $90 million worth of dead money from Damian Lillard's contract and Myles Turner's deal. Moving off of him and clearing a runway for Kel'el Ware is the best path.

It feels wrong for the Miami Heat, who had to gut the roster for a star who's already entering Year 14 and is six seasons removed from his last MVP. Calf injuries are piling up for Antetokounmpo, who was limited to just 36 games last season and hasn't made it healthy and out of the first round of the playoffs since 2022.

It feels wrong for Antetokounmpo and his legacy, especially after tweeting out stuff like this just a few months ago when we all knew this day was coming soon.

The way Miami has attacked the rest of their offseason feels wrong as well.

Losing Norman Powell in free agency isn't talked about enough. An ideal shooting guard to put in a lineup with Antetokounmpo and Bam Adebayo who made the All-Star team last season, Powell left the Heat for the Chicago Bulls in search of a bigger payday, but did he have to?

Miami hardcapped itself at the first apron with how the trade for Antetokounmpo and Bobby Portis was structured. Working out a new, long-term deal for Andrew Wiggins could have created space for Powell to return, although the Heat extended him on a two-year, $33.8 million deal instead.

Wiggins will play this season on a $30.1 million player option, although opting out and signing a new three-year, $63.8 million deal would have guaranteed the wing the same amount of money while opening up roughly $10 million to help re-sign Powell.

Losing Powell in free agency along with trading Tyler Herro, Ware, Jaime Jaquez Jr., Kasparas Jakučionis, three first-round picks and additional draft equity is a hefty price to pay for someone who has real durability concerns and is on the back nine of their career.

The Bucks should already regret making the Antetokounmpo deal when they did. There's a real chance Miami will regret it as well.

LeBron James Choosing 76ers

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LeBron James signing with the Philadelphia 76ers still doesn't feel right. It's also a move he's going to end up regretting.

There's no questioning the amount of talent on this team. Jaylen Brown is a massive upgrade over Paul George. Joel Embiid is one of the league's most unstoppable forces when he's on the court, and Tyrese Maxey is coming off an All-NBA season.

Outside of Maxey, the rest of this roster contains too many question marks for James to spend the final year(s) of his career tied to, however.

Embiid has played 38, 19 and 39 games in each of the last three regular seasons. He was again hurt to begin the 2026 playoffs, had four good enough games to help take down the Boston Celtics, then ran out of gas in the second round against the New York Knicks in a sweep. Is there any reason to believe the 32-year-old can actually make it upright through two months and four grueling rounds?

The idea of Embiid has far outpaced his actual production in recent years, and his contract (an average of $62.4 million over the next three years) may be the worst in the NBA.

James and Brown are a terrible fit as well. The 2024 Finals MVP finished second in the NBA in usage rate (36.2 percent) and shot attempts per game (21.7), so he needs the ball in his hands. Reducing James to a 3-and-D option (who no longer plays regular-season defense) is a waste of his talents, especially with Embiid and Maxey needing their touches as well.

James would have been a far better fit in places like Cleveland and Golden State, or even in Miami where teams had more durable stars around him and/or a cleaner offensive role.

Adding yet another new team to the end of his career typically doesn't help a player's legacy, as visions of Michael Jordan with the Washington Wizards or Shaquille O'Neal in Boston Celtics' green have become major eye sores.

Winning with the 76ers would undoubtedly be a legacy boost, although a poor fit combined with Embiid's lack of durability will ultimately doom any chance of a title for James to end his career.