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.