5. Signing Gary Payton II
The Warriors wanted to bring back Gary Payton II after their 2022 title run, but the team had to watch their spending. There was no second luxury tax apron at that point, but Golden State knew a massive tax bill was coming and every additional dollar meant spending significantly more than that.
The Blazers swooped in and signed Payton II to a three-year $26.1 million contract that the Dubs just could not match. Portland was excited about his defense and developing jump shot, but they overlooked his flaws.
GPII was approaching his 30th birthday and had played more than 30 games in an NBA season just once. Even in his breakout year with the Warriors, he averaged 17.6 minutes per game. The Trail Blazers were expecting him to play a key role, but Payton II was getting just 17.0 minutes a night before being traded back to Golden State just eight months after leaving.
The Portland Trail Blazers got five second-round draft picks and Kevin Knox in the four-team trade, which was a massive haul for a bench player that is making $8.7 million per year. Credit to Cronin for finding the right trade because the signing could have come back to bite the Blazers.