6. Evan Turner contract
If two nightmare moves in the 2016 offseason were not enough, the Blazers made a third when they gave Turner a four-year $70 million contract in free agency. The deal made him the 47th highest-paid player in 2016-17. Turner earned more than Stephen Curry, Draymond Green, Gordon Hayward, and Kyle Lowry, who were all All-Stars in 2017.
Turner averaged 9.0 points, 3.8 rebounds, and 3.0 assists in 25.5 minutes per game. It was a significant step backward from the previous season and turned out to be his best year in Portland. The Blazers did reach the conference finals in 2019 with Turner playing a 15-minute per-game role off the bench, but he was not a clear fit in a league that valued floor space more than ever.
Portland traded Turner to the Hawks for Kent Bazemore in 2019, and he lasted just one more year in the league before retiring in 2020. Bazemore was traded to the Kings in Jan. of 2020, but the Trail Blazers were happy to clear Turner’s contract off their books.
Joe Cronin was the Director of Player Personnel for all of the moves so far. He had a hand in them but was not the Portland Trail Blazers lead executive. Since taking over in 2021, he has made his fair share of regrettable moves and the top five will detail the worst ones.