4. Josh Hart trade
This trade may not look bad on paper. The Blazers got three players and a first-round pick in exchange for Hart one year after they acquired him in the CJ McCollum trade. This eventually became a four-team deal with the Matisse Thybulle trade lumped in. Portland gave up two second-round picks to get Thybulle, and none of the players they acquired from the Knicks remain on the team.
The first-round pick was used on Kris Murray, and it is too soon to say how that will work out.
Hart took his game to another level with the Knicks. He averaged 10.2 points, 7.0 rebounds, 3.6 assists, and 1.4 steals in 30.0 minutes per game and immediately helped them reach the second round of the playoffs.
Hart just got a four-year $81 million contract extension. That is massive money and more than Portland wanted to spend. Still, it feels like they should have got more than the 23rd overall pick for a player that is now making more than $20 million per year.
This was another key factor in the Damian Lillard trade request. The seven-time All-Star formed a tight bond with Hart during his year in Portland and the trade further proved the Blazers are not ready to contend.