5. Dennis Smith Jr.
Dennis Smith Jr. is slowly turning into an NBA journeyman. Despite being 26, he's already played for six teams. As the No. 9 overall pick in the 2017 NBA Draft out of NC State, Smith showed a lot of promise in his rookie season with the Mavericks, averaging 15.2 points, 5.2 assists, 3.8 rebounds, and one steal a game. His aggressive, downhill-attacking style of play at NC State, which made him a lottery pick, translated well at the beginning of his stint with Dallas.
Unfortunately, Smith Jr. hasn't been the same player since his rookie year and has yet to find his right landing spot. He was limited to 37 games with the Blazers in the 2021-22 season. Portland could technically give Smith Jr. another chance in free agency this summer, but there are some question marks regarding his fit.
As of now, the Blazers have a massive log jam at guard position. But even if it clears up and Portland trades one of Malcolm Brogdon or Anfernee Simons, Smith's skill set is pretty redundant to that of Scoot Henderson's. Both are inefficient, undersized guards who aren't great shooters at this stage in their respective careers. Both of their strengths are as highly athletic and are great at putting pressure on defenses when they attack the paint.
If the Blazers add another guard in free agency, it would make more sense to bring in someone who can better complement Henderson and Shaedon Sharpe's athleticism with their ability to space the floor.