2. Anfernee Simons
Blazers fans seem divided about what they'd like the team to do with Simons. Besides playing remarkably similar to arguably the greatest Blazers player of all time, Damian Lillard, there are valid reasons for wanting to keep Simons around. For one, he's still only 24 years old and will be entering his prime by the time the Blazers hopefully reap the benefits of their rebuilding process. He's also the team's best shooter, an area they desperately need help in.
On the surface, it doesn't make much sense to get rid of a 24-year-old guard who just averaged 22.6 points and 5.5 assists while shooting 38.5 percent from three. However, the problem isn't necessarily with Simons. It's simply about the Blazers' roster construction, which could cause Simons to be the odd man out.
The Blazers plan on having former No. 3 overall pick Scoot Henderson as their franchise point guard, despite his relatively shaky start to his NBA career in his rookie season. Although a great shooter, Simons is a giant defensive liability due to his 6-foot-3, 193-pound frame. Henderson is also 6-foot-3, meaning that backcourt can't coexist effectively long-term, at least from a defensive standpoint.
With the amount of physicality in the playoffs and the NBA superstars who are so well-versed in taking advantage of size mismatches, the Blazers' best option in the long term may be to get rid of one of their best players.
Per Sean Highkin of the Rose Garden Report, Simons wants to have the opportunity to win soon. Simons has been great for Portland, but both parties may benefit from a change of scenery.