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What hole in the roster should the Trail Blazers fill first?

The Trail Blazers roster needs an upgrade (or three) this offseason. After a Cinderella run to the 2019 Western Conference Finals, General manager Neil Olshey fortified the team’s bench with Mario Hezonja, Anthony Tolliver, and Hassan Whiteside. The results were not great — the Blazers struggled to even make the playoffs this season and various holes in the roster were exposed by the Lakers in a first round shellacking.

With that backdrop, let’s consider three needs Olshey must address this offseason:

Backup Playmaker

Damian Lillard and CJ McCollum are the only two Blazers who can reliably initiate the offense right now.