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. That’s manageable when both players are healthy, but there’s almost no margin for error. Head coach Terry Stotts is already all but obligated to stagger their minutes, limiting his rotation options, and if either player misses time the point guard position becomes a major question mark.

Anfernee Simons and Mario Hezonja were the two players expected to fill the role of third playmaker before the start of last season, but neither showed consistent competence in that area during the regular season. Adding a veteran point guard as an insurance policy should be viewed as a necessity to fill this gap.

Combo Big Man

Similar to the backup playmaker role, the Blazers theoretically have the pieces to fill the 4/5 rotation on a nightly basis, but reality has been a little bit different. Jusuf Nurkic and Hassan Whiteside are both traditional centers and playing them simultaneously almost certainly will not work in many matchups. Zach Collins has shown promise but it’s still unclear if he can handle major minutes as a primary 4/5 option. Ideally, Portland will find a mobile big man this summer who can play both positions to supplement the rotation in games that Nurkic or Whiteside are not viable due to match-ups or when Collins is inevitably in foul trouble.

3&D wing

The Blazers actually have several floor-spacing wings, but question marks surround nearly all of them. At 35 years old Trevor Ariza’s skills will inevitably decline sooner rather than later, Rodney Hood’s effectiveness is still TBD as he recovers from a torn Achilles, and Carmelo Anthony’s defense is ...suspect. That leaves Gary Trent as the only competent defender who can space the floor next season. And even he is undersized to match up with the likes of LeBron James and Kawhi Leonard. The need for an upgrade at this position is almost self-explanatory.

Bottom Line

The breadth of Portland’s roster needs is reflective of a general lack of depth. One could argue that Lillard, McCollum, Nurkic, and Trent are the only players on the team guaranteed to fill their expected roles next season. After accounting for Hood’s possibly career altering injury, Ariza’s age, Whiteside’s contract status, and Anthony’s contract status and age, the roster is stacked with more question marks than a Super Mario level. The bottom line is that it will be very difficult to fill out this roster.

What’s interesting, however, is that Olshey seems to recognize these limitations and has tried to address them as efficiently as possible in the past but failed in actual execution. The preseason fan fantasies of Mario Hezonja or Evan Turner are examples of fundamentally flawed players who can, nevertheless, fill multiple roster holes — in this case backup playmaking and range/size on defense. Similarly, Anthony Tolliver circa 2015 (with his video game sliders juiced up by 20 percent) would be a solid backup big man. He’d be able to guard the 4 or 5 and provide spacing for Lillard, McCollum.

The positive spin here is that, overall, the theory of roster building the Blazers have strategized in the past few years will fill the holes of the current roster. Now the question is whether or not Olshey can turn that theory into practice and acquire players who provide more than question marks and deep bench fodder.