Portland Trail Blazers Will Face Uncomfortable Questions This Offseason


The NBA regular season has reached crunch time, but for all intents and purposes, the Portland Trail Blazers’ year ended a long, long … agonizingly long time ago.

In a year designed to induce losses, the Blazers were still disappointments. The injuries were brutal. But becoming the first franchise to drop two games by at least 60 points in franchise history was embarrassing. And then losing by 60 again for a third time just 11 weeks later…there’s no better way to get kicked while you’re down.

Although brighter days are somewhere ahead, this was a rough year—no way around it. This summer won’t hold the same historical importance as 2023, but elephants will still be in the room as the doors open to the offseason.

Is Chauncey Billups Right for the Job?

Chauncey Billups has received a rotten hand in three years with the Blazers. Between legitimate injuries, tank-driven DNPs, multiple summers of Damian Lillard speculation, and finally a full rebuild, it’s been trying times for someone completing the third season of his head-coaching career (and currently coaching the league’s fourth-youngest roster).

With six games to go and sitting at 20 wins, Billups has plenty of excuses for falling under Vegas’ 28.5-win projection. But in reality, NBA coaching is unforgiving. And nobody is forgiving Billups for owning a .333 win percentage since 2021, especially when Years 1 and 2 became tankathons only after failing to compete on a meaningful level.

Whether Billups is relieved of his duties or not, the fact is this: Joe Cronin needs to speak on the matter. If the move is to trust the good he’s seen from Neil Olshey’s hire, everyone can commit to trusting the process.

If the front office, however, avoids a quick statement one way or the other, coaching fodder will continue feeding Rip City discourse, and the elephant in the room will only continue to grow bigger with time.

Is Anfernee Simons a Building Block or a Trade Chip?

Before the 2023-24 season began, I wrote about how Anfernee Simons wasn’t approaching the final stage of his evolution but instead entering Phase 1 as the nucleus of an NBA offense. That, of course, was to say Simons hasn’t even scraped his elevating ceiling. But it also proved ambitious in Year 1 of a rebuild, as the burden of running this team ultimately felt more like, well, a burden and less of an opportunity.

To this point, Simons’ improvement over 40-plus games played was modest. This year’s “leap” is better described as a hop and a skip, but his numbers did rise across the board, and he got a taste of what leading a young team is like.

The catch, of course, is that the NBA is a transaction-based business, and Simons’ name has been floated in trade rumors over the past few seasons. Similar to how we heard CJ McCollum’s name dropped before him, Ant has been in buzz involving hypothetical swaps for versatile wings. Cronin never pulled the trigger, choosing to trust in the post-CJ process. But after not being flipped for a Lillard co-star along the lines of OG Anunoby, Ant could still be shopped if he doesn’t project as a top option in Cronin’s eyes.

Important reminder here: Cronin didn’t draft Simons. With that in mind, he may not have the same motivation to see the six-year guard thrive in Portland as he may view Scoot Henderson or Shaedon Sharpe.

That’s not to say, of course, that Cronin wants Simons gone. But the truth is that Simons might be the Blazers’ best trade chip considering his age, potential and offensive fire power. And if the opportunity presents itself to move him for a better complement to Scoot and Shae Shae, Cronin could jump at it sooner rather than later.

Are Jerami Grant and Malcolm Brogdon Good as Gone? 

Cronin’s trade targets are impossible to predict, barring a gaze into that legendary moleskin journal. However, the general approach should include two predictable target archetypes right up top: future assets and potential building blocks.

At this stage in the rebuild, Cronin’s war chest already includes a few fun pieces. He has the Warriors’ 2024 potential lottery pick; gem pickups like Toumani Camara and Dalano Banton have real promise; and as discussed, Simons has at least one more level-up in him at just 24 years old.

All of these assets could be used to shape the future core—or they could individually (or collectively) be flipped in the near future for the right incoming piece.

Jerami Grant and Malcolm Brogdon are two players on the current roster who only fill the latter category and don’t project into the future.

Entering summer 2024, keeping one or both of Grant and Brogdon would be more palatable if the Blazers were anywhere near postseason contention. But that’s not the case. Everything about the team looks at least a year from that reality, and prioritizing those who influence the franchise identity is important to the level at which it might decide Cronin’s fate.

In short, Cronin has started the overhaul and can’t stop now because it’s nowhere near finished. This summer is about finally moving this team in a direction, and while drafting Scoot and trading Dame were the catalysts, they can’t be confused as the first actual steps. Those first steps are the ones Cronin is taking now that the dust has settled, and they’re the ones that will lead the Blazers in a clear-cut direction.

At least, that’s the hope in Rip City.

Pour one out for this season … and cheers to the future of Trail Blazers basketball.

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