Now comes the hard part (again)

Joe Cronin and Chauncey Billups have shown their strategic chops when it comes to tanking. But they still haven't shown that they can win. Or what their basketball beliefs are.

Instead of believing their team would find the form of their 10-4 start, the Trail Blazers front office saw it as the peak of what their team could be this season. Knowing when they’ve hit their peak seems to be the only organizational takeaway over the past two seasons. Other than tanking and projecting the image of a revamped front office working in collaboration, I’m not sure I know what they believe in.

The last time we spoke about this team at length, I was hypothesizing that the February trade deadline was having an adverse effect on the Blazers. Just about 10 days later, the Blazers decided that the best way to deal with it was to A) nab the No. 23 pick in the 2023 draft for Josh Hart, who they were not going to bring back long-term, and B) cut bait with Gary Payton II, who will go down with one of the most bizarre tenures in Blazers history.

They know how to cut bait and they’ve accumulated assets. But as we’ve seen before, assets are only one part of the equation. As the 3 first-round picks in the 2017 Draft can show us, assets are nothing if you make the wrong bets. And the Blazers’ front office decided to cash out for more chips, biding their time for the bet of their lives to put a contender around Damian Lillard.

For as nice as it was to see Matisse Thybulle have more confidence in his 3-pointers than Hart, trading two veteran players for Thyblle, Cam Reddish and a parade of 10-days, Cronin and the front office made the decision to be worse by rostering younger players to secure a 10.5% chance at drafting generational French prospect Victor Wembanyama. Which, in large part, was simply a continuation of what happened last season following the internal investigation that led to Neil Olshey’s firing.

But as someone who is keen on discerning the difference between building a winner and building job security for NBA executives, I remain in need of convincing from the new regime. The honeymoon period is over. For as freeing as the departure of Olshey was, so too was the power vacuum left by him chaotic. And while we all generally like the heads on the shoulders of Cronin and the front office, the vibes are no longer enough on their own.

And even if the dream scenario of drafting Victor Wembanyama came to pass, the pressure to win will only increase with a player compared to the likes of Kareem Abdul-Jabbar or Wilt Chamberlain. There is no waiting when those guys arrive. The Process will have come to fruition. The show will be on, even as this front office has worked hard to avoid being on the clock.

My Wemby/Dame Vision Board

Lillard’s comments at exit interviews put all of this into focus on Sunday. He can’t wait anymore. And frankly, after two tanking seasons, neither should the fans.

Chauncey Billups was adamant that he wants to show how much he’s grown as a coach, particularly with a veteran group that he desires. The way the rag-tag group of young players responded to him shows that he does have the ability to motivate a young group.

So now what do we make of Billups’ long-stated desire to coach veterans with his short record of having coached them? Short as it is, it’s all we have to judge those claims, and Round 1 wasn’t very good. He HAD a veteran group to start the 2021-22 season, chaotic as it was. Judging by the deterioration of his relationship with Robert Covington towards the end of Covington’s tenure, the evidence that Billups will coach better hangs by a thread because of Lillard’s belief in him. The actual practice of coaching other veterans who are not Dame didn’t go too well.

Regardless of what Billups or Cronin said, things have got to get more serious around here and any thinking person watching the last two years will have a hard time believing that they will just get some Vets and fix it. Cronin is a serious person, but he’s got a lot to manage, particularly his relationship with Billups, whose familiarity with Cronin is a factor in his hiring that cannot be ignored.

With all of that said, I have a bit of a concern that vibes have outweighed establishing a serious winning culture. Billups was brought in, in large part, to improve the defense. They’ve maintained a bottom-five ranking and have lost the offensive juice of the Stotts teams. So they’ve gotten worse. The Blazers play more zone and they switch more often, but the defense still sucks. Save for Scott Brooks, whose expertise is more in player development than strategy, the coaching staff next to Billups, which includes his younger brother, is light on experience. All of these are things that need to be addressed.

In terms of offensive and defensive principles, I saw a team that let their opponent’s strengths dictate the rules of engagement rather than a team that had a real identity. The Stotts era may have been too sturdy in its basketball principles, but the Billups era squads feel like an exercise in micromanagement.

Whereas the Olshey era over-indexed on paranoia and maniacal control, it does feel as though the current regime is too concerned about sharing with the public how collaborative they are. How welcoming it is. While I think it’s great that the Blazers have revamped their front office and I also like the changes on a personal level, the only tangible takeaway from the current regime is that they understand when their team isn’t good enough, unlike the tail end of the Olshey years, which featured sending another future first-round pick out for a role player to kick the can down the road.

The current regime has been paying for those sins, but those debts to the devil are things every front office has to deal with. The next task, the real task that will dictate how they all will be judged as basketball people for their entire careers, is one they have yet to accomplish. Can they build a team that actually is good enough?

I like the personalities of this Blazers front office and how they do business, but when it’s time to be judged by winning, as they will be moving forward, can they prove they’re a serious group and not more than a well-executed exercise in leadership marketing? Other than knowing when it’s time to lose, I still don’t know what this group’s basketball principles are beyond “we like good players.” So does everyone else. What kind of players are they looking for? How do they want to play? I still don’t know.

Perhaps it’s unfair to say they have no principles. We know that Dame is part of those principles, but how about the players around him? What about how to use him? Billups basically had to be convinced to let Dame run heavy pick and rolls midseason due to some unsavory droughts, but still left so many other great options for Dame to eat on the buffet line. Dame can work well off the ball, but how he was used off the ball left a lot to be desired. I can’t imagine that Dame doesn’t feel like he knows he could have had an even better season, even if this season was his best statistical one to date.

The Blazers, confusingly, averaged fewer dribble-handoffs per game this season than last, despite having Dame for far more games, per NBA stats. The DHO is a key action that Terry Stotts employed, which Dame has used to great advantage his entire career. But it was used much less this season despite its effectiveness.

The Blazers failed to lean on that action as much as they should, despite jumping up from 0.9 points per possession on those shots to 1.08, the highest rate in the league, which can mostly be credited to Lillard’s return to health. However, their frequency paled in comparison to league-leader Sacramento, who generally have better spacing and a more sophisticated offensive attack. Something, the Blazers didn’t really display much. It’s only one type of play, but to me, it’s indicative of a coaching staff that might not know yet how to maximize their best player. Two years in, that’s a major concern.

Cronin spoke about his anxiousness to push the Blazers chips in and I believe him. A Wemby miracle would help the Blazers position to make deals.

But just like Dame, I’m waiting to see. Not be told.