How Bad Will It Get for the Blazers?

This season is the most dismal Blazers fans have experienced since Zach Randolph roamed the hardwood. The team comes out of the All-Star break with no All-Stars and a putrid 15-39 record. The most alarming possibility, however, is that the worst is yet to come. We asked two lifelong Blazer fans and occasional WW analysts to poke at the sore spots.

WW: Does head coach Chauncey Billups know what he’s doing?

Bob: There hasn’t been much evidence that Chauncey Billups can be the coach of a winning basketball team, but that isn’t really his job anymore. For the back half of the past two seasons and all of this one, his job has been to develop the organization’s prized young players, the main trio of whom—Shaedon Sharpe (age 20), Scoot Henderson (20) and Anfernee Simons (24)—didn’t play college basketball. Billups has been better at his new job than he was at his old one.

Eric: I agree. The most important thing for Billups, and the franchise as a whole, is that some portion of the Simons-Henderson-Sharpe trio develop into All-Stars. How much of that development truly falls to the head coach? Hard to say. What we do know, so far, is that if you’re handing out grades to Billups’ guards, they look something like a C for Henderson, an A on offense and D on defense for Simons, and an Incomplete for Sharpe. Not ideal. Possibly a big enough problem it eventually leads to a coaching change.

On the flip side, several long-shot bench prospects have excelled, relative to expectations, so if Billups takes any lumps for the underwhelming backcourt, he also deserves credit for developing the role players.

Outside of player development, if we are looking for positives, from the fan perspective, Billups’ high-pressure defensive game plan is a lot of fun to watch when it is clicking. A polar opposite to the risk-averse game plan of Terry Stotts. Billups has also found some unexpectedly successful combinations of players—in particular, the frontcourt of Grant, Jabari Walker and Ayton seems to have good chemistry.

Is Scoot Henderson actually good? Was he worth losing Dame for?

Bob: The problem for young Sterling “Scoot” Henderson is that he will be inextricably linked to Lillard for the rest of his career. The latter question will be answered by whether Scoot becomes a player equal to or better than Lillard, who will be in the Hall of Fame someday. It’s also impossible to answer.

As far as the former, I think Scoot had a bad handful of games at the very start of his career as a teenager learning the game’s most difficult position and has been rather good and remarkably poised since.

Eric: I’m going to be a contrarian here and argue that Scoot doesn’t have to be linked to Lillard. Yes, it’s true that Lillard was traded shortly after Scoot was drafted. But that trade was a long time coming. Rumors that Lillard may be headed “out the door” date back to summer 2021. Instead of asking if Scoot was worth losing Lillard, I would ask if the rebuild we are all living through was worth losing Lillard.

And, so far, we don’t have a clear answer. The alternative to the rebuild, discussed ad infinitum at the time, was to trade the pick that became Scoot for an All-Star. Let’s roll the dice that adding Pascal Siakam, for example, to Lillard, Grant and Simons could have kept Dame satisfied. Would that team have competed for a championship? The Pacers aren’t exactly generating championship buzz after adding Siakam at the trade deadline to their own top-tier offense helmed by two-time All-Star Tyrese Haliburton. Hard to imagine the Blazers would have had significantly more success. Siakam, or a similar player, would have helped the Blazers stay playoff-relevant, but probably not championship-relevant.

Of course, playoff-relevant is going to look pretty damn good in a couple of years if the Blazers continue floundering to 20-something wins. But keep this in mind: General manager Joe Cronin and his staff have a mountain of assets at their disposal to expedite the rebuild. Solid veterans (Ayton, Grant and Matisse Thybulle), blue-chip prospects (Sharpe and Henderson), an up-and-coming flamethrower (Simons), multiple competent bench players, and two first-round picks in the upcoming draft. If Portland’s front office can’t figure out how to turn all of that into a winning team in the next year or two, what are the odds they could have built a contender around Lillard in his final few years as an All-Star?

We’re all at least a little worried about if and when Scoot is going to put it together. But how do we feel about Sharpe right now?

Eric: Ideally, Sharpe would have taken a leap this season. He is relentlessly exciting in the open court and has shown surprising patience for a young player. But his development seemed to stall—Sharpe certainly has not kept up with fellow 2022 draft classmates like Paolo Banchero, Chet Holmgren and Jalen Williams. Some of that has been injury-related. Sharpe has played in only 32 of 54 games at the All-Star break. But some of it seems to be his fit with the roster/coaching. The Blazers offense feeds the ball-dominant creators like Simons, Brogdon, Grant and Henderson. Sharpe either needs to continue working on impacting the offense while playing off those creators, or the coaching staff needs to create more opportunities for him.

Bob: Kobe Bryant once said that Brandon Roy was the most difficult one of his contemporaries to guard: “365 days, seven days a week. Roy has no weaknesses in his game.” As far as natural talent and the capacity to become a truly complete player, Sharpe is the closest thing the team has found to Brandon Roy since he walked away 13 years ago. It’s also important to remember how few actual basketball games Sharpe played in as a teenager, between the pandemic and not playing while at Kentucky. Be patient. There’s a pot of gold at the end of the rainbow.

Is the team going to be sold or moved?

Bob: Because of what happened in Seattle (and in Vancouver, B.C., a few years earlier), Commissioner Adam Silver and the league’s power structure will do anything necessary to ensure that the Blazers don’t become the third NBA franchise to leave the Pacific Northwest since 2001. Silver understands the importance of franchise stability to the league’s future and, while deputy commissioner, was the main catalyst for the Kings staying in Sacramento. He also happened to be a congressional intern at the same time as his friend and one of Oregon’s most powerful people, U.S. Sen. Ron Wyden. Everything is probably going to be OK.

Eric: The Blazers are currently owned by the late Paul Allen’s estate. It’s been well-publicized that the franchise will be sold “within a reasonable time frame,” per the instructions Allen left for the estate when he passed away five years ago. The definition of “reasonable time frame” remains unclear. NBA Commissioner Adam Silver does not seem inclined to force a sale any time soon, based on public comments.

Read our cover story: Blazers tickets are $2. Here’s who you’ll sit with.

Once news of a sale does break, the city should be prepared for team ownership to look different from past eras. Since the franchise’s founding in 1970, the Blazers have been owned by West Coast business magnates—Allen most recently, and Larry Weinberg before him. But franchise ownership in the NBA has increasingly gone the way of private equity in recent years. Now they’re allowing “sovereign wealth funds,” pension funds, and endowments to buy shares.

What does that mean for the Blazers? Unless Phil Knight has another offer in his back pocket, it’s increasingly likely the team will be sold to an entity (entities?) that has fewer personal connections to the team and city than past owners. Will those owners be willing to pay the luxury tax? Will they try to convince the city to finance a new arena or other infrastructure? Will they sell a minority stake to Damian Lillard? The long-term consequences of a sale remain unclear.

Is Ayton really a spiritual successor to Hassan Whiteside, as The Athletic’s Jason Quick posited in a recent column?

Bob: Ayton and Whiteside are similar in that both, when engaged, could single-handedly dominate NBA games on both ends of the floor. However, whereas Whiteside just didn’t really seem to care about basketball, Ayton’s problems seem to stem from insecurity and ego, which in theory can be fixed. At his introductory press conference, he referred to himself as “DominAyton.” To this point, he can more reasonably be referred to as ParticipAyton. He needs to be able to be more consistent if he’s going to be a part of the team going forward.

Eric: Ayton certainly did himself no favors with the DominAyton moniker. But I bristle at the comparison to Whiteside. Whiteside earned the levied criticisms largely by racking up “empty stats.” He would sniff out uncontested rebounds and chase blocks instead of playing team defense. Leading the league in blocks looks great on paper, less great when you look at the tape and see how often he was out of position, ceding easy interior assists.

Ayton, in contrast, has largely been criticized for a perceived lack of impact. It’s easy to see his two-way athleticism and imagine Ayton competing with Bam Adebayo for All-Star honors. Focusing on Ayton’s hypothetical impact, however, overlooks the very real impact he does have. Yes, he frequently fails to challenge midrange shots and could be more assertive with his post moves, but he is still a solid starting center, averaging a double-double and providing points around the rim.

Ayton also benefited significantly from playing with Chris Paul and Devin Booker in Phoenix. Their passing and gravity, respectively, created lots of space for Ayton to exploit. The Blazers have not had great spacing this season. If and when the offensive cohesion improves, Ayton should be able to help his backcourt teammates exploit rotating defenses. We got a preview of what that might look like against the 76ers on Jan. 29, when Ayton scored eight layups or dunks, all assisted by a Blazers guard.

Which of the players will still be on the team in a year or two?

Eric: The ultimate reality is that the Blazers are right up against the luxury tax for the 2024-25 season but at the bottom of the standings. Some of these players will be headed out soon.

Rookie contracts are worth their weight in chalupas. They lock young prospects into a relatively affordable four-year deal and give the incumbent team a leg up in negotiations for the next contract. Shaedon Sharpe and Scoot Henderson aren’t going anywhere until at least summer 2025 (barring a roster-tilting superstar trade).

One of the bright spots so far this season has been the success of Toumani Camara, Jabari Walker and Duop Reath. Those three seem likely to stick around—Camara and Reath are already signed through 2026.

Beyond those five, it gets tricky. Malcolm Brogdon is the obvious trade candidate, but both the team and Brogdon have been positive about their relationship. Could he stick around as a third guard in the event that one of Anfernee Simons, Sharpe or Henderson is eventually traded for an upgrade in the frontcourt? Do Jerami Grant and DeAndre Ayton fit the timeline and style of the rest of the roster? Will Kris Murray or Rayan Rupert impress as we enter the tail end of the season?

Bob: Just based off high-level stuff like age and positional fit, my best guess re: list of keepers would look something like Scoot, Sharpe and whichever of the young wings turn out to be able to shoot. My hunch is that Rupert will be the team’s long-term answer at small forward.

Eventually, some team is going to convince themselves that Jerami Grant is the missing piece between them and a championship. The Blazers should be able to return a good amount of value for Grant and the other veterans—particularly Simons if they decide he can’t coexist with Scoot.

I would also like for Duop Reath to be on the team forever.

Cronin has said the Blazers want to be competitive again sooner rather than later. Given that assumption, what is a reasonable goal for next year?

Bob: If they bring back their current players—and all of them play as well as you could reasonably hope—they could be a .500 team and spend most of the season in the play-in tournament hunt. If Sharpe takes a quantum leap, which is very possible, they could be something more. But my best guess is that they’ll win something like 35 games.

Eric: Cronin and his staff have employed a solid process thus far. If one accepts that trading Lillard was inevitable, it’s hard to find many faults with decisions that Cronin is making. They’ve drafted two high-upside lottery prospects, swapped out Jusuf Nurkic for Ayton, resisted trading low on Grant (or Brogdon), identified diamond-in-the-rough role players for the bench, and have multiple extra draft picks in coming years. In principle, that’s a solid rebuilding process!

Eventually, however, Cronin’s process must turn into results. Twenty diamond-in-the-rough role players can’t make up for a lack of All-Star talent at the head of the roster. My hope, similar to Bob’s, is that the team shows positive growth next season and finishes with a win total in the mid-30s. Anything less than that and it’s a sign that a key component of the rebuild has already broken.