MAILBAG (PART 1): Rookie Scoot vs. Rookie Dame, Expectations for Chauncey Billups and Other Trail Blazers Topics

Answering subscriber questions in the first part of a new mailbag.

A week ago, I put out a call for Trail Blazers mailbag questions with one stipulation: let's try to keep it away from Damian Lillard's trade request, because there's nothing new to say about it and I'm tired of talking about it.

I wasn't sure how that was going to go, but it turns out, there's plenty of other stuff to talk about. I got so many good non-Lillard questions, in fact, that we're going to split it up into two parts, with the other one running later in the week.

As always, the questions came from paid subscribers. Part one today will be free to everyone; the second part that's coming out in a few days will be for paid subscribers only. If you want to read that, or participate in future mailbags, hit the link below.

Hi Sean,

I am curious what your thoughts are now with the shift to more of a rebuilding/youth movement if Chauncey has a maybe a more opportune chance to showcase his coaching style? I feel like the offloading of contracts in year one and the two timelines thing in year 2 has in a way limited what he’s been able to implement because of the inconsistencies of the roster. Assuming the dust settles before the start of the season, do you think this year (wins/losses aside) will be a better assessment for the fans and those covering the team of whether he has the coaching chops to move forward and develop with this younger core?

Best Regards,

Shane L.

Two questions hope that’s ok!

1) Chauncey has been less than stellar the past two years however he has not been put in the best situations. I think clearly if Dame were staying, this year would have been make or break for Chauncey. Now that we will be in a rebuild again, is that still the case? Does he have to finally show something this year or will he be safe due to the rebuild?

2) Everything depends on the return for Dame, but if you were to guess how long it takes to return to relevancy (competitive playoff team) what would you guess? Best/worst case scenarios?

Appreciate all of your work! You are my favorite sports writer locally or nationally! Keep up the good work.

- Jake N.

Taking these two emails together since they both focus on Chauncey Billups, going into his third season as the Blazers' head coach.

What Shane alluded to about the last two years is something both Billups and Joe Cronin bring up regularly—just how bad of a hand he's been dealt in his first two seasons on the job. We don't need to go over it all again, but between the organizational upheaval of December of 2021, selling off veterans at two straight trade deadlines, Lillard's core surgery two seasons ago and last year's failed "two timelines" approach, it was a far from ideal set of circumstances for Billups to learn the job.

At a certain point, though, this is the NBA and circumstances are never going to be perfect. If the Lillard situation lingers into the season and he's traded in December or January, does Billups get to get a pass for a third year in a row based on these things being out of his control? Results, either in the form of wins or meaningful improvement of the young players, have to come at some point.

I don't know if I'd call this a "make-or-break" year for Billups. Right now, the important people in the organization are adamant behind the scenes that he's their guy. Even as last season went off the rails, I never felt like he lost the locker room, and management still feels strongly about the relationships he's formed within the organization. Scoot Henderson is already giving interviews about how excited he is to learn from him.

But after this season, Billups will be more than halfway through the five-year contract he signed in 2021. There comes a time when the organization will have to decide if he's the long-term guy. It's hard to know what will go into that without knowing, in early August, what the roster is going to look like.

If Lillard is still in Portland, the expectation will be that they compete for the playoffs and whether or not they're able to do that will be how Billups is judged. If he's traded as most people expect, they'll be a lottery team and in that case, free of distractions, Billups will have to provide proof of concept of being able to implement his style for a whole year. I'd bet on him making it through the season. Anything beyond that is impossible to say this far out.

As far as Jake's second question: yes, how soon the Blazers return to relevance will depend on what they get back for Lillard, but more is going to go into it than that. How quickly is Henderson that guy? If his development arc is like Ja Morant's, and Shaedon Sharpe makes a leap in his second year, and other draft picks pan out, they could be decent again in a few years. But that's a lot of if's, on top of the other one we just talked about—is Billups the right coach, and if he's not, will they hire the right coach to replace him?

The worst-case scenario is they're Minnesota post-Kevin Garnett or Orlando post-Dwight Howard and it's a decade-plus before they do anything consequential again. I don't think it will be that long because I think Henderson is going to be really, really good. But how many teams in the position of being talked about as up-and-coming never pan out? What Oklahoma City is doing right now is the best-case timeline, and they have yet to be back in the playoffs since the bubble. A rebuild and youth movement is exciting on paper, but be prepared to wait a while to see results.

Based on team workouts, the eye test, etc - would you say a 19-year-old Scoot looks worse, similar, or better than a 22-year-old Dame post-2012 Summer League?

- Anish B.

Tough to say because we only got to see Henderson play one half of Summer League before he got hurt. Lillard's Summer League in 2012 was the first one I ever covered, and you could tell right away the Blazers had something. But the league was so different 11 years ago, and the expectations around both players were so different. Lillard was a top-10 pick and generally well-regarded by draft analysts, but he wasn't talked about the way Henderson was coming out of that draft.

Lillard was one of the most low-mistake rookies I can remember, especially at his position. The only point guards besides him that come to mind immediately for me as being winning impact players from day one after being drafted that high are Chris Paul, Derrick Rose, Luka Doncic and Ja Morant. Even Steph Curry took some time. De'Aaron Fox was awful his rookie season. So was Russell Westbrook. Even though he has two years of pro experience in the G League, I'm not expecting Henderson to come in as polished as Lillard was as a rookie, because almost nobody does. I'd look for the real star leap to come year two. But I could easily be proven wrong.

Good morning Sean,

I love your coverage of the Blazers by the way. I have read your tweets for a year or so and over time I realized I enjoyed your tweets more than just about anyone else talking about the Blazers. Subscribing to you has been one of the best decisions I've ever made.

Assuming a certain PG is no longer on the team and the Blazers are looking at Scoot, Ant, and Shaedon, as their prime guards, who would you expect likely starts?

Scoot & Ant

Scoot & Shaedon

Ant & Shaedon

Or (my personal favorite): Ant (PG), Scoot (SG), and Shaedon (SF)

I see this as an opportunity for the Blazers to really test what they have in these three. And while they would likely be playing undersized if starting all three, I feel like it's worth testing the waters. After all, it might be nice to have a third year of tanking to grab a player over 6'9" near the top of next year's draft.

Mailbag question #2:

Who will likely get minutes at the backup center position? Will the team go small with Jabari? Is Ibou Badji going to get minutes?

Thank you,

Jonathan E

Thanks for the kind words, Jonathan. Taking these one at a time.

The guard rotation is going to be the most intriguing question Billups will have to figure out. I'd expect Anfernee Simons to start regardless of whether Lillard is still here or not. If he is, it will be the same starting backcourt as last season. If Lillard is gone, Henderson would be my guess, with Simons continuing in an off-ball role like he's played alongside Lillard. Starting Henderson, Simons and Sharpe together is a lot more palatable than the Lillard-CJ McCollum-Norm Powell lineups from a few years ago because Sharpe has the size to fit better alongside two smaller guards, but it's still not perfect. It's going to be interesting to see which way Billups goes, and that won't get sorted until after training camp.

Backup center is also a mystery right now, and that's before factoring in the possibility that Jusuf Nurkic is included in an eventual Lillard trade. Right now, yes, Ibou Badji is the only other true center on the team, and he's never played in an NBA game. It's not a great place to be. They could play Jabari Walker as a small-ball five here and there, but that's a situational thing that can't be the full-time solution.

No matter what happens with Lillard, right now they're two players below the minimum of 14 you have to carry once the season starts, so if things stay status quo on that front, they have to sign two more players. I would think at least one of them will be a big. There aren't many options out there, unless they're able to work something out to bring over Edy Tavares (more on that in a bit).

Hey Sean,

With Jaylen’s Brown’s new green monster bag full of cash that he just inked, there’s a trade kicker - less than 15% of max but exact details are unknown.

One of my favorite Dame trade proposals was the trade to Boston, sending Brown to Houston, returning Jabari Smith Jr. and Tari Eason and a pick or two.

Now with the trade kicker in place, is that something that would likely be prohibitive? Or would Boston ever think of paying it if it meant getting Dame?

Second question:

Nas Little has been swept aside in all discussion since the season ended. How do you see him fitting in with the “Next Chapter” of the Blazers? Do you see the team experimenting with Shape at SF or do they give Nas an opportunity to start the season?

Thanks,

- Jake

The Jaylen Brown question is easy to answer: by rule, because he signed the full Designated Veteran max extension, he cannot be traded for a full calendar year. So that hypothetical deal is completely off the board now, unless the Blazers hang onto Lillard for the full 2023-24 season and they revisit it in a year.

As far as Nassir Little, he'll certainly have an opportunity to earn minutes. My guess today, two months before the start of training camp, is that Matisse Thybulle will be the favorite to start at small forward. Sharpe could see some minutes there, but they see him as more of a shooting guard. These are all questions that will be answered in October, not August.

Two things have to happen for Little to be in the mix there, and they're the same two things that have been true for the past few years. He needs to stay healthy for an extended period of time, and he needs to be more consistent on the defensive end. He's going into the first year of a very reasonable four-year, $28 million extension, and the wing is the Blazers' weakest position besides center, so if he earns minutes, he'll get them.

Do you think the odds are that Edy Tavares is a Blazer next season? Your sourced note about 'mutual interest' was the first I'd heard anything since the July 1st 'offer' report; makes me wonder if the Blazers have Tavares in their plans in a non-dame timeline.

Reading tea leaves, seeing as how a lot of EuroLeague business is already wrapped up, the fact that we haven't heard anything out of Madrid, and the fact that signing Tavares could lever them in a Dame trade negotiation since you can't go over the hard cap even for a moment—appears like it might still happen.

- Sam H.

Like everything else, the pursuit of Tavares will depend on what comes back in the eventual Lillard trade. If they get back some frontcourt depth in whatever the eventual deal is, he suddenly wouldn't be as much of a priority as he would be otherwise. If they don't, they might try to get something done. I broke down the complicated circumstances around Tavares' Real Madrid buyout in a post for paid subscribers last week.

Sean,

As always, love the podcast and newsletter.

Which Blazer(s) are you most excited to cover this season? Scoot seems like an obvious candidate with his background and personality. His sideline interview at summer league was one of the funniest and endearing I've seen in a long time. I think that Shaedon has also started to come out of his shell a bit and it's been great to see him more outspoken and energized on the court, so I hope we can hear more from him and get a better idea of who he is in the post game pressers.

- Keegan S.

I agree that Scoot is the obvious answer here. He seems absolutely delightful, from what little time I've been able to spend around him since he got drafted. He isn't as outlandish or quotable as Anthony Edwards, but they have similar energy, if that makes sense. I'm really looking forward to getting to know him better in the years to come.

I only got to have a few real conversations with Matisse Thybulle after he came over at the deadline, but he's a really thoughtful guy with a wide variety of interests, so I'm looking forward to getting a full year with him.

I also think Ibou Badji is someone fans are going to really like when they get to know him better, especially if he's playing real minutes this year (very possible with their lack of frontcourt depth). Even just talking to him in Vegas last month, his English has improved considerably since the handful of times I talked to him last season, and he seems a lot more comfortable in America now.

Outside of individual players on the team, something else I'm looking forward to this year from a coverage standpoint is the Blazers finally having their own G League team, the Rip City Remix. I plan to be at their games as often as I can, especially since they're playing at the Chiles Center, which is very close to the part of town I live in. I'm already thinking about some cool story ideas I can do involving that.