Entering a Contract Year, Chauncey Billups Faces His Biggest Challenge Yet
The 2024-25 season is setting up to be a make-or-break moment for the Trail Blazers' head coach.
📍 TUALATIN, Ore. — In his three seasons as the Trail Blazers’ head coach, Chauncey Billups has seen some things. You could fit a whole career’s worth of “seen some things” into those three years.
Billups came to Portland in 2021 (following a controversial coaching search and disastrous introductory press conference) as a first-time head coach expecting to get a real shot at contending with a still-in-his-prime Damian Lillard. What he’s gotten couldn’t be further from that vision. His first 34 months on the job have seen front-office upheaval, injuries, a roster teardown, more injuries, a Lillard trade request, another roster teardown and yet more injuries.
To show for all of that, Billups has a career 81-165 coaching record. He said in no uncertain terms at his end-of-season press conference on Monday that he’s ready for that to change. He called this year’s 21-61 finish the “toughest” season of his career and admitted that he was being "a little unrealistic” when he came into this season thinking he could have the post-Lillard version of the rebuilding Blazers competing for the postseason while also developing Scoot Henderson and Shaedon Sharpe.
“I thought, because we've got some really good pieces on this team, we brought back some real winning type of pieces, I thought I would be able to do both,” Billups said Monday. “And then when we could just never get any continuity with bodies out there, it became very apparent that I probably wasn't going to be able to do both, and that was frustrating. All I care about is winning. That's what made this year so tough for me personally.”
Did I mention he’s entering a contract year?
In his own exit interview, general manager Joe Cronin confirmed that Billups will be back next season while effusively praising him as an “incredible leader” who goes “above and beyond” normal coaching duties to get involved in scouting efforts and organizational staffing interviews.
“His personality is thoroughly felt throughout this building,” Cronin added.
Despite that endorsement, Billups enters the summer with his short-term future secure and his long-term future anything but. Next season, his fourth, is the final guaranteed year on his deal. The Blazers hold a team option for the 2025-26 season that, as of now, has not yet been picked up.
In the NBA—really, across professional sports—all coaches are hired to be fired. Especially ones responsible for the beginning stages of a rebuild, even if that wasn’t what Billups signed up for when he took the job three years ago.
Billups knows all of this. He isn’t running from it.
“In this business, I always feel like you're trying to prove what you can do and what kind of coach you can be,” he said Monday when he was asked directly about his contract status and job security. “I've always felt that way and I feel no different going into next year. I'm looking forward to that opportunity to be able to prove how good I can be. In this league and any league in the professional ranks, you're always coaching for your job. It's a part of the business. But that doesn't scare me. I'm not worried about it. I'll be fine. I'm looking forward to it.”
Cronin and Billups both said on Monday that they’re on the same page about what they want next year to look like. But what they actually said their goals are don’t exactly line up.
Sean Highkin
“For me, personally, I just hope that we can be more gearing towards trying to win first, and then develop along the way,” Billups said. “Which is what I thought I would be able to do this year, and I wasn't.”
“We're heavily invested in a lot of our young guys, so development will continue to be a focus,” Cronin said. “We're not going to win at an extremely high level until some of those guys are ready.”
Ironically, development has actually been one of Billups’ strengths over the past two seasons. Running down the list of young prospects he’s been given by this front-office regime—Henderson, Sharpe, Jabari Walker, Toumani Camara, Kris Murray, Rayan Rupert, even two-way guys like Justin Minaya and Ibou Badji—you’re hard-pressed to find one that isn’t a better NBA player now than they were in October. How much of that is coaching and how much of it is those players’ own talent and hard work? That’s tough to say without being in the room. But Billups and his staff are doing something right on that front.
That track record of development hasn’t led to a lot of wins, though. This year, that was by design. Last year, it wasn’t. But these losses are going on Billups’ resume regardless. If things don’t work out for him in Portland, how many coaches with a career .329 winning percentage get another job? In addition to wanting to win more next year for his own competitive pride, Billups needs to improve that number to either show the Blazers he’s still their guy once the rebuild reaches the next stage, or to convince a different team he’s worth giving another chance.
What Billups has going for him, above all else, is his ability to hold the respect of his players. Some of that comes from his playing career (even before he was officially elected to the Hall of Fame earlier this month, his accomplishments and reputation spoke for itself), but most of it is because he’s a truly great communicator and motivator. The group stayed bought-in and rebounded after their nightmarish January road trip, and again after last month’s 60-point loss in Miami. They never tuned him out or stopped playing hard for him.
The in-game coaching has a ways to go, as Billups will be the first to tell you (he has many times, including Monday). But for a team that knows it’s going to lose a lot, the interpersonal stuff can’t be dismissed out of hand.
“I feel like I've gotten better every single year,” Billups said. “Schematically, me seeing the game and seeing things that need to change quicker. Whether we can execute those adjustments or not, sometimes we can, sometimes we can't. But I take a lot of pride in being able to compete with these teams despite a lot less talent, because of some of the game plans and adjustments that we made that allow us to compete in some of these games that we probably shouldn't. To me, that's growth. So I'm light-years ahead of where I was, but still have a lot to work on as a coach.”
If Cronin wanted to, he could make this talk all go away. He could preemptively pick up Billups’ fifth-year option to remove his lame-duck status for this coming season. He could also sign him to a long-term extension, although that would be wildly premature and unearned for a coach that’s proven as little as Billups has.
The path of least resistance is the one the organization seems to be taking—let Billups finish out his guaranteed deal and absorb some more losses, and then see how everyone is feeling in a year.
Is that fair to Billups? Probably not. But as rare as it is for coaches with his record to get the second or third head coaching job, it’s equally rare for one that’s lost this much to get a fourth year. Billups was traded and cast off enough times in his playing career to know better than anyone that the NBA is a results business. If he has to go into next season on a prove-it year without a long-term commitment, so be it.
“That's a decision that I don't make,” Billups said. “I just try to do the best job that I can, and if they see that there's a value there to do [an extension], that's on them. But I'm committed to doing the best job. Trying to develop, trying to win, trying to teach, trying to compete, trying to mentor. I'm just committed to all of those things. And along the way, those are decisions that they have to make. I'm not expecting nothing. But that's how I move in my life, period. I don't expect anything. I just try to do the best that I can. So that's a question not for me.”
(“With all staff, I'll never get into contract stuff publicly,” Cronin said in response to the same question.)
I don’t think Cronin wants to fire Billups. The two have a relationship that goes back to their days playing basketball against each other in high school in Colorado in the mid-1990s. The mutual respect they have for each other is as strong as any coach-GM duo in the NBA, from what I’ve been able to observe (which has been quite a bit). Cronin wasn’t blowing smoke when he said Monday that Billups is an important voice on key decisions throughout the organization.
But Cronin has to look out for himself, too. Just as his career and professional reputation hinged this past summer on his ability to navigate Lillard’s trade request, how long his time will be in the big job will depend on how quickly the rebuild progresses. Ownership has given him runway for now. That’s not going to last forever.
The Blazers were bad this year and they’re going to be bad again next year. If they’re bad for much longer beyond that, Cronin will have bigger things to worry about than who’s coaching the team. GMs have a few levers to pull when it comes to their own job security. Cronin has already played the trade-your-superstar-and-blow-it-up card.
The next domino is usually the coach, and it’s important to remember that even though Cronin was with the organization at the time, Billups was Neil Olshey’s hire, not his. But if Cronin makes a long-term commitment to Billups, he becomes his coaching choice. Maybe in the next year Billups shows enough growth to earn that commitment, or maybe Cronin decides to bring in someone else to get the most out of the next stage of the rebuild—and buy himself more time to see it through.
99 times out of 100, the latter path is the way this goes.
The same reason the Blazers aren’t in a rush to make a coaching change now—they need to get another high lottery pick and the coach they have has one more year on his contract—is the reason they aren’t in a rush to commit to an extension for Billups, who will likely be playing out next season without a new deal.
How he navigates trying to win for his own sanity, while it’s in his boss’ best interest for him to once again lose a lot, is going to determine his coaching future, in Portland or elsewhere.
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