Heading into a fourth straight rebuilding season, Portland Trail Blazers head coach Chauncey Billups remains something of an enigma. The Blazers have wanted to lose, and lose significantly, during the former Hall of Fame point guard’s entire tenure on the job. To his credit, some intriguing young players have blossomed developmentally, including 2023-24 rookies Toumani Camara and Duop Reath, as well as oftl-traveled young small forward Dalano Banton. Shooting guard Shaedon Sharpe, though limited to just 32 games last season, took a leap when he was on the floor, too. Then again, Scoot Henderson — the much-ballyhooed No. 3 pick in the 2023 NBA Draft — had a dismal first season, especially on defense and in controlling the rock. Deandre Ayton, a highly-touted reclamation project after some disappointing playoff runs with the Phoenix Suns compelled the team to cut bait, also plateaued during his first season with the squad last year.

Billups has coached the Blazers to a brutal 81-165 record, but the team hasn’t exactly been trying to win. Even during its final two seasons with All-Star Damian Lillard in tow, the club was poorly constructed and resorted to blatant tanking by the end of the year.

At some point, team president Joe Cronin has to decide whether he wants Billups around long-term. For now, Billups heads into his final contract year on an expiring deal, with no extension apparently imminent. Will he do enough to warrant another deal for next year and beyond? Would he even want to stay with a losing team?

In the latest installment of his podcast Blazer Focused, hosts Aaron Fentress of The Oregonian and Chris Birnbach discussed this very issue.

“One of the biggest things that we’re going to be talking about… is their head coach, who’s got no extension — and that doesn’t count for the salary cap. So what’s going to happen there?” Birnbach wondered. “That’ll be an interesting topic once training camp starts. Not a lot of NBA head coaches go into their last year with no extension and, really, no chance to win. Sometimes they’re like, ‘Well, this is his last year, so he’s got to prove it.’ Well, this roster’s not set up for that, so that’s going to be interesting.”

“One thing in that area — and it doesn’t necessarily mean everything — but he did hire new assistants, he has been involved in planning for the future. They haven’t left him out of talks and discussions and things that are going to be going on in the G League, he’s going to have something to say about that,” Fentress said. “He’s involved with a lot of things they’re doing. That can not mean anything [necessarily], you can be involved with everything, they can just fire everybody… I don’t know how you even go about measuring what he’s doing. He got high praises from Cronin last year and the year before, and [the Blazers] weren’t good. So clearly they believe, at least publically, that he’s done a good job with what they’ve been trying to do. And if what they’re trying to do is lose, well, Chauncey Billups is a master.”

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