Chauncey Billups, Trail Blazers Navigating Difficult Dynamic Going Into Crucial Season

Recent staff changes and the uncertainty of Billups' contract status have led to league-wide speculation about the head coach's future.

📸: Alika Jenner, Getty Images

📍 CHICAGO — A lot of smoke has billowed up in league circles in the past two weeks about Chauncey Billups’ future as the Trail Blazers’ head coach and his potential candidacy for other jobs.

The chatter was first reported publicly by Sports Illustrated last Wednesday, but had become inescapable for most of the week—and seemingly came out of left field. After all, general manager Joe Cronin had already confirmed at his April end-of-season media availability that Billups would be back next year for his fourth season.

But since then, there has been considerable reason to question the viability of the partnership from both sides, and that has manifested itself in the situation being a common topic of conversation among team and league personnel at the predraft combine this week in Chicago.

Consider that despite Cronin’s repeated public endorsements of Billups and strong praise for his leadership and influence throughout the organization, the coach is set to go into next season without a long-term contract in place. The Blazers hold a team option for the 2025-26 season; unless they plan to either pick up that option or sign him to an extension, Billups will enter next year as a lame duck, which isn’t a distinction any coach wants.

Consider also that at their respective April 15 exit interviews, Billups said that he hoped the focus going forward would be on competing for the playoffs, while Cronin reiterated that priority one would continue to be development until he could bring more talent in the door. As much as the coach and GM insist that they’re on the same page about their goals, what they’ve said publicly about those goals would suggest otherwise.

Billups’ staff, too, is in the middle of an overhaul with his lead assistant, Scott Brooks, and his brother, Rodney Billups, both not having their contracts renewed earlier this month. The Blazers plan to fill both of those openings this summer, as well as the one created last month when Steve Hetzel left to become the lead assistant to newly hired Brooklyn Nets head coach Jordi Fernandez.

Whether Billups will be the one making the call on those hires or they’ll be foisted on him by upper management, with one of them potentially his successor, is not clear. What all of this does point to, however, is that the smart money is on the Blazers letting Billups finish out his contract, sticking another 50-plus losses on his coaching resume in pursuit of Cooper Flagg, and then doing what every team does at that point: going in a different direction when it’s time to get serious about winning.

With all of this at play, is it any wonder Billups’ future in a job that hasn’t been close to the one he signed up for three years ago has been a topic of conversation throughout the NBA?

According to multiple sources, when Phoenix was preparing to fire head coach Frank Vogel last week, Kevin Durant and other Suns players lobbied owner Mat Ishbia to hire Billups. Other reports this week have indicated that the Suns requested and were denied permission from the Blazers to interview Billups for the job; however, according to a league source, Suns leadership had already zeroed in on former Bucks coach Mike Budenholzer as their hire when the decision was made to let Vogel go.

📸: Alika Jenner, Getty Images

It’s not unheard of for coaches that are currently employed and under contract to come up as targets for other jobs. Tyronn Lue’s name has surfaced in the Lakers’ still-ongoing coaching search, even though nobody in the league thinks they have a serious shot at stealing him away from the Clippers.

In Lue’s case, that’s likely being floated to create leverage for extension talks. With Billups, it’s less clear where the chatter is originating from. Whether or not he was actually approached about the Suns job, or would be interested in interviewing with another team or the Blazers would be open to letting him out of his contract if he wanted to take a different job, comes down to speculation and you’ll get a different answer to each of those questions depending on who you ask.

But there’s a reason teams that might be interested in hiring Billups, and players that look up to him for his Hall of Fame playing career and might be interested in being coached by him, are willing to say out loud that it’s worth kicking the tires on, to the point that that speculation has grown as rampant as it has. Billups’ unsettled contract status is common knowledge around the league, as is the fact that the job he’s been asked to do as the Blazers’ head coach has been very different from the one he and the organization envisioned three years ago, for reasons both in and out of his control.

Billups came to Portland in 2021 expecting to coach a Damian Lillard-led team that had made the playoffs eight straight years under Terry Stotts, who was let go after a first-round loss to a shorthanded Denver team that year. At the time, Billups had just one year of coaching experience as an assistant on Lue’s staff with the Clippers, but president of basketball operations Neil Olshey felt his playing reputation as one of the NBA’s most respected leaders and floor generals would translate quickly to the big job.

Billups’ introduction to Portland was an infamously disastrous Olshey-led press conference that raised more questions than it answered about whether the organization had fully vetted a sexual assault allegation from 1997. Things only got worse from there.

One of Billups’ assistants, Milt Palacio, was implicated in a case involving several former NBA players defrauding the NBPA’s healthcare fund (last week, Glen “Big Baby” Davis was sentenced to 40 months in prison as part of that same case). Then, Olshey, the executive who hand-picked Billups for the job, was fired after an investigation into his workplace conduct, with Cronin being elevated to general manager in December of 2021. Then, Lillard underwent season-ending surgery to address a core muscle issue and Cronin stripped the roster down at the trade deadline, shipping out veterans C.J. McCollum, Norm Powell and Robert Covington and effectively punting on the playoff aspirations they had entering the season.

That was just year one.

📸: Abbie Parr, Getty Images

From there: a promising start to Billups’ second season fizzled out and gave way to a second straight trade-deadline sell-off and late-season tank job. Lillard requested a trade last summer after Cronin didn’t deliver on repeated public promises to make major roster upgrades around him. That saga dragged out all offseason, with Lillard being dealt to Milwaukee less than a week before the start of training camp last fall. The roster that emerged from all of that was filled with intriguing talent but very, very young and firmly in the development stage—and couldn’t stay healthy enough to develop this past season.

Publicly, Billups has been a good soldier through all of this. He’s taken every curveball that’s been thrown at him in stride and embraced the job of teaching and developing young players despite being hired to coach a team expected to win games. Scoot Henderson in particular benefited greatly from Billups’ presence and approach to managing his role and responsibilities amid early rookie-season struggles.

The wins haven’t been there, but Billups is a gifted communicator who has shown an ability to earn and keep the respect and buy-in of his players. If he wanted to make the argument that he’s growing into the job and should get some added security as a show of faith from the organization that his best coaching years are ahead of him, he’d have a credible case.

But he’s also been asked to do a job that isn’t the one he thought he was stepping into, and it’s become clear that his career goals aren’t aligned with the current priorities of the organization.

The close relationship Billups and Cronin have had for three decades, going back to when they played against each other in high school in Colorado, mitigates the usual NBA organizational dynamic where the new GM inevitably looks to replace the coach he didn’t hire. If Cronin does eventually decide to make a change, it won’t be out of a lack of admiration or belief in Billups’ abilities as a coach. Making a coaching change when the rebuild is getting ready to take the next step is just how these things usually go.

If Billups wasn’t who he is in the NBA, just moving on would be simpler. Unlike most first-time head coaches, he isn’t an unknown assistant with no cache. As polarizing as Billups is to fans in Portland, that’s how widely loved and revered he is everywhere else in the league. On both sides, his coaching record has very little to do with it.

The optics of bringing Billups back on a lame-duck contract aren’t great; neither would firing a beloved Hall of Fame player with a lot of allies in all corners of the league when the job he’s in has changed so dramatically underneath his feet—especially if the Blazers don’t have an obvious replacement in mind.

This offseason and the next year will decide a lot of things, not just with Billups’ future but in all corners of the organization. The Blazers are not expected (or planning) to be close to playoff contention next season, and in fact need to get at least one more high lottery pick to push the rebuild forward. Until they find their next foundational star, their success—and their coach’s job security—will be judged on how well Henderson, Shaedon Sharpe and their other young players continue to develop. Much of that comes down to avoiding injuries, and that’s out of anyone’s control. But just like the roster decisions Cronin has to make this summer, he’ll eventually have to make these choices whether he has sufficient data or not. The NBA waits for no one.

📸: Abbie Parr, Getty Images

Last weekend’s coaching staff shakeup, sources say, had been under consideration for months. Hetzel was well-regarded by colleagues and players and likely would have been retained if he hadn’t been offered a promotion to lead assistant in Brooklyn. Letting go of Brooks and Billups’ brother Rodney was part of an effort to revamp things around Billups. It would have been hard to justify making no changes at all after a 21-win season, and if Cronin wasn’t prepared to move on from Billups, switching up his staff was the next logical move.

But as warranted as the staff turnover may have been, it adds another layer of complications to what is already a tough situation. How do you fill three assistant coaching openings that you have to sell to prospective candidates with their new boss going into a lame-duck year?

From all indications, the Blazers aren’t very far in the process of filling those open positions. Part of that is that they’re waiting for the rest of the league’s coaching carousel to shake out and see which assistants are let go as the newly hired head coaches fill out their staffs. But it’s also a tough ask for any assistant coaching candidate who has other options to take a job that may only be there for one year. Billups’ contract status undeniably affects the caliber of names they’ll be able to get.

Rounding out Billups’ staff and getting ready for the draft are the Blazers’ short-term concerns. But at some point between now and next summer, when they have to make a decision on his fifth-year option, Billups and Cronin are going to need to have an honest conversation about whether he’s the right coach for this team at the stage of the rebuild they’re in—and whether the Blazers are the right organization for what he wants for his coaching career.