Chauncey Billups Won

📍PORTLAND, Ore. — Days before the start of the 2024-25 NBA season, Chauncey Billups, Joe Cronin and several other senior members of the Trail Blazers organization took a redeye from Seattle, where the team had just played a preseason game, to Springfield, Mass., to attend Billups’ Naismith Hall of Fame induction ceremony.

Most of Billups’ acceptance speech was focused on the 17-year playing career he was being honored for. It’s one of the more unique paths to enshrinement that any Hall of Famer has ever taken: a former third overall draft pick who bounced to five different teams in his first five seasons before becoming a champion, Finals MVP and multiple-time All-Star and All-NBA selection by captaining the 2004 Pistons squad that stands as an anomaly in league history, a title team with no superstars.

The speech touched only briefly on Billups’ much less decorated coaching career, which will officially continue in Portland after the Blazers announced a multiyear contract extension on Sunday morning.

“My coaching journey has started off a little like my playing journey,” Billups said onstage in Springfield that day in October. “It’s been a little rough. But I feel the same way as a coach that I did as a player—I will win. Maybe not immediately, but definitely.”

Six months later, ahead of the Blazers' final game of the regular season (a blowout victory over the South Bay Lakers, if you care), Billups and Cronin sat in front of a much smaller crowd, announcing their new deals after a 15-win improvement over last season.

Billups entered the season without a contract beyond this afternoon after the Blazers didn’t pick up his fifth-year option last spring, and he had a lot more at stake than just earning an extension. His coaching record was abysmal (still is—117-211 even after the second-half run), and most coaches with a winning percentage in the .300s in their first job will never sniff another one. Just ask Brett Brown or Stephen Silas how that goes.

If Billups wasn't going to continue his coaching career in Portland—and until mid-January, all indications were that he wasn't—he had to do something to show other teams that he's worth another shot despite his record. The Blazers starting to win at the midway point of the season made the case for him. It just so happens that the team the 23-18 second-half finish sold on him was the one he already worked for.

With his new deal, Billups on Sunday won something that most in his position don't: the opportunity to reap the rewards on the back end of all the losses he's been asked to take over the last four years.

That's the plan, anyway. Neither coach nor GM sounded on Sunday like they had any interest in a fifth straight trip to the lottery a year from now. Cronin called making the playoffs next season a "reasonable expectation," and Billups said they're "moving on" from the rebuilding phase.

If the Blazers get lucky next month in the lottery and land a Cooper Flagg-level talent, Billups won't have to watch someone else inherit him. If Deni Avdija or Shaedon Sharpe become All-Stars in the coming years, he won't have to see a different coach take credit for their development.

The 2023-24 season was a completely wasted year for the organization, with almost no meaningful development and too many injuries to know anything definitive about the collection of lottery picks they're selling to fans as the future. A year later, Cronin is now saying they have "a ton of data" about the roster and Billups is bringing up the unlikely MVP trajectories of Shai Gilgeous-Alexander, Nikola Jokic and Giannis Antetokounmpo to suggest that the Blazers' next superstar could already be on the team.

With that change in messaging is going to come a change in expectations. Billups is now coaching a team that will be judged on results rather than just vaguely-defined "progress." And Cronin, presented this week with a natural opportunity to choose his own coach for the first time after inheriting Billups from Neil Olshey, chose instead to double down on him. Billups wasn't Cronin's hire four years ago, but he's Cronin's hire now, for better or worse.

"You hear everything," Billups said. "I wasn't supposed to last through the first half of the season. Maybe if we don't go on that run, who knows? But I just had so much growing to do last year when they could have picked up that [option]. There were still things they needed to learn about me, that they ended up learning."

Give Billups credit for the unexpected improvement in the second half of the season, when the Blazers stayed alive in the play-in chase until early April. On the day that run began, a Jan. 19 win over the Chicago Bulls, Billups pulled Sharpe from the starting lineup and made no secret that he was being benched for defensive reasons. The change paid off immediately. The pairing of Avdija and Toumani Camara in the starting lineup supercharged the Blazers’ defense, and Sharpe responded to the demotion with improved play that eventually resulted in him winning his starting job back.

Beginning with that game against Chicago, the Blazers won 10 of their next 11 and had two more four-game winning streaks after that. Their defense, which ranked third-worst in the NBA through their first 41 games, has been top-three since the Bulls win.

At first, all the winning felt counterproductive to the organization’s mission, as though Billups was going rogue—why should he care about helping the front office land a prospect like Flagg so someone else could coach him next year? But the development that happened during this stretch, particularly Scoot Henderson’s improvement and the unlocking of Avdija, was something Cronin believed too important to stand in the way of, even as it jeopardized the lottery odds they started the season chasing.

It inadvertently ended up being a situation where everybody acting in their own-self interest was mutually beneficial. And now they both get new deals and added job security out of it.

The alliance between Cronin and Billups has also been mutually beneficial for them as they've navigated huge changes at all levels of the organization, starting in December of 2021 when Olshey was fired after a workplace conduct investigation and Cronin, a Blazers lifer who started as a basketball operations intern in 2006, was thrust into the top job midseason. The ouster of the GM who chose Billups for the job would typically make a young coach look over his shoulder at the new boss looking to bring his own guy in. The Blazers’ upheaval had the opposite effect. Cronin trusted Billups from the outset—the two share Colorado roots and played high-school basketball against each other in the mid-1990s—and Billups' comfort and familiarity with Cronin played a part in Cronin eventually having his interim tag removed the following spring.

The extension Billups signed on Sunday represents a continued belief from Cronin and Blazers ownership in his ability to grow as a coach in the coming years. But it's also a thank-you to Billups for dutifully playing the role of human shield for the organization over the past four seasons. Cronin only speaks publicly a few times a year; Billups talks twice a day on game days and as well as at practices throughout the season. He's the one that's had to answer for all the losses since he took over, even in times when the roster and organizational chaos was out of his control.

And Billups has been a convenient punching bag. Hired by the old GM everyone hated, after a questionable-at-best organizational handling of a 1997 sexual assault allegation that Olshey refused to give Billups an opportunity to address in a way that might have put fans at ease, immediately losing a lot—he checked all the boxes.

The loud boos that have greeted Billups during player introductions for much of the season, which dissipated during the second half of the year once they started winning, were back on Sunday. Maybe they'll continue next season. I suspect that will depend on whether the Blazers make good on the second-half growth Billups and Cronin are touting.

Winning makes a lot of things go away.

"I now understand how long it takes to build a culture," Billups said. "I feel like we've done that. The telltale of that for any coach is the point where a team kind of takes on your personality and how you believe the game should be played, you've gotten there. I believe that the team has done that with me. You never know when that's going to happen. You never know when the team's going to take the leap. You never know if the team will take the leap. But we took some big strides this year."

Billups still hasn't won a lot as a head coach. But on Sunday, he won the chance to be here when the Blazers plan to start winning again.

Now he has to do it.