NBA Insiders Expect More Changes After Portland Exec's Dismissal

Jake Fischer@JakeLFischerContributor IDecember 7, 2021

Photo by Steve Dykes/Getty Images) (Photo by Steve Dykes/Getty Images)

Nearly one month after the Portland Trail Blazers announced an independent investigation from law firm O'Melveny and Myers into alleged workplace misconduct from president and general manager Neil Olshey, the franchise fired its lead basketball executive on Friday. 

After speculation that several of Olshey's front office lieutenants could also be dismissed, there have been no other changes to Portland's basketball operations department at this time, league sources confirmed, outside of elevating longtime personnel staffer Joe Cronin to interim general manager. 

The biggest question now looming over the franchise is how this change of leadership will impact the future of Damian Lillard. After a tense summer in which the All-Star guard first voiced his frustration with Portland's direction toward championship contention, Lillard by all accounts has stayed committed to the Blazers and seeing out any early growing pains under first-year head coach Chauncey Billups. 

Yet there still remain internal concerns about Lillard's future in Portland. The last month of investigations and the team's poor record—now 11-14 following Monday's night's loss to the Clippers—combined with mixed feelings about Billups' leadership strategy, all while Lillard has struggled with a serious abdominal injury, has left an unsettled feeling among Blazers personnel despite Lillard's unwavering public commitment to the organization. A lot of work lies ahead. 

How Cronin steers the Blazers forward could dictate Lillard's future in Portland. The stakes couldn't be higher for a franchise that league insiders believe may become eligible for sale following the NBA's next television deal that will start in 2025. 

Over the weekend, Lillard, Billups and Cronin sat down for their first organized meeting, according to one source with knowledge of the situation, to discuss the next steps for a franchise that has greater visions than struggling to make the playoffs. Cronin is considered well-liked and respected among Blazers staffers, yet like many cap-savvy strategists promoted to the big chair before him, he has not had extensive, direct dealings with other teams' top brass. 

Still, Portland's change in leadership has immediately brought into question the status of CJ McCollum, whom Olshey was known around the league to value highly, and perhaps higher than most of his peers. But McCollum's offensive efficiency has petered off across the board to start this season. Now in the first year of a three-year, $100 million contract, it's difficult to ascertain exactly what McCollum could net back on the trade market. 

Swapping McCollum for Ben Simmons has been a popular idea among league figures. Simmons was one of several defensively minded wing players who Lillard has expressed interest in playing with since the 2020 offseason, along with Jaylen Brown and Aaron Gordon, sources said. Olshey did have conversations with the Magic for Gordon, but a deal never came to fruition. Portland instead traded two first-round picks for Robert Covington ahead of the 2020-21 season.

This preseason's trade talks between Portland and Philadelphia never advanced beyond early framework discussions, sources told B/R. Olshey believed the Blazers were constructed well enough to compete in the Western Conference and had little interest in parting ways with McCollum, the No. 10 selection Olshey handpicked during the 2013 draft and seemed to view as equally important to Portland's eight straight postseason appearances as Lillard. 

On the surface, Olshey's firing would seemingly allow the two teams to return to the negotiating table. But ever since Simmons first levied his trade request to Philadelphia officials this summer, it's been difficult to foresee Daryl Morey's front office trading Simmons for McCollum, as the Sixers clearly intend to net an All-Star of equal or greater value in return. Lillard is among a handful of players at the very top of that list, not McCollum. 

There's a greater expectation that any Portland roster shake-up would include starting center Jusuf Nurkic and/or swingman Robert Covington. The Blazers are presently known to be down on both players. Nurkic has not managed to recapture his impact from the Orlando bubble. And under Billups, Covington is playing his lowest minutes total since he first broke into the league with Philadelphia back in 2014-15. 

Moving those players likely wouldn't initiate a rebuild, however low the team's record dips while Lillard recovers from lower abdominal tendinopathy, which has plagued him off and on for several years. (It became clear during the Tokyo Olympics that the injury was again an issue for Lillard, long known as one of the NBA's ironmen. He even contemplated surgery this offseason while seeing a specialist.)

Whenever Lillard returns, the Blazers have a vested interest in surrounding him with playoff-caliber talent. It would appear that any Portland trades would primarily be geared toward shedding $3 million in salary to avoid paying the luxury tax—for a roster on the borderline of the play-in tournament—while also improving the league's 30th-ranked defense. 

Mere months after Portland fired former head coach Terry Stotts for his own purported shortcomings on that end of the floor, Billups ran a dogged, exhausting training camp that had players across the roster speaking of heightened defensive principles, only to see no tangible improvement so far this season. 

Much of the blame does fall on Olshey's shoulders. "That roster just can't be good defensively," observed one assistant general manager. Billups clearly hasn't yet been the missing ingredient either. League personnel far and wide have taken note of the first-year head coach's penchant for blasting players' lack of effort and heart during postgame media sessions. It's a tactic often reserved for veteran coaches like Gregg Popovich. 

Portland has now dropped six of its last seven games. Multiple league sources with knowledge of the situation cited player frustration with Billups' coaching demeanor and the team's offensive system. 

The season is still young. Billups, a former Finals MVP who was recently considered one of the top head coaching candidates in the NBA, has ample runway to make adjustments to his style and schemes. Billups signed a five-year agreement in June. 

The Blazers' next decision atop their basketball operations does seem to bring another inflection point in Portland's power dynamic. 

Billups was known for months in NBA circles as Olshey's front-runner to replace Stotts. And throughout the Blazers' scrutinized coaching search, league personnel suggested the hire's outcome would ultimately point to who swung the biggest hammer atop Portland's operation: Olshey, governor Jody Allen—who was known to support Becky Hammon—or other prominent figures such as the team's vice chair Bert Kolde.  

The GM job could simply be Cronin's to lose. From the onset of the Olshey investigation, Cronin was widely viewed as the logical interim replacement and will be given an opportunity to retain the role long-term. Cronin had recently been promoted to assistant general manager this past offseason, was a candidate for the Detroit Pistons' general manager opening in 2020 and has served as Portland's salary-cap and collective-bargaining-agreement maestro for over a decade. 

The Blazers announced plans to conduct a search for their next permanent general manager, but external outreach has not yet begun, sources said. Multiple figures with knowledge of the situation maintain there are no true candidates, other than Cronin, at this time. 

But the genesis of some of these already-rumored names is not hard to trace in the NBA's latest episode of palace intrigue. Grizzlies executive Tayshaun Prince and Knicks general manager Scott Perry have direct ties to Billups from their contending days with the Detroit Pistons. Shareef Abdur-Rahim, now the president of the G League, is mentioned frequently as a potential candidate among league insiders and is a client of Damian Lillard's agent Aaron Goodwin. 

"To me, you split the difference and go with somebody completely down the middle," said one industry veteran. 

Perhaps that would point to names like Chicago Bulls general manager Marc Eversley, considered a rising front office figure who first worked out of college for nearby Beaverton, Oregon-based Nike. Michael Winger, the respected Clippers general manager, has also been mentioned by several league figures as another potential candidate. Spurs executive Brent Barry, who starred at Oregon State from 1991 to '95, was a candidate for Portland's head coaching post that went to Billups and was considered a favorite of some involved in Portland's ownership dynamic. 

If the rumors prove true—that Allen intends to sell her stake in the Blazers following the NBA's next television agreement—the person entrusted with the franchise the next few seasons will be responsible for more than just optimizing Lillard's window. "If you're putting the team up for sale and make the wrong hire, that would theoretically affect the price," said another high-ranking team official. 

For now, Lillard's health and the cosmetic changes Cronin can juice into Portland's roster will be the first steps in sifting through all these questions. The franchise that owns the NBA's longest active postseason streak suddenly stands on as uncertain a footing as any. 


Jake Fischer covers the NBA for Bleacher Report and is the author of Built to Lose: How the NBA's Tanking Era Changed the League Forever.