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NBA Insiders Expect More Changes After Portland Exec's Dismissal

Dec 7, 2021

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. 

Damian Lillard Responds to Blazers Trade Rumors: 'These Mfs Love Drama Too Much'

Dec 6, 2021
SALT LAKE CITY, UTAH - NOVEMBER 29: Damian Lillard #0 of the Portland Trail Blazers in action during a game against the Utah Jazz at Vivint Smart Home Arena on November 29, 2021 in Salt Lake City, Utah. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement.  (Photo by Alex Goodlett/Getty Images)
SALT LAKE CITY, UTAH - NOVEMBER 29: Damian Lillard #0 of the Portland Trail Blazers in action during a game against the Utah Jazz at Vivint Smart Home Arena on November 29, 2021 in Salt Lake City, Utah. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Alex Goodlett/Getty Images)

Is the clock running out on Dame Time in Portland?

Thus far, Damian Lillard hasn't said as much. Amidst a report from Shams Charania and Sam Amick of The Athletic that Lillard "still wants significant changes to the roster," would like to play with disgruntled Philadelphia 76ers guard Ben Simmons and that tensions are mounting between players and first-year head coach Chauncey Billups, Lillard posted the following on his Twitter account Monday morning:

Regardless of Lillard's tweet, something appears to be brewing in Portland amid the team's 11-13 start. The team already fired former president of basketball operations and general manager Neil Olshey after an investigation into allegations of workplace misconduct, and Billups went in on the team after Saturday's 145-117 loss to the Boston Celtics.

"Competitive fire and pride, that's something you either have or don't have," he told reporters. "That's something you can't turn off and turn on. ... I've never seen a team that needs its bench to inspire our starters. That s--t is crazy to me. It's supposed to be the other way around."

While the Blazers as an overall unit have struggled, so has Lillard. The 31-year-old is averaging 21.5 points, 7.8 assists and four rebounds per game, shooting just 39.7 percent from the field and 30.2 percent from three. 

Lillard has never finished a season shooting less than 41 percent from the field or 34 percent from three, so his shooting woes are surprising, and he hasn't averaged fewer than 25 points per game since the 2014-15 season, his third year in the league. 

A number of factors—an abdominal injury, Billups running less pick-and-roll than his predecessor, Terry Stotts, and the NBA's rule changes contributing to less perimeter fouls and Lillard getting to the line just 4.5 times per game, the lowest mark since his rookie season—are likely contributing to his down season. 

As for Lillard's reported desire to play with Simmons, that seems unlikely. Charania and Amick reported that before Olshey was fired, he had "discussed the framework of a trade for Simmons, moving CJ McCollum, a first-round draft pick and a young player such as Nassir Little or Anfernee Simons to Philadelphia. The 76ers, sources said, at one point asked the Trail Blazers for McCollum and multiple draft picks and multiple draft swaps, which Portland rejected."

Unless the Blazers are willing to move closer to Philly's trade demands, it seems more likely that Lillard would have to join the Sixers if he wanted to play with Simmons than the possibility of being paired with him in Portland materializing. 

And outside of trading Lillard, it's hard to envision the Blazers having the current pieces to make a huge splash on the trade market. Unless Portland turns things around, Lillard's best route to a championship contender still appears to be getting traded to one. 

Blazers Reportedly Received Complaints About Lack of Diversity in Front Office

Dec 6, 2021
General nanager Neil Olshey talks to media after announcing Chauncey Billups as the head coach of the Portland Trail Blazers at the team's practice facility in Tualatin, Ore., Tuesday, June 29, 2021. (AP Photo/Craig Mitchelldyer)
General nanager Neil Olshey talks to media after announcing Chauncey Billups as the head coach of the Portland Trail Blazers at the team's practice facility in Tualatin, Ore., Tuesday, June 29, 2021. (AP Photo/Craig Mitchelldyer)

Among the numerous problems with the Portland Trail Blazers front office, ownership also "received several complaints about a lack of diversity," according to Shams Charania and Sam Amick of The Athletic. 

General manager Neil Olshey was fired last week for violating the team's code of conduct following an investigation into workplace misconduct that started in early November. 

The Trail Blazers hired Asjha Jones in April as their director of basketball strategy and hired Edniesha Curry as an assistant coach in July, but those moves were considered "reactionary."

Olshey, a white man, had been the Trail Blazers' top decision-maker since 2012. Assistant general managers Joe Cronin, Bill Branch and Steve Rosenberry are also all white men. Cronin was elevated to interim GM upon Olshey's dismissal.

According to Charania and Amick, star guard Damian Lillard was among those who noticed the lack of diversity in the front office.

Terry Stotts had been Portland's head coach for nine seasons before he was fired last offseason, spanning Lillard's entire NBA career. The team hired Chauncey Billups ahead of this season while Curry, a former WNBA player, helps bring a new perspective to the sideline as the first female assistant coach in franchise history.  

NBA Trade Rumors: Damian Lillard 'Would Like to Play with' Ben Simmons on Blazers

Dec 6, 2021
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)

Questions remain about Damian Lillard's future with the Portland Trail Blazers, but the team could help him out by making a splash trade for Ben Simmons, per Shams Charania and Sam Amick of The Athletic. 

"Multiple sources have told The Athletic that Lillard would like to play with Philadelphia 76ers three-time All-Star Ben Simmons," The Athletic reported. 

Charania and Amick reported former general manager Neil Olshey "discussed the framework of a trade for Simmons," which included CJ McCollum, a first-round draft pick and a young player. 

Olshey was fired on Friday after violating the team's code of conduct.

The Trail Blazers could continue trade talks to help turn things around after an 11-13 start to the season, including five losses in the last six games. Lillard has missed the last three games due to an abdominal injury.

Portland has reached the playoffs in each of the last eight seasons, but only once in the last five years has the squad made it out of the first round. 

Adding Simmons could get the squad closer to contention by adding a three-time All-Star who was named first-team All-Defense in each of the past two years. The guard would be a better fit in the lineup as he can guard multiple positions without taking shots away from Lillard. 

Simmons, meanwhile, is yet to play this season and remains away from the 76ers due to mental health reasons. He requested a trade in the offseason and could benefit from a fresh start in a new location.

Lillard could also have the chance to play alongside another All-Star for the first time since LaMarcus Aldridge in 2014-15.

Philadelphia has kept a high price tag on Simmons to this point, but the squad could be more willing to make a move after a 12-11 start to the season. Adding a top scorer like McCollum could be worth pulling the trigger after getting zero production from Simmons.    

Blazers Rumors: Damian Lillard Frustrated; Tension Rising Between Billups and Players

Dec 6, 2021
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)

Portland Trail Blazers guard Damian Lillard has reportedly grown frustrated with the direction of the team as tension builds between the locker room and coach Chauncey Billups.

Shams Charania and Sam Amick of The Athletic reported on an increasingly dysfunctional Blazers organization, which fired president of basketball operations Neil Olshey for cause last week after an investigation found workplace misconduct.

Portland is 11-13 after Saturday's 145-117 loss to the Boston Celtics and has many of the same issues that plagued the roster under former coach Terry Stotts. The Blazers are last in the NBA in defensive efficiency, an area Billups was supposed to clean up, and are an abysmal 1-10 on the road.

Lillard is in the midst of arguably the worst season of his career, averaging 21.5 points (his lowest mark in seven seasons), 7.8 assists and 4.0 rebounds per game. He's shooting a career-worst 39.7 percent from the field, including a career-worst 30.2 percent from beyond the arc. The All-Star guard has been out since Nov. 29 with lower abdominal tendinopathy.

The Blazers have undergone massive organizational upheaval over the last year, firing Stotts and Olshey, while CEO Chris McGowan resigned. The team also faced significant backlash over the Billups hiring after rape allegations from his playing career resurfaced.

While the reaction to Billups' hiring led to some questions about Lillard's future in Portland, he's made several clarifying remarks to commit to the franchise. 

“Everybody is saying what they think I’m thinking, and what they think I’m going to do, but like, I’m not leaving Portland, you know?” Lillard told Jason Quick of The Athletic in mid-October.

Lillard said Billups' arrival was a major component in making him want to stay, but the coach's approach appears to be grating on players. Portland has no intention of trading Lillard unless he makes it clear he wants out, so roster shuffling could take place if the Blazers don't turn it around soon. 

NBA Rumors: Latest Buzz Surrounding Damian Lillard Trade, Blazers GM Search

Dec 6, 2021
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)

From title hopes to 10th in the Western Conference. Frustrations are building for the 11-13 Portland Trail Blazers and the firing of general manager Neil Olshey has only added to organizational uncertainty.

There are questions about interim GM Joe Cronin's eventual replacement. Names like Tayshaun Prince are floating around.

On another level, the questions about superstar Damian Lillard's future with the organization have, once again, sparked. And, if he does demand a departure, it's expected that he will head east.

      

Damian Lillard: Future Knick or 76er?

While Lillard has remained relatively steadfast about wanting to win in Portland, that prospect grows dimmer by the day. At an aforementioned 11-13, even the team's playoff hopes are bleaker than ever.

At 31 years old, the All-Star point guard is a frequent discussion point in trade chatter. His team is failing to meet expectations and many think he'd be better off giving his later years to another organization. Now, we have some sense of which potential organizations are front and center.

According to Stephen A. Smith, Dame's preferred destination would be the New York Knicks. But his "camp" wants him to consider another possibility on the East Coast: the Philadelphia 76ers.

Both teams have obvious needs at point guard, especially perimeter shooting, making them good fits. There's still no indication that Portland wants to move him, or that he even wants to leave, but a worsening situation could beget a growing desire for change.

        

Blazers Ignoring Ainge, Considering Prince and Barry for GM

As for who would be in charge of conducting a Lillard trade, if there was to be one? Currently, it's Cronin, but the team is looking elsewhere for a long-term hire.

Journalist Dwight Jaynes reportthat that, to his surprise, former Celtics GM Ainge hasn't been approached for the position.

Instead, Jake Fisher pointed to two more-recent players as potential options: Tayshaun Prince and Brent Barry, who are involved in the Memphis Grizzlies and San Antonio Spurs front offices, respectively.

While Jaynes calls it "ridiculous" that Ainge isn't in the running, the Prince and Barry options are intriguing. Prince has obvious ties to former teammate and current Blazers head coach Chauncey Billups, and Barry is involved in one of the most highly regarded front offices in the league.

Blazers Rumors: Former Celtics GM Danny Ainge Hasn't Been Contacted by Portland

Dec 5, 2021
BOSTON, MASSACHUSETTS - OCTOBER 22: Former Celtics player Danny Ainge waves before the Celtics home opener against the Toronto Raptors at TD Garden on October 22, 2021 in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Maddie Meyer/Getty Images)
BOSTON, MASSACHUSETTS - OCTOBER 22: Former Celtics player Danny Ainge waves before the Celtics home opener against the Toronto Raptors at TD Garden on October 22, 2021 in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Maddie Meyer/Getty Images)

The Portland Trail Blazers have reportedly not made contact with former Boston Celtics general manager Danny Ainge amid the firing of Neil Olshey.

Longtime Portland journalist Dwight Jaynes reported the Blazers are yet to speak with Ainge, who left his post in Boston after the 2020-21 season.

The Blazers fired Olshey on Friday after an investigation found workplace misconduct.

"Out of respect for those who candidly participated in that privileged investigation, we will not release or discuss it," the team said in a statement. "We are confident that these changes will help build a more positive and respectful working environment."

Joe Cronin is serving as the team's interim general manager while a search takes place for a permanent replacement. The Blazers are in a state of organizational upheaval beyond Olshey, with president and CEO Chris McGowan resigning last month and the team firing longtime coach Terry Stotts after the 2020-21 season.

While Stotts' firing was not a shock, there was widespread criticism over the choice of Chauncey Billups as his replacement. Billups was accused of rape in 1997 during his playing career, and the allegations resurfaced after his hiring.

The Blazers have gotten off to a disappointing 11-13 start this season, with several of their issues that plagued them under Stotts continuing under Billups, particularly on the defensive end. 

Ainge took over as the Celtics' president of basketball operations in 2003 and made several successful moves, highlighted by trades for Kevin Garnett and Ray Allen in 2007 that resulted in a 2007-08 championship.

He was also responsible for the team drafting Jayson Tatum (2017) and Jaylen Brown (2016), moves that were made possible by the Celtics cutting bait on the Garnett-Paul Pierce era by dealing the veterans to the Brooklyn Nets in 2013.

Ainge spent two seasons in Portland during his playing career. 

Chauncey Billups Rips Blazers After Loss: 'Crazy' That Bench Has to Inspire Starters

Dec 5, 2021
PORTLAND, OREGON - NOVEMBER 30: Head coach Chauncey Billups of the Portland Trail Blazers reacts during the third quarter against the Detroit Pistons at Moda Center on November 30, 2021 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Steph Chambers/Getty Images)
PORTLAND, OREGON - NOVEMBER 30: Head coach Chauncey Billups of the Portland Trail Blazers reacts during the third quarter against the Detroit Pistons at Moda Center on November 30, 2021 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Steph Chambers/Getty Images)

Portland Trail Blazers head coach Chauncey Billups called out his team after a 145-117 loss to the Boston Celtics on Saturday. 

"I've never seen a team that needs its bench to inspire our starters," Billups told reporters after the game. "That s--t is crazy to me. It's supposed to be the other way around."

Portland was overmatched most of the game, but a rare bright spot came in the second quarter when it outscored Boston 35-26. Larry Nance Jr. (nine points, five rebounds and two steals) and Cody Zeller (10 points, eight rebounds) stood out among the energized bench players.

The starting lineup has taken a hit, as star guard Damian Lillard has missed the past three games with an abdominal injury. Dennis Smith Jr. scored 21 points in his place Sunday while CJ McCollum scored 24, although the latter struggled with his shot and finished 8-of-21 from the field and 3-of-9 from three-point range. 

All five starters were at best minus-14 on the court in the loss to the Celtics.

Portland has lost five of its last six games to fall to 11-13, which puts it 10th in the Western Conference.

Billups is in his first year as the Trail Blazers head coach after replacing Terry Stotts, who was fired after leading the team to eight straight playoff appearances.   

Stephen A. Smith: Damian Lillard Prefers Knicks over 76ers as Trade Destination

Dec 4, 2021
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)
Portland Trail Blazers guard Damian Lillard (0) brings the ball up court in the first half during an NBA basketball game against the Utah Jazz Monday, Nov. 29, 2021, in Salt Lake City. (AP Photo/Rick Bowmer)

If Portland Trail Blazers point guard Damian Lillard looks for a trade out of town, the New York Knicks would be his prime destination, per ESPN's Stephen A. Smith.

On Friday's edition of NBA Countdown, Smith provided a report on Lillard's preferred destination (h/t Kyle Neubeck of the Philly Voice). He also noted that people close to Lillard want him to also consider the Philadelphia 76ers.

The 31-year-old Lillard is in his 10th NBA season. He has played his entire career with the Trail Blazers. The six-time All-Star is averaging 21.5 points and 7.8 assists this year. 

Lillard has repeatedly said that he does not want to leave the Trail Blazers despite plenty of rumors and speculation connecting the point guard elsewhere.

"Everybody is saying what they think I'm thinking and what they think I'm going to do, but like, I'm not leaving Portland, you know?" Lillard said in an interview with Jason Quick of The Athletic in October.

Lillard did admit to Quick that he was internally contemplating leaving Portland after a hard-fought playoff series loss to the Denver Nuggets last season, but he reiterated that he never said he wanted to leave.

"Yeah, I was upset," Lillard said.

"We lost to a team (Denver) I thought we should beat. I wanted us to show we really want to win. But I never said, 'Oh, I'm leaving.' I said, 'If that's what it comes to—if this is not what our real focus is—then maybe I will be forced to say all right, it's not going to work.'

"But I never said I was leaving. And I never said this is not where I want to be. I never said that."

This year's Blazers team is off to a rough start at 11-12. A shorthanded Blazers team just fell to the San Antonio Spurs 114-83. Lillard is also struggling, with his 39.7 percent shooting rate a career-worst mark. The team is also in flux with president of basketball operations Neil Olshey recently being fired for violating the club's code of conduct.

Now might be as good a time as any for Lillard to angle for a trade, as a fresh start for the player and the team could be best for both sides.

Lillard has three years left on a supermax deal (including this season), and he also has a player option for the 2024-25 season. A hypothetical trade involving his contract may not be easy, but Lillard is one of the game's greatest guards at his best, and he could help change the trajectory of any team that acquires his services.

On the flip side, Lillard has made his loyalty to Portland very clear, and its season still has 59 more games on the schedule. The Trail Blazers have the same amount of wins as the fourth-place Dallas Mavericks, so the landscape of the Western Conference is such that the ninth-place Blazers could turn quickly move up the rankings if they can build any momentum.

For now, Lillard is working on returning from lower abdominal tendinopathy, which will force him off the court through at least Dec. 11, per Shams Charania of Stadium and The Athletic. Portland will look to get back to .500 Saturday when it faces the Boston Celtics at home.

What Does Neil Olshey Firing Mean for Damian Lillard and the Portland Trail Blazers?

Dec 4, 2021
PORTLAND, OR - NOVEMBER 23: CJ McCollum #3 and Damian Lillard #0 of the Portland Trail Blazers talk during the game against the Denver Nuggets on November 23, 2021 at the Moda Center Arena in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2021 NBAE (Photo by Sam Forencich/NBAE via Getty Images)
PORTLAND, OR - NOVEMBER 23: CJ McCollum #3 and Damian Lillard #0 of the Portland Trail Blazers talk during the game against the Denver Nuggets on November 23, 2021 at the Moda Center Arena in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2021 NBAE (Photo by Sam Forencich/NBAE via Getty Images)

PORTLAND, Ore. — Following a month-long workplace-conduct investigation, the Portland Trail Blazers fired longtime president of basketball operations Neil Olshey on Friday morning.

Now comes the hard part—figuring out where a franchise in full-on upheaval goes from here.

To understand where the Blazers might go, you have to understand where they've been. The last six months have seen a fourth first-round playoff exit in five years, an Olshey-driven coaching hire criticized for minimalizing the sexual assault allegations against Chauncey Billups, a summer of rumors about superstar point guard Damian Lillard's discontent with the direction of the roster, an assistant coach placed on leave after being indicted in an insurance fraud scheme, the departure of CEO Chris McGowan just last month, and an 11-12 start to the season—not to mention lots of empty seats.

That's before you even get to Olshey's unceremonious exit, which comes the morning after an embarrassing 114-83 loss at home to the 7-13 San Antonio Spurs. It also comes on the heels of the team's announcement on Wednesday that Lillard would be out for at least 10 days as he treats an abdomen issue that has bothered him for several years.

It is against this backdrop that the organization must now figure out how to fix a team that has stagnated and who will be the one to chart their path forward.

Joe Cronin, a front-office lifer who has been with the organization since 2006 and is in charge of managing the team's salary cap, was promoted to interim general manager on Friday. The team said in their statement announcing the move that it still plans to conduct a search for a permanent head of basketball operations.

Whoever that person ultimately is will have a series of tough decisions to make.

PORTLAND, OR - DECEMBER 2: CJ McCollum #3 of the Portland Trail Blazers shoots the ball during the game against the San Antonio Spurs on December 2, 2021 at the Moda Center Arena in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2021 NBAE (Photo by Cameron Browne/NBAE via Getty Images)
PORTLAND, OR - DECEMBER 2: CJ McCollum #3 of the Portland Trail Blazers shoots the ball during the game against the San Antonio Spurs on December 2, 2021 at the Moda Center Arena in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2021 NBAE (Photo by Cameron Browne/NBAE via Getty Images)

Since the start of training camp, Lillard has been pretty definitive about his desire to stay in Portland long-term despite persistent rumors to the contrary. All along, he's pushed for "urgency" in the front office to reshape the roster into a true championship contender. With Olshey now out of the picture and a fresh set of eyes evaluating the roster, previously held ideas about what was possible from a trade standpoint could be upended.

After Thursday's loss in front of a Moda Center crowd that was just over halfway full, Billups, in no uncertain terms, called out the effort of what has become a depressing and listless group to watch on a nightly basis. Their 10-game home winning streak heading into Thursday was offset by a 1-10 road record, and the team is still 29th in the league in defense despite Olshey's offseason insistence that their struggles on that end were due to coaching and not his roster.

Cronin is expected to address reporters in the coming days, which may give fans a sense of where he plans to take the team until a permanent replacement is named. Theoretically, everyone besides Lillard should be on the table in the upcoming efforts to upgrade the roster. 

That includes Jusuf Nurkic, the occasionally impactful but maddeningly inconsistent starting center set to hit free agency in July. That could mean youngsters Nassir Little and Anfernee Simons, who are beginning to break out just as they're up for new deals.

That could also mean CJ McCollum, Olshey's prized draft discovery. A McCollum trade has always been the obvious move to make for a meaningful upgrade, as his pairing with Lillard has repeatedly shown itself to have a hard ceiling. 

Olshey consistently refused to even consider it, preferring to swap out a Maurice Harkless for a Trevor Ariza or a Derrick Jones Jr. for a Larry Nance Jr., rearranging deck chairs on a ship perpetually headed for a seventh seed and a first-round exit.

Maybe the long-speculated-about McCollum-for-Ben Simmons deal becomes a serious possibility now that the Blazers' head decision-maker won't be staking their entire professional reputation on this backcourt.

"We give up size every night," Billups said last month before a home win against the Toronto Raptors. "We are a small group, especially at 1, 2 and 3. They are all pretty much 6'3"."

PORTLAND, OR - OCTOBER 29: Head Coach Chauncey Billups chats with C.J. McCollum #3 and Damian Lillard #0 of the Portland Trail Blazers against the LA Clippers on October 29, 2021 at the Moda Center in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2021 NBAE (Photo by Cameron Browne/NBAE via Getty Images)
PORTLAND, OR - OCTOBER 29: Head Coach Chauncey Billups chats with C.J. McCollum #3 and Damian Lillard #0 of the Portland Trail Blazers against the LA Clippers on October 29, 2021 at the Moda Center in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2021 NBAE (Photo by Cameron Browne/NBAE via Getty Images)

The issue of size with Lillard, McCollum and Norman Powell in the starting lineup is one many around the Blazers have pointed out for a long time, but one that Olshey in June characterized as a false media narrative that "Dame gets frustrated with you guys talking about."

It's too early to seriously evaluate the job Billups has done in his first season as a head coach, good or bad. Olshey put him in a tough spot by placing all the blame for the team's poor defense and disappointing playoff showings at the feet of former coach Terry Stotts rather than seriously overhauling the roster. Billups knows it, too. Maybe the next general manager will give him a lineup that allows him to make the mark he wants to make as a coach.

It's been obvious since the death of longtime governor Paul Allen in 2018 that the Blazers have needed wholesale changes to build a true title contender around Lillard. That was never going to happen with Olshey in charge. Short of Allen's sister, Jody, selling the team, Olshey's exit is the single biggest move that could have ensured at least a chance at giving Lillard a team worthy of what he's built in Portland.

Now, it's up to the as-yet-unsettled new management to deliver on it.

Sean Highkin covers the NBA for Bleacher Report. He is a graduate of the University of Oregon and lives in Portland. His work has been honored by the Pro Basketball Writers’ Association. Follow him on TwitterInstagram and in the B/R App.