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.)
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 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.
Spurs executive
Brent Barry, who starred at Oregon State from 1991 to ‘95, was the third finalist 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.
