More changes could be on the way for the Portland Trail Blazers in due time. Late last week, the Blazers wrapped up their private investigation into their longtime President of Basketball Operation Neil Olshey by parting ways with him after ten seasons.

Now, the Blazers will search for a permanent replacement while Olshey's assistant Joe Cronin steps up to the plate and handles front office moves for the time being. While firing the President of Basketball Ops is a pretty significant change in itself, the Blazers might begin to shake up their roster sometime soon as well.

Despite having championship aspirations heading into the 2021-2022 NBA season, Portland has been quite underwhelming at this point in the year. Twenty-five games into the season, the Blazers possess an 11-14 record and are currently in the midst of a three-game losing streak. 

Shams Charania and Sam Amick of The Athletic reported on Monday morning that the Blazers' superstar guard Damian Lillard is growing fed up with the team at this time. While some might take that as a sign that the six-time All-Star might finally request a trade from the Blazers, Lillard reportedly remains loyal to Portland and would prefer the front office to make a trade for a notable player.

Charania and Amick noted that Philadelphia 76ers' disgruntled guard Ben Simmons is a player Lillard would like to join forces with. However, he isn't the only one. On Tuesday morning, Jake Fischer of Bleacher Report reiterated Lillard's interest in Portland landing Simmons -- but also added two more names that would satisfy the superstar guard.

"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."

The availability of Jaylen Brown and Aaron Gordon is unclear at the moment. While Brown's Boston Celtics had issues early on, which even sparked rumors of possible trade talks between Boston and Philly, the Celtics have looked much better lately as they've won six of their last ten games and maintain a winning record.

As for Gordon, the Nuggets would more than likely have to continue losing at a high rate and reach a point of no return before they move the power forward less than a year after making a move to acquire him. 

If the Blazers are serious about talking shop and looking to make big moves to shake up their roster, they'll undoubtedly hear from the Sixers, who are willing to move on from Ben Simmons for the right price. There's no guarantee Portland can meet Philly's asking price for the young All-Star, but the Sixers have more incentive to move on from Simmons than the Celtics and Nuggets have to move on from their stars.

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