The news cycle doesn't seem to be slowing down for the Portland Trail Blazers. After firing president and general manager Neil Olshey last week following an investigation into his workplace behavior, the focus has now shifted back to star guard Damian Lillard and his future with the franchise.
Lillard's long said he wants to play for the Trail Blazers over the entirety of his career, but this past offseason rumors swirled that his stance on that topic could be softening given Portland's lack of postseason success over his 10 years there. Yet while Lillard hasn't reached the point of requesting a trade, he made it clear over the summer that he wanted to see changes to improve the roster and boost the team. That didn't happen, and so far the Trail Blazers are 11-13 on the season with the worst defense in the league.
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Due to the Blazers' rough start out of the gate this season, The Athletic reports Lillard has "grown frustrated" with Portland's performance and that "tension appears to be on the rise" with first-time head coach Chauncey Billups and the players. Lillard later vehemently shot that report down on Twitter.
Still, the Blazers don't look any better than they have in previous years, and their defense is worse this season than it was last year under former coach Terry Stotts. One player who could certainly remedy Portland's defensive issues is Philadelphia 76ers All-Star guard Ben Simmons, who hasn't suited up for the Sixers this season, and had hoped to be traded before the season started. Lillard has reportedly expressed interest in playing with Simmons, per The Athletic's Sam Amick and Shams Charania.
There's been rumors over the past few months about the Blazers and Sixers discussing trade packages, primarily one that would send Simmons to Portland in exchange for CJ McCollum, three first-round picks and three pick swaps, but Portland immediately shot down that idea. But with Olshey out, and Portland conducting a new search for a team president, the idea of the Blazers pulling off a trade of that magnitude is unlikely right now, per Charania and Amick.
However, that doesn't mean something can't get done down the line, whether in a trade for Simmons or other players. Portland can still make moves to improve its roster -- and to keep Lillard happy -- by the league's Feb. 10 trade deadline. But if improvements aren't made at the trade deadline, then all eyes will be on Lillard's decision to sign a supermax extension this summer. If he doesn't sign that, it will only open the door further at a possible scenario where Lillard could decide to player elsewhere in the future.