In an era of the NBA where stars are constantly joining forces to create superteams, Damian Lillard has been an outlier. Despite many fans and analysts begging for him to seek a change of scenery, the All-Star point guard has remained loyal to Rip City. His goal has always been to build a contender with the Portland Trail Blazers, the franchise that drafted him sixth overall back in 2012.

The Blazers have kept a large part of their organization intact for most of Lillard's tenure, but change has been in the air recently. First, the team brought in a new head coach in Chauncey Billups over the summer, and earlier this week Neil Olshey was fired as GM after a month-long investigation into allegations of his toxic, hostile workplace conduct. With Portland clearly in a state of flux, could we be approaching the long-awaited Lillard sweepstakes?

At 31 years old, Lillard only has so many peak years left in the tank. Based on how Portland has started the season, they do not look equipped to make the most of the star guard's talent. They currently sit at tenth-place in the western conference at 11-13 and have one of the league's worst defenses in terms of defensive rating.

Between their record and recent comments, things do not seem to be going smoothly. Following a 145-117 loss to the Boston Celtics on Friday night, Billups hinted at some of the roster being uninspired.

“I've never seen a team that needs its bench to inspire our starters,” he said, per ClutchPoints' Jack Winter, “and that shit is crazy to me. It's supposed to be the other way around.”

It's highly doubtful the Blazers will put Lillard on the block now, but all that could change once the organization hires a new general manager. We cannot forget there was a lot of chatter about Lillard potentially requesting a trade before he left for the Summer Olympics.

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The Houston Rockets invested heavily into Fred VanVleet during the 2023 offseason. Houston gave the point guard a three-year, $128 million deal in a move that was meant to turn the Rockets from a rebuilding team into a championship contending one. The signing did just that, as the Rockets finished the 2024-25 regular season as the two-seed in a stacked Western Conference. VanVleet was the veteran presence and 3-point shooter that the team desperately needed, and he still might have a role with the Rockets going forward. Houston has a team option on his contract for next year, and they very well may pick it up. The Wichita State product reportedly wants to stay in Houston, but the point guard would be set to make over $44 million next season under his current contract. The Rockets and their guard recently pushed back the deadline on Houston's decision with VanVleet, and although reports suggest that they are interested in writing up a new, long-term deal, it isn't necessarily a guarantee that VanVleet will be playing for Houston next year. The Rockets blew him away with an offer he couldn't refuse back in 2023, and another team could so the same when/if he hits the open market this offseason. If VanVleet does become an unrestricted free agent, which teams outside of Houston would make the most sense for him to sign with? 1. Orlando Magic Jalen Suggs and Franz Wagner recently signed big deals with the Orlando Magic, and Paolo Banchero will be getting a mega contract extension here soon. Because of that, the Magic no longer have money to blow like they have had in recent years. That will make a deal for another big ticket free agent hard to pull off, especially considering the team signed Kentavious Caldwell-Pope last year. If Orlando can make the money work, though, then Fred VanVleet would be a great fit with the Magic. The Magic finished dead last in 3-point shooting this season, and VanVleet has made at least 2.5 deep balls per game in every season since 2018-19. VanVleet can hit shots form behind the arc off of the bounce or in catch-and-shoot situations. The Rockets were heavily reliant on his shooting expertise, so the guard would have plenty of familiarity getting up deep shots with high volume if he signed with the Magic. While undersized, VanVleet is a pesky defender, so he'd fit right in with a Magic team that has one of the best defensive units in the league. VanVleet could play alongside Suggs and give opposing teams fits. Ultimately, though, the Magic just need more shooting to get to the next level, and VanVleet is arguably the best shooter who could be available on the open market this offseason. 2. Brooklyn Nets A more realistic option for a VanVleet destination would be the Brooklyn Nets. The Nets are set up to have the most cap space this offseason, and they have a major need at point guard. With D'Angelo Russell and De'Anthony Melton hitting free agency this offseason, the Nets don't have a true point guard under contract for next season. Brooklyn needs to spend big this offseason, and they'd be smart to offer VanVleet a contract big enough that he'd have no choice but to leave Houston. VanVleet averaged 14.1 points per game last season, which was his lowest mark since 2018-19. He is trending the wrong way, but he still has enough left in the tank to give the Nets a few good seasons. 3. Portland Trail Blazers In the same way that the Rockets were looking to take the next step in 2023, the Portland Trail Blazers could use VanVleet's presence to get over the hump. The Trail Blazers have plenty of big man depth, as centers Deandre Ayton, Donovan Clingan, Robert Williams, and Duop Death are all under contract next season. Portland also has a lot of wing depth. Deni Advija started to look like a star late this past season, Toumani Camara is an elite defender, Shaedon Sharpe is a freakish athlete, and Jerami Grant is a proven scorer. The team is thinner in the backcourt, though. Anfernee Simons is a solid scorer, but Scoot Henderson has looked like a fringe draft bust since being drafted third overall. Portland shouldn't give up on Henderson completely, but there wouldn't be any harm in signing another guard. Like the Magic, the Blazers were one of the worst 3-point shooting teams in the NBA. VanVleet would improve that weakness, and in a stacked Western Conference, Portland needs all of the help they can get if they are to compete for a playoff spot.
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If a new GM does come in and decide to blow it all up, the Philadelphia 76ers are a team to watch closely. Since the start of the Ben Simmons saga, Lillard has been at the top of Daryl Morey's wishlist. Things unfolding how they have is why Morey was in no rush to trade the disgruntled All-Star.

During a recent appearance on NBA Countdown, Stephen A Smith mentioned that people within Lillard's camp want him to give the Sixers more consideration when it comes to possible landing spots.

“The only thing that would really tickle him and make him want to entertain leaving Portland, believe it or not, is going to the New York Knicks. There are people in his camp that would like to convince him to give Philadelphia stronger consideration,” Smith said.

As we know, Morey has waited for a trade to surface that puts the Sixers in a better chance to compete for an NBA championship. He was among the last men standing for both James Harden and Kyle Lowry last season. If Lillard were to come available, he will likely do everything in his power to pair him alongside Joel Embiid.

There is no telling how things will unfold. But based on how things have gone in Portland to start the season, the Lillard sweepstakes remain in the realm of possibility.