According to Chris Haynes of Yahoo Sports, Damian Lillard’s loyalty to the Portland Trail Blazers could be waning:

This report isn’t a definitive trade request. But, Haynes is a top-tier national NBA insider. He is personally connected with some of the league’s best players. Haynes has had many on-the-record conversations with Lillard over the years. So, it seems quite obvious that Lillard or his camp fed that ominous possibility to Haynes. Regardless of the authenticity of his source’s threat, he is one of the few people who would have a real idea of where Lillard’s head is. 

Besides, Lillard did give the impression that he was even the slightest bit bothered by criticism after reports  suggested that Chauncey Billups was destined to be the Blazers’ next head coach:

A bit of background on this situation is needed. Chauncey Billups was accused of rape in 1997. Billups denies the validity of such accusations. However, such a possibility is damning. It is especially damning considering that the Blazers chose Billups over the highly-regarded Becky Hammon. You might recall that Hammon is an assistant on Gregg Popovich’s staff in San Antonio and a would-be first female head coach in league history.

The hire also sends the message that an offender, if guilty, can go on to live a fruitful life while the victim is discarded. This is also damaging from a Blazers’ public relations standpoint. It sends the message that the star player and management want to be led by someone who committed such an act. To be fair to Lillard, his claim to have been too young when the incident occurred to have known about it is valid. But, he also could’ve done some research, too.

Again, these are accusations. No formal judgment has been delivered. So, it would be irresponsible to speculate or judge any further.

What we can fairly and definitively say is that Lillard’s questions about whether the Blazers can field a contender are quite valid. Lillard and the Blazers have made it past the second round of the playoffs just once in his nine seasons with the franchise. His loyalty to the Blazers, their fans, and the Portland community has been unwavering. But, Haynes’ report explicitly says that the criticism Lillard has received from fans has begun to make him question that loyalty. So, maybe it is time for a different look. If that time has come, I think I know a team that might be interested.

Why Should The Sixers Go All Out For Damian Lillard?

It’s Damian freaking Lillard. If he were carrying his team well-above expectations, Lillard would likely be in the MVP conversation every year. For those of you living without the internet, Lillard is a prolific, deadly shooter who can score on all three levels. The years of highlights have proven that Lillard has the power to carry a team for weeks at a time. Joel Embiid has shown a tendency to suffer injuries that hold him out for extended periods of time. Lillard would be the perfect piece to take over if Embiid were to miss time and help the Sixers avoid missing a beat. 

Beyond that, this year’s failure has proven that the Sixers desperately need a lead guard that can create shots for himself. They need a co-star to alleviate the nightly pressure placed upon Embiid to carry the offense. Through its four-year playoff run, Philly has also shown to lack a true ‘closer’. The Sixers glided to the 1-seed this season. But, their attempt at ‘closer by committee’ failed miserably against the Hawks in the second round. The scarring of this season’s blown opportunity is still fresh. Philly should be all-in on prying the star guard away from Portland if he is indeed disgruntled.

Why Would The Blazers Be Interested In A Deal?

This is a better question than the previous one. Anyone would love to have Lillard. Ben Simmons’ incredibly disappointing playoff performance has called his trade value into question. It isn’t as low as Twitter GMs make it out to be. But, it surely isn’t as high as it should be for a 24-year-old three-time All-Star under roster control for four more seasons.

Really, this comes down to what a comparable package would look like. The Blazers should be trying to get younger, not older. They should be thinking about floor-raising or floor-maintaining moves. Hunting for ceiling-raising deals is unrealistic because the reality is that there is no such thing as a ceiling-raising move when you trade Damian Lillard. Bradley Beal certainly isn’t raising your ceiling. Zach LaVine isn’t doing that, either. 

So, there are three potential targets I can think of that would allow the Blazers to get younger, add draft capital, and maintain or raise their floor. One would be forward Brandon Ingram (New Orleans Pelicans). Another that comes to mind is forward Pascal Siakam (Toronto Raptors). Obviously, point forward Ben Simmons (Philadelphia 76ers) would be another option. 

How To Sell The Blazers On Simmons

It certainly shouldn’t be easy to sell Neil Olshey on a deal centered around Ben Simmons. Such is especially the case after Simmons imploded on a national stage. But, there are some fascinating reports leaking about Simmons. ESPN’s Brian Windhorst recently reported that Simmons was doubtful to play for Australia in the upcoming Olympics in order to focus on ‘skill development’. Windhorst later reported that Simmons changing his shooting hand was under consideration as he heads into a career-defining offseason.

If I had to guess, I would say that those are reports out of Philadelphia’s side that are intended to build some idea that Simmons can be “fixed”. So, why wouldn’t Philadelphia be the team to try to fix him? Well, launching a project to build Simmons’ jump shot is not something Philadelphia can afford to do while they have Joel Embiid in his prime. Simmons’ limitations on the offensive end have proven to cap the Sixers out at a seven-game war in the second round of the playoffs.

If a team that is years away from being ready to win a title wants to take a flyer on a star with limitations, they might be willing to buy into that player’s upside. There are a number of pros if they successfully tap into that potential. They look brilliant for figuring it out. More importantly, they expedite their rebuilding timeline because Simmons’ upside forms a top-five player. Additionally, they have additional assets from agreeing to take on what currently looks like a broken piece.

Beyond all of that, Daryl Morey and company might be able to convince a team like the Blazers that a change of scenery in a small market with lower expectations could be all that is needed to fix Simmons. The Blazers might believe they can unlock some of that development. If that’s the case, Simmons instantly becomes the most valuable young player they can get their hands on. 

What A Deal Could Look Like

If Portland is interested in the framework of a potential deal, you don’t not trade for Damian Lillard because of the peripheral pieces the Blazers ask for. They want Tyrese Maxey? Do it and offer free shipping. They ask for Matisse Thybulle? Offer to pay for his flight and preserve him with bubble wrap.

If they ask for both, it’s a tougher pill to swallow. But, you then have to ask yourself if those guys cannot be replaced through other means. Thybulle is an incredible defender. But, is he more than a role player? Maxey showed a ton of poise and promise this season. But, what will he look like when opponents have a scouting report on him? Maybe selling on what looks like a world of potential is the correct move right now.

Beyond that, the Blazers would likely ask for draft compensation. I would think one or two first round picks would do the trick. Perhaps Portland would even agree to some level of protections on those picks, too.

Bottom line: The smell of a possible deal for Damian Lillard is out there. If a trade involving Ben Simmons–after the playoffs he just had–is available, the Sixers should do whatever is needed to bring Lillard to Philly.