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The Portland Trail Blazers are running out of opportunities to keep Damian Lillard happy. Following another disappointing playoff run where the Blazers came up short in the first round, many are beginning to wonder whether Lillard is ready for a change of scenery or not at this time.

Although the All-Star has yet to request a trade, there's been some speculation as of late that it's only a matter of time before Portland forces the star guard to ask for a way out as he catches heat for his team's recent coaching hire and the front office struggles to surround him with championship pieces. 

If it does get to the point where Lillard asks for a trade, you can bet the Philadelphia 76ers will come calling. If they do, they'll more than likely offer a significant trade package featuring their three-time All-Star, Ben Simmons.

The Sixers will most likely have one of, if not the best trade package to offer as they have an All-Star they can surround young and high-upside players along with picks for Lillard. But if Portland does decide to swap Lillard with Simmons, one anonymous NBA executive believes the Blazers would catch heat from others for making that move, according to David Aldridge of The Athletic.

"He’s still really good," the executive said of the Philadelphia 76ers star. "But he’s so broken right now, you’re going to get killed if you do that. And, you’re the guy who replaced Dame."

Simmons, who is coming off of a rough showing in the second-round playoff series against the Atlanta Hawks, currently has his trade value at an all-time low. While many teams will still have interest in Simmons if he does indeed become available for a trade, his value as a superstar and face of the franchise type of player is currently in question as his offensive game has clear limitations. 

Lillard has kept Portland relevant ever since he joined the team in 2012. If the Blazers replace him with Simmons, who struggles to make an impact in the playoffs offensively, the Blazers might find themselves in a situation where they'd have to start rebuilding rather than contending. 

The idea of making such a critical mistake could leave Portland extremely hesitant to part ways with Lillard. Also, the idea that other executives around the league would "kill" the Blazers' front office for swapping Simmons and Lillard could be an issue, as well as no front office wants to be the laughingstock of the league. 

Justin Grasso covers the Philadelphia 76ers for Sports Illustrated. You can follow him for live updates on Twitter: @JGrasso_.