Damian Lillard has long been loyal to the city of Portland and the Trail Blazers franchise. He is definitely a Trail Blazers legend and has led the team to a Western Conference Finals appearance in the 2019 playoffs.
Despite his continued commitment, to the Trail Blazers, it seems as though there is a chance Damian Lillard could move on in the future. Eric Pincus of Bleacher Report has revealed that the New York Knicks could potentially be Lillard's "next destination" if extension talks with the Trail Blazers end up going "south".
Most teams expect the Trail Blazers to extend Lillard for another couple of seasons at roughly $100 million, but if that goes south, the New York Knicks may be his next destination over the Sixers.
There is no doubt that the New York Knicks have not had a star of Damian Lillard's caliber for a long time. Julius Randle made the All-Star team last season but has definitely not looked the same this year. It would definitely be entertaining for Knicks fans if Damian Lillard made his way over to New York. This isn't the first time Damian Lillard has been linked with the Knicks, and Stephen A. Smith notably claimed that Lillard would like to play for the Knicks if he were to request a trade.
However, it does seem as though the Trail Blazers will try to extend their star. As Pincus mentions, "most teams expect the Trail Blazers to extend Lillard" for a few more seasons at "$100 million". It makes sense for them to extend a franchise legend and try to win a championship with him.
It would be amazing for Damian Lillard to win a championship with the Trail Blazers, but that is unlikely to happen this season. They are currently the 10th seed in the Western Conference, and Damian Lillard hasn't returned for the franchise yet. Hopefully, we see the team become competitive sooner rather than later, but it's clear that this season might be a period of retooling for the franchise.