Damian Lillard's loyalty is what has defined his career, and there is no question that he is already a Portland Trail Blazers legend. However, the franchise hasn't yet been able to surround him with a championship-level core, and none of their recent moves really move the needle for the team. Damian Lillard has notably been linked with many trade rumors, creating uncertainty about his future.
However, it looks as though Damian Lillard has addressed the trade talk swirling around him on an Instagram live. In response to a question from a fan that asked him whether he was leaving Portland, Lillard stated that he wasn't leaving at the moment, but seemed to leave the possibility of it happening in the future. A Damian Lillard trade would likely end up as a league-changing move.
There's no question that Damian Lillard wants to win, and that he'd love to do that in Portland if given the chance. If he were to put in a trade request though, plenty of teams would likely offer the Portland Trail Blazers huge trade packages to land him. The opportunity to trade for a superstar of Damian Lillard caliber doesn't come often, and there are certainly teams out there that could benefit from a win-now move.
It remains to be seen whether Damian Lillard does end up requesting a trade this season, or whether he'll ride the year out with the Portland Trail Blazers. There's no question that they still need to make more additions to become a championship-level team, even if they have a solid enough core to be a consistent playoff team. Damian Lillard has shown offensively that he can carry the load, but even he needs some help to make the Finals. Hopefully, the Trail Blazers find the means to make the team better and give Damian Lillard a realistic chance at the title.