The Portland Trail Blazers' roster confusingly has two entirely different timelines. That was a problem the past few seasons, but it became exacerbated this summer after acquiring aging star guards Jrue Holiday and Damian Lillard. On the veteran side of things, Portland now has Lillard (35), Holiday (35), Jerami Grant (31), Matisse Thybulle (28), and Robert Williams III (27).
Blazers general manager Joe Cronin has made it clear that it's "winning time" in Portland after their 15-win improvement from last season and offseason moves. The Blazers are looking to win as soon as next season with ambitions of ending a four-year playoff drought, which seems even longer for a franchise that has become accustomed to regular-season success.