The Portland Trail Blazers are staring down the most important offseason of the Damian Lillard Era. They’ve done well in recent years, adding talents like Shaedon Sharpe and Jerami Grant to their roster while hiring a head coach with a fresh outlook in Chauncey Billups that could lead them to a higher plane. Front office hires, like that of assistant general manager Mike Schmitz, have dramatically improved their talent evaluation and ability to build a roster that can dominate.