While it has been widely assumed Lillard will accept the two-year extension offer worth more than $100 million that is expected to come his way, sources say the Trail Blazers still needed to have a strong offseason to persuade Damian Lillard to sign on through the 2026-27 campaign (when he’ll be 36). The deadline here isn’t until the start of the regular season, and I’m being told this is not a sure thing just yet.