When the Portland Trail Blazers extended Damian Lillard earlier this month after a considerable amount of trade speculation this season, the organization and fans rejoiced.
His two-year extension will keep him in Portland through the 2026-27 season and features a $63 million player option in the final year, which concerns The Athletic’s John Hollinger.
Before wrapping up, I should emphasize the “shoot-money-out-the-firehose-on-long-term-deals” approach is far less ironclad once we get into players in their late 20s. That’s still the space where not going too far out on the money makes some sense and is why the Blazers going out so far on Damian Lillard still presents a considerable risk — if he’s washed in 2026-27 at age 36, a $63 million cap hit is still a huge problem.