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.
Lillard’s contract is simply a result of the new contract world we live in. Superstars like Lillard, who have earned their extensions, have to be paid record-breaking contracts in the future in order to stay with the current team.
We are seeing first-hand how this problem has affected players like John Wall and Russell Westbrook, who make themselves a negative asset by making so much money but fail to meet the production worth that large of a contract.
There’s no guarantee that Lillard won’t regress in five years when he’s 36 years old, but the chances are likely that he may not be worth $63 million, which does throw caution into the wind.