Once Portland Trail Blazers star Damian Lillard stopped threatening to request a trade, everyone understood his inevitable moment of truth: His future remained bound to the summer of 2022, not 2021. Extensions were always automatic for him, and that's no longer the case.
Lillard wants a two-year, $107 million extension in July, and he and his agent need the next general manager to sell ownership on the idea. As much as anything, this cuts to the core of the Blazers' search process. His desire for an extension into his advanced NBA years has turned into a battle for the franchise's future, an existential threat to reshaping and redirecting the organization in a post-playoff reality.
The prospects of Portland extending Lillard, 31, beyond his $48.8 million in 2024-2025 to pay him $51 million at 35 years old and $55 million at 36 years old threatens to turn an asset of a contract into an albatross.
As former President of Basketball Operations and GM Neil Olshey exits the Blazers, the process to hire his successor will soon be underway. Portland is deciding whether it'll hire a firm to research and recommend candidates, sources said. Bert Kolde, the long-time ownership executive and right-hand man to the late Paul Allen, will direct the search again. He's hired several GMs in his tenure.
The Blazers will be wise to expect every candidate to come armed with two important questions: What are owner Jody Allen's plans to keep or sell the team? And more immediately, would a new GM have autonomy to rebuild the franchise not around but without Lillard?
In the past year, Lillard and his camp have been thwarted on several leverage plays — Jason Kidd as coach, trading CJ McCollum and four first-round picks for Ben Simmons. Most of all, they lost the confidence that the Blazers had a top basketball executive and ownership willing to make Lillard's contract the highest single-season deal in league history at $55.3 million in 2027.