For the Portland Trail Blazers, their success lies in the hands of Damian Lillard. The 31-year-old is, arguably, the best player in Blazers history and it's only because of his presence that the team is enjoying an 8-year streak of playoff appearances.
With that fact in mind, it's no surprise that Dame is looking for significant compensation.
According to ESPN's Adrian Wojnarowski, the 6x All-Star is seeking a massive contract extension, one that could net him an NBA record $55 million at 36-years-old.
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.
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.
On the surface, giving Dame that extension sounds like an easy decision for Portland, but there are reports that some executives would be hesitant to make it happen.
Despite Dame's brilliance, the Blazers haven't had much success in the playoffs, only making the Conference Finals once in the past 10 years and, this season, they haven't looked much better. Following Monday night's loss to the Clippers, they moved to 11-14 on the season.
Without a GM to plan their next steps, it's going to take some time before the Trail Blazers figure out what they want to do. But if Dame doesn't get the extension he desires, it could spell the end for his time with the franchise.