When Damian Lillard was contemplating a trade request this past offseason, the Portland Trail Blazers had to convince him that staying put was the best thing for his career. They succeeded, but have seemingly done too good a job of it. ESPN's Adrian Wojnarowski is reporting that Lillard now wants a two-year, $107 million contract extension that would pay him $55 million in his age-36 season from the Blazers. Portland recently fired general manager Neil Olshey, but according to Wojnarowski, the sort of top-level GM candidates that Portland would like to consider for the position are not interested in such a contract and would prefer to move on from Lillard sooner rather than later.
Lillard will be eligible for that extension in July, but according to Wojnarowski, he would need the next GM of the team to sell the move to owner Jody Allen. Olshey, who was fighting for his job amid back-to-back disappointing seasons, might have been more eager to make the win-now commitment to Lillard. A new executive with more runway, however, may view things differently. Allen inherited the team after the death of her brother, former Blazers owner Paul Allen, and it is not clear if she plans to keep the team or sell it.
Ironically, Lillard is apparently open to a rebuild… but one he would be involved in. He has reportedly tried to sell the organization on moving some of his veteran teammates for younger pieces with an eye on his long-term future in Portland. Robert Covington and Jusuf Nurkic, both on expiring contracts, are logical trade candidates for the Blazers. Lillard also reportedly tried to get the Blazers to trade teammate C.J. McCollum for Philadelphia 76ers point guard Ben Simmons, but no deal was made.
CBS Sports HQ Newsletter
Your Ultimate Guide to Every Day in Sports
We bring sports news that matters to your inbox, to help you stay informed and get a winning edge.
Thanks for signing up!
Keep an eye on your inbox.
There was an error processing your subscription.
There is no telling how this situation will unfold for the Blazers if they choose not to extend Lillard, whose current contract is guaranteed through the 2023-24 season and has a player option for the 2024-25 campaign, but teams around the league are watching it closely. Three teams told Wojnarowski that they are waiting on Lillard to make a trade request in the hopes that it would lower Portland's asking price. Philadelphia has reportedly made an offer, but the New York Knicks, another team with rumored interest, has not. No other teams are known to have made offers.
The situation might be simpler if Lillard had opened the season on a stronger note. Thus far, he is averaging just 21.5 points per game—his lowest mark since the 2015-16 season—on a career-low 39.7 percent shooting. He is currently out with an abdominal injury and played hurt throughout the Tokyo Olympics over the summer.
Age and injury pose threats to his superstardom in the coming years. He might also simply be adapting to the NBA's new rules and recovering. There's no way of knowing, but signing Lillard for an extra $107 million would be an enormous risk for the Blazers. Mere months ago, they were desperate to bring him back. Now, they are surely wondering if doing so would be worth the price.