Report: Damian Lillard looking to sign two-year, $107M extension in 2022

Portland Trail Blazers guard Damian Lillard (0) dribbles upcourt against the Golden State Warriors during the first half of an NBA basketball game in San Francisco, Friday, Nov. 26, 2021 (Jeff Chiu/AP).

Portland Trail Blazers superstar Damian Lillard is looking for a big payday as he reportedly wants to receive a two-year, $107-million contract extension this off-season, according to ESPN's Adrian Wojnarowski.

The extension would reportedly pay Lillard $51.2 million in his age-35 season (2025-26), then $55.3 million as a 36-year-old (2026-27) making him one of the NBA's highest-paid players, according to ESPN's Bobby Marks. Lillard is in the first year of a four-year, $176.3 extension that ends after the 2024-25 season.

Portland is currently searching for a candidate to fill the vacant general manager position after Neil Olshey was fired following an investigation into the team's workplace culture. As Wojnarowski reports, the Trail Blazers' search for its next general manager could be complicated by Lillard’s desire for an ultra-lucrative contract extension in the summer of 2022.

The Trail Blazers’ next general manager won’t just have Lillard’s present and the team’s long-term trajectory to consider when charting a new path forward for an organization that’s clearly reached a crossroads. Whoever succeeds Olshey will be tasked with navigating the fraught nature of a contract extension for the best player in franchise history, too.

In July 2019, after leading the Blazers to a surprise Western Conference Finals appearance, Lillard signed a four-year, max-level contract extension to keep him with the Blazers through 2024-25. League rules make Lillard eligible for a contract extension on the third anniversary of the date his last contract was signed, allowing him to re-up with Portland come late July.

At 31 years old, playing at a substandard level this season and currently sidelined by a nagging abdominal injury, though, Lillard isn’t the shoo-in for that mammoth extension he and his representation hope. Executives across the league have reportedly blanched at the prospect of affording Lillard that extension, dampening their interest in the Blazers’ vacant GM job, according to ESPN.

Among several top-level GM candidates who fit the profile of Portland’s applicant pool, there’s no enthusiasm to grant Lillard his massive extension contract through the 2026-27 season. In fact, several executives told ESPN they would be far more interested in the Blazers job with ownership’s blessing to move Lillard sooner than later.

Lillard is averaging 21.5 points, 4.0 rebounds and 7.8 assists per game this season, shooting 39.7 per cent overall and 30.2 oer cent from three-point range -- numbers well below average based on past production.

He has reportedly expressed interest in being traded to the New York Knicks or Philadelphia 76ers but his preference is to play with Philadelphia.

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