Damian Lillard Rumors: Execs Feel Contract 'Exactly' Where It Needs to Be for Trade

NBA executives reportedly believe Portland Trail Blazers point guard Damian Lillard is in a good spot contractually to help facilitate a potential blockbuster trade.

Lillard is in the first season of a four-year, $176.3 million contract that features a player option for the fourth season (2024-25).

"The sense I get is that he's kind of exactly where he needs to be contract-wise," Chris Mannix said Wednesday on The Crossover NBA Show podcast. "After this season, there are three more years left on that deal. That's plenty of time for a team that acquires him to figure out how to win with him and not too much time where you start to worry, 'Oh my god, how do we get this guy off our books later in his career?'"

Lillard's future has once again entered the spotlight in recent days.

Shams Charania and Sam Amick of The Athletic reported Monday the six-time All-Star "still wants significant changes to the roster," a call that went unanswered during the offseason, and he's mentioned Philadelphia 76ers point guard Ben Simmons to the front office as a potential target.

If the Blazers don't make the roster upgrades to satisfy the 31-year-old Weber State product, the question shifts to whether he'll submit a trade request before the NBA's Feb. 10 trade deadline, per Charania and Amick.

Then ESPN's Adrian Wojnarowski reported Tuesday that Lillard is seeking to add a two-year, $107 million extension to the end of his contract when he becomes eligible in July, an idea that's been met with hesitation given how it could limit future roster flexibility.

In turn, several executives who could be considered for the team's president of basketball operations vacancy told Woj they'd be "far more interested in the Blazers job with ownership's blessing to move Lillard sooner than later."

Neil Olshey, who served as both president of basketball operations and general manager, was fired by Portland last week following an investigation into his workplace conduct that deemed he violated the team's code of conduct.

Between the upcoming hires to lead the front office and questions about Lillard's future, the Blazers are at a major crossroads that'll likely shape the next decade of the franchise.

They must decide whether to keep committing to Lillard's vision for the future, which could include giving up numerous assets for a marquee name like Simmons, or instead move their own longtime face of the franchise to begin charting a new path.

Lillard is off to a sluggish start to the 2021-22 season—his 21.5 points per game are on pace for his lowest scoring figure since 2014-15—but he'd still be an attractive trade candidate given his strong track record.

More clarity on the Blazers' future will likely come before February's trade deadline but probably no later than the 2022 offseason.