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What should the Trail Blazers do with Damian Lillard?

Portland’s star point guard wants a massive extension on top of his maximum contract. We look at whether or not the franchise should trade him or keep him.

Los Angeles Clippers v Portland Trail Blazers
Damian Lillard of the Portland Trail Blazers participates in shoot around before the game against the Los Angeles Clippers at Moda Center on December 06, 2021 in Portland, Oregon.
Photo by Soobum Im/Getty Images

The Portland Trail Blazers may be reaching a breaking point with star Damian Lillard, who is seeking a massive extension this summer, according to Adrian Wojnarowski. Lillard still has two years plus a player option left on his contract at the conclusion of this season, and wants a salary north of $50 million according to the report. Lillard’s current contract will pay him $42 million and $45 million over the next two seasons, with a player option for $48 million to follow.

Let’s get one thing out of the way; the Blazers have won a lot of games with Lillard. They’ve made the playoffs every season since his second year in the league, reaching the Western Conference Finals in 2018-19. They’ve also had five first-round exits, which can get tiresome no matter what your paycheck looks like.

It seemed like Lillard was fine with the franchise’s approach until this offseason, where he pushed for the front office to make moves. The organization stayed largely pat due to the inflexibility of Lillard’s and CJ McCollum’s contracts, which surely angered the point guard. There was also the hiring of head coach Chauncey Billups, which came with a lot of public criticism. Primary decision maker Neil Olshey was recently fired for violating the team’s code of conduct, throwing the entire franchise for a loop.

Lillard has been a productive player, but it’s reasonable to ask how much he can do as he enters the back end of his prime at 31. The point guard is averaging 21.5 points and 7.8 assists per game but Portland needs more from him at his current cap number. Lillard is +7500 to win MVP, according to DraftKings Sportsbook, good for 18th overall. He’s +4000 to lead the league in scoring and +4500 to have the most assists, good for 11th and 12th overall, respectively. You can start to see where the salary doesn’t match up with the production.

Portland doesn’t have many options here in terms of a trade. Lillard’s salary is near the top of the league, meaning a contending team would have to be willing to deem the guard a clear upgrade over a current productive player. The Philadelphia 76ers and Brooklyn Nets are logical options but the Blazers likely don’t want to deal with Ben Simmons or Kyrie Irving. The Golden State Warriors have some intriguing young players and enough salary filler to make a deal work, which would also give Lillard a chance to play in his hometown. Expect a lot of teams to be interested if the Blazers do decide to make Lillard available.

This would also mean Portland’s other pieces would likely get dealt. McCollum, Jusuf Nurkic, Robert Covington and Norman Powell would all be on the block if Lillard was dealt and the Blazers would have to truly rebuild everything. Billups didn’t sign up for this, so his future would also be in question in this scenario.

Lillard’s extension demand is simply asking for the franchise to repay him for his loyalty. He could’ve easily bolted this summer but chose to stick around and give his new head coach a chance. Portland’s best bet to keep making the playoffs is extending Lillard, the only entity Blazers fans can point to with pride in recent years. It’s going to be very tough to ship him out.