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Report: Damian Lillard seeking massive extension from Blazers this summer

All-Star PG is under contract through 2024-25, but is looking to tack on a few more years at a salary north of $50 million.

Damian Lillard # 0 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 have some of the most difficult decisions to make throughout the rest of this season and entering the Summer of 2022. Most notably is the future of franchise PG Damian Lillard. The All-Star guard is under contract through the 2024-25 season and is seeking another extension this offseason, per ESPN’s Adrian Wojnarowski.

The reported extension would make Dame the highest paid player in the NBA at two years for $107 million, north of $50 million per season in 2025-26 and 2026-27, when Lillard is set to be 35 and 36 years old. Such a deal getting done as early as 2022 would make Lillard’s contract almost immovable. This puts the franchise is a tough position. Do you ship out the cornerstone guard now and begin a rebuild or do you keep him around for the rest of his career to appease to the fans and city?

The most logical thing for the Blazers to do is trade Lillard. It’s not going to be popular and it’s likely going to hurt the franchise in the short-term, but is the best way to go in the long-term. Lillard is great, but clearly on the decline this season. He’s 31, injured at the moment, and in the midst of his worst NBA season since 2014-15. Lillard is averaging 21.5 points and 7.8 assists on shooting splits that are way down across the board.

So how do you keep and then extend a great player who is on the decline? It’s just not a smart move in today’s NBA.

The other side of the argument is trading Lillard would be a poison pill to the franchise. The team would be admitting defeat this season and realizing that the team isn’t going to be a title contender with this core. Most of the casual and diehard fans won’t be happy with Lillard’s departure. Ticket sales are already down in Portland. So the Blazers may not have a choice but to keep Lillard and hope he rebounds and finishes his career strong.

This would mean dealing CJ McCollum is the route the front office must take. McCollum’s contract is easier to deal with only two seasons left after this one. He’s younger at 30 years old and has been one of the more consistent shooting guards in the NBA over the past seven seasons. Portland can look to deal McCollum for a dominant big or wing player to pair with Lillard while moving Norman Powell and Anfernee Simons into more prominent roles in the back court.