Damian Lillard reportedly wants the biggest contract in NBA history and the Trail Blazers have a decision to make

Damian Lillard might be on the move soon.

The Portland Trail Blazers have a ton of big decisions to make, all of a sudden.

First, they need to find a new GM after dismissing longtime executive Neil Olshey behind the mistreatment of employees within the organization. But that’s just the first decision they’ll need to make.

The most important one will determine the future of their franchise going forward. And that is whether they’ll offer Damian Lillard the massive two-year, $107 million extension he reportedly wants, according to ESPN’s Adrian Wojnarowski.

Calling that a massive deal might be an understatement.

The Blazers’ All-Star point guard’s current deal takes him through the 2024-25 season, but he wants to tack two more years onto it. The extension he wants would reportedly have him paid $55 million at 36-years-old, which would be the biggest single-season payout in NBA history.

It’s not unreasonable for Lillard to ask for that extension if he indeed wants it. He is the best Portland Trail Blazer ever. He’s held them down in ways no one else has before.

But it’s also true that he’ll be 36-years-old and, more than likely, on the decline. And that’s a massive chunk of cap space to dedicate to one player.

That’s something that, apparently, NBA GM’s the Blazers are looking at are reluctant to do, according to Wojnarowski.

“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.”

That’s a tough situation to be in. Do you part ways from the face of your franchise or do you keep going? Neither is an easy path. And, honestly, the fact that this story is out tells us which way the Blazers are leaning — and it’s not in Lillard’s direction.

But, regardless, we’ll know where they stand sooner rather than later.