The Ins and Outs of Damian Lillard’s Big Contract Extension

The Portland Trail Blazers and franchise superstar Damian Lillard agreed to a two-year, $122 million extension that will keep Lillard on the NBA salary rolls through the end of the 2026-27 season. The deal will top out at $60+ million in his final year, bringing his average salary for the next five seasons over the $50 million mark.

Over the weekend, Lillard and the Blazers held a press conference at the NBA’s annual Summer League from Las Vegas, Nevada. During the interviews, Lillard talked about wanting to win a title, improving the team, and being fine with the pace and road upon which the Blazers were proceeding. Blazers General Manager Joe Cronin affirmed the organization’s commitment to making Lillard a “lifetime Trail Blazer”, stating this contract was one of the steps along that journey.

Even so, the extension provoked a few questions in the Blazer’s Edge Mailbag, including this one.

Dear Dave,

They finally did it. Dame is now one of the best paid players in history and everyone seems happy, but I have mixed feelings I guess. He’s Dame so it’s good. The only other players in my lifetime I’ve seen as good as him were Clyde and Walton. I think we all know that. But he’ll be 37 when this contract expires and I don’t know if this is best for the team. I want to hear what you’ll say.

Larry in Beaverton

I agree with you that multiple angles shoot through this story.

In the abstract, Damian Lillard is worth every penny he can earn. You’re correct in your assessment about his talent. We can’t put him in the same category as MVP-level superstars who have won titles in this generation: LeBron James, Kevin Durant, Steph Curry, Giannis Antetokounmpo. He belongs in the next tier down with Bradley Beal, Luka Doncic, et al. Since the former list is, like, four players long while NBA franchises number 30, the Blazers are perfectly justified in valuing Lillard highly and moving to reward him accordingly.

Via this move, the Blazers signal that they are serious about maintaining a high level of play, that free agents can trust the lineup they’ll join in Portland, and that any future superstars looking their way can be assured the team will be loyal and compensate them appropriately. This was about the brand, not just the numbers.

Keeping Lillard will also help them on the floor. The only way he would be replaceable is if the Blazers wanted to rebuild from scratch. Even then, the team would not receive direct compensation for his talent. They’d receive future assets to grow them into a new era: multiple draft picks and young players who would leave the team less competitive now, but jump start them on the way to revival.

They didn’t go that route. As soon as Portland traded for Jerami Grant and re-signed their own free agents for big bucks, extending Lillard was all but predetermined. The only question was timing, which they did at the biggest NBA gala of the summer.

Whether the move is prudent for the future, no one can say. You’re correct that shelling out $50 million for a guard in his mid-thirties isn’t in the Big Book of Good Ideas. The Blazers are willing to absorb that risk. If they have to pay during the extension years for the possibilities opened today, they wouldn’t be the first or only team to do so. Honestly, nobody can guarantee the team would be in better shape in 2026 if they started over right now. We just know they’d be four years into the experiment instead of putting it off.

For Portland, the chances of shooting for contention over the next 3-4 seasons looked brighter than the chances of lightning striking with an earlier rebuild. That was enough to tip the scales for them to offer this extension.

For Lillard, of course, this is a no-brainer. He gains everything, loses nothing. It’s likely he would have received compensation from any team he joined as a quid pro quo of a trade. Someone was going to pay him! That the Blazers did so not only affirms him, it puts the money in his pocket as early and seamlessly as possible. It insures him against future injury and any twist of fate that might derail his presence or production.

If somebody says, “You can do X, or you can do X and we’ll guarantee you $122 million more for it,” there’s only one answer to that question.

The only part of the process that’s at all specious is the, “Now he’s here forever,” story. This signing keeps alive the possibility that Lillard can and will remain with the Blazers for life. It does not ensure it, any more than Durant’s current four-year deal with the Brooklyn Nets ensures that he will remain there.

Obviously both sides are going to play up the good feelings, which no doubt remain real at this point. In reality, no future possibilities were closed, or changed, when this extension was signed, other than the possibility that Lillard would be unemployed between 2025-2027. That was highly unlikely.

Even after the extension, Lillard retains his superstar leverage over the team and the league, undiminished. If anything, it’s confirmed as he’s now, as you’ve pointed out, one of the best-compensated players in the history of the game.

The Blazers did not gain more Lillard by signing this extension as much as they avoided alienating him by refusing to sign it. They still have to work to keep him, but at least they and their fans can rest easy in the knowledge that they didn’t lose him.

Anything can happen in the future. from a lifetime of Lillard in Portland to a trade demand next summer to injuries making this extension look like a giant facepalm in the years to come. For now, both parties controlled what they could control and, at this juncture, in the Summer of 2022, both are saying they’re happy. That’s as much as can be accomplished for now. Worrying about the future is understandable, but now that the ink is dry on the deal, the only real response is to click down to low beams and focus on the twists and turns of the season ahead.

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