The Portland Trail Blazers and the Damian Lillard Conundrum

Liam McKeone

The Portland Trail Blazers’ season ended on Monday night in disappointing fashion, blowing yet another second-half lead to the Golden State Warriors that resulted in a sweep and a playoff exit.

On Tuesday, it was announced the team was planning to offer franchise cornerstone Damian Lillard a max extension this offseason, worth $191 million. It’s an important move for both the team and Lillard. He’s made it abundantly clear he has no desire to leave, and his one goal is to bring a championship to Portland and only Portland. But it puts Portland in a tough spot, and its situation encapsulates the struggles that most teams in the tier of “good, but not good enough” deal with.

Lillard absolutely deserves this extension. He’s a huge figure in the Portland area and truly rides and dies with their fans. His first-round performance against Oklahoma City was the stuff of legends. But the question isn’t about Lillard’s accolades as much as it is about Portland and what paying Lillard a supermax extension does for their franchise. Depending on the structural details, it’s likely Lillard’s salary would jump about $10 million from the extension when it kicks in. Worthwhile for a player of Dame Dolla’s caliber, but Portland is already tight against the cap as is thanks to giving big contracts to players like Evan Turner and Meyers Leonard (who showed up in Game 4, but still doesn’t deserve the amount of money he’s being paid).

It’s a microcosm of the dilemma most NBA teams treading water in the middle class of the NBA face. Lillard means everything to the franchise, but there’s also a pretty clear-cut blueprint to stopping him that has been used to shut him down during every playoff series loss. If you aggressively trap Lillard on pick and rolls, he can’t pull up and has to pass it to his teammates. It’s a similar method to stopping Steph Curry, except Lillard doesn’t have a playmaking forward like Draymond Green to roll to the bucket and make the right pass on every trap play. Unfortunately, paying Lillard more money, no matter how much he deserves it, does nothing to fix that issue.

It’s not as simple as saying the Blazers should use the money they would’ve given to Lillard to sign better players. If it were that easy, everyone would do it. But giving Lillard a supermax while he still has two years left on his current contract limits the Blazers’ opportunities to take a chance on someone who may become available, either on the trade market or in free agency. Is it worth giving up that opportunity to give Lillard the money he’s earned? Maybe. Locking down homegrown stars is the lifeblood of small-market teams, and Lillard is as close to a God-like figure in Portland as any player in the league is in their respective city. He’s enough of a superstar to drive the team to win after win, but needs help to get over the final hump.

Such is the internal struggle every franchise faces that has found themselves in Portland’s situation. Trading off financial flexibility to reward those who deserve it has been a decision throughout all sports. Portland has chosen its path. All it can do is hope it was the right one.