The Damian Lillard Dilemma

The Damian Lillard Dilemma

As the NBA barrels toward its offseason, Lillard’s future in Portland looms large.

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You want the Damian Lillard Experience? Cue up Game 2, Trail Blazers-Nuggets. Lillard, arguably the NBA’s premiere sniper, racked up 32 first half points—behind an NBA postseason record eight three-pointers—on his way to a 42-point performance.

Want the Portland Trail Blazers Experience? Despite Lillard’s historic effort the Blazers trailed Denver by 12 at halftime and went on to lose by double digits. Portland was eventually knocked out of the playoffs by the Jamal Murray-less Nuggets in six games.

As the NBA barrels towards its offseason, Lillard’s future in Portland looms large. For years, Lillard has been fiercely loyal to the Blazers. He signed one contract extension. Then he signed another. He is an institution in the city … and in the state … and in the entire Pacific Northwest. He’s not one of the greatest Blazers of all-time—he is, with apologies to Clyde Drexler and Bill Walton, the greatest Blazer of all-time. And at 30, and signed through 2025, he has years to build on that legacy.

But the Blazers are a team at a crossroads. This season’s first round exit was the fifth in Lillard’s nine years in Portland. They have advanced past the second round once in that time, in 2018. They had some injury issues early this season—how Lillard carried the Blazers through that stretch was his MVP case—but entered the playoffs largely healthy. And Denver still knocked them off.

So the question is: What do you do with Damian Lillard?

There’s an argument—a good one—to do nothing. Lillard averaged 29-points per game this season. He shot 39% from three. He is a six-time All-Star that looks like he has (at least) three or four more high level seasons in him. Players like that don’t come around very often. Players like that pop up in Portland less.

There’s an argument—a good one—that the Blazers should put Lillard on the trade block. Take a long look at the way Portland played this season. Is this really a team a tweak or two away from vaulting into championship contention? At a press conference on Monday Blazers GM Neil Olshey suggested the recent coaching change—Portland fired head coach Terry Stotts last weekend—could make a difference. The Blazers were terrible defensively this season. Olshey believes a new coach—as it did in New York and Atlanta—can change that.

“The first round loss and the defensive rating,” Olshey said, “was not a product of the roster.”

Perhaps. But this roster, despite repeated opportunities, has yet to prove it is championship caliber. And bringing back Norman Powell, hoping for the healthy return of Zach Collins and counting on organic growth from Anfernee Simons and Nassir Little probably won’t get it there. Olshey could shake things up—C.J. McCollum, Lillard’s backcourt partner for the last eight seasons, is constantly in trade rumors, and will be again—but can Portland really get a player for McCollum that’s better than McCollum?

Again, maybe. But it’s possible this team has plateaued. Olshey admitted as much on Monday, couching it with his belief that a new coach could change that. But the Western Conference is brutal. Utah is young and only going to get better. Phoenix, provided it can bring Chris Paul back, will too. The Clippers, Nuggets and Mavericks each have superstar laden rosters. And the Lakers still have that LeBron guy.

Lillard’s prime is likely another three or four years—are the Blazers good enough to compete for a championship during it? And if not … why not see what’s out there? There’s evidence that being proactive is more productive than being reactive. In 2013, Boston traded franchise icons Paul Pierce and Kevin Garnett to Brooklyn. What they got back was the draft capital that turned into Jayson Tatum and Jaylen Brown. In 2019, Oklahoma City hit the reset button, shipping out Russell Westbrook and Paul George. The Thunder were among the worst teams in the NBA last season. But they have Shai Gilgeous-Alexander and 18 first round picks through 2027. Not a bad foundation to rebuild on.

There’s also the question of what Lillard wants. For years, Lillard has pushed back on the narrative that he should force his way out of Portland. On Twitter, in 2017: “I’m willing to not win [a championship]. If I can’t build it where I am.” To USA Today, in 2019: “I don’t care what the trend is. I love where I live. I have a great situation.” As Enes Kanter said recently, Lillard “is the most loyal player in the league.”

Lillard’s recent actions, though, makes you wonder if that commitment remains as firm. In the immediate aftermath of the loss to Denver, Lillard posted a quote from the late rapper Nipsey Hussle: How long should I stay dedicated? How long til opportunity meet preparation. And when Portland fired Stotts, Lillard publicly supported Jason Kidd, briefly boxing the Blazers in until Kidd removed his name from consideration.

Lillard privately requesting a deal would make things easier for Portland. But even if he doesn’t, there’s merit to seeing what’s out there. Reports of teams ramping up the pursuit of Lillard are hardly newsworthy. “We check in every year,” says a rival team executive. “You would be an idiot not to.” Lillard’s trade value right now is sky high. But it may not always be. Lillard played through injuries this season. He’s been an NBA ironman for most of his career. If he begins to diminish, the return—Lillard will also make in excess of $50 million per season over the final two years of his contract—will too.

Lillard deserves to win a championship in Portland. But Westbrook deserved one in Oklahoma City. Pierce and Garnett did enough to collect at least one more in Boston. Sometimes, though, individual greatness isn’t enough. Trading Lillard would be excruciatingly painful. The question is—would a few more years of early playoff exits be worse?

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