Why Damian Lillard’s best shot at a title might still be in Portland. If he has patience

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PORTLAND, Ore. — If Damian Lillard is as loyal as he says he is, and if he’s as smart as he thinks he is, then the solution to his “problem” in Portland is simple. That’s an idea voiced by reader Kacy H. in a comment on a story I wrote about Trail Blazers general manager Joe Cronin drafting three youngsters last week instead of acquiescing to Lillard’s public request to use the picks in trades for documented veterans.

The key passage in Kacy’s commentary: “Dame is my favorite Blazer of all time and I hope he stays, but to sacrifice the future of the franchise just to make Dame happy would have been a huge mistake. Stick with us, lady. Give it a few years. Cronin becomes shrewd and calculating. This team may still be your best bet for a championship. You might just not be the best player on the team when that happens.”

Kacy’s concept is so simple, so smart and so concise. And that really puts Lillard’s entire title talk under the spotlight. Is Lillard really about winning a championship? Or is he all about winning a title as a headliner?

I have to admit that the most romantic story, the one most fitting and poignant, would be Lillard winning a title in Portland after mentoring and instilling in Scoot Henderson and Shaedon Sharpe the same traits that define his own career: that being a great leader, being a selfless teammate and being an involved citizen. It is also the most realistic scenario.

Portland is unable to make the moves that would vault them into championship contention next season when Lillard turns 33. Or likely the next. And by the time Henderson and Sharpe are ready to lead Portland into battle, Lillard may come off the bench and he may make the big shots for child prodigy. But would the goosebumps be less, or the emotion less, if Lillard’s beard was speckled with gray hair and his eyes had a hint of crow’s feet? Of course not. Him lifting that Larry O’Brien trophy would be among the sentimental moments in sports.

We are all here today considering Kacy’s concept because Cronin has not lived up to his word. He said his intent is to build a winner around Lillard. But almost all of his moves since taking over have been about cutting long-term wages and scooping up promising young talent. It’s such a blatant case of doing the opposite of what you say that Lillard and his agent felt the need to meet with Cronin on Monday in Portland to discuss the direction of the franchise.

People like Lillard and his agent don’t call such a meeting when they’re happy or encouraged by what they see. But … maybe Lillard should. If Lillard really is as smart as Cronin says he is when it comes to the salary cap and the bargaining chip, and if Lillard is really as keen on what kind of talent it takes to win at this level, and if Lillard is really loyal to Portland after the hundreds of millions of dollars the Allens have pumped into his bank account, he would see what Kacy and more and more are beginning to understand: What Cronin is building could be big time. It will just take time to grow up.

There is a long list of needs and gaps in the current roster. The Blazers still have a gazillion guards. They still only have one player — center Jusuf Nurkić — taller than 6-foot-9. And there’s still no clear commitment to address what has been one of the NBA’s worst defenses over the past four seasons. For the Blazers to be the contenders Lillard so badly wants, they must address all of these areas this summer with limited resources to make it happen. There is a spartan free agent budget. A modest trade exception. And a roster that doesn’t exactly entice other teams to part with their impactful starting wing.

So build a winner around Lillard for the next few years? It’s not an easy task, but it’s a corner Cronin and chairman Jody Allen have backed themselves into. Last week’s draft was the first time under Cronin that the franchise was put ahead of the franchise player. It was a bold decision by Cronin to stick to his guns about Scoot Henderson’s value, but it came at the expense of his word, not only to Lillard, but to the fans. How much does anyone believe Cronin is committed to building around Lillard when — with the exception of acquiring Jerami Grant — in every acquisition period (draft, free agency, trade deadline) Cronin makes moves that deviate dramatically from Lillard’s timeline?

Cronin’s vacillation between two timelines is why I was concerned when Jody Allen promoted Cronin to replace Neil Olshey without interviewing a single candidate. Not one. After Olshey was fired, I was told that Michael Winger, then a Clippers executive widely regarded as one of the brightest young minds in basketball, would have interest in the Blazers’ opening. The Blazers didn’t bring him in to hear his vision, to get a sense of how he would change the Blazers. Interestingly, Winger was hired in May to lead the Washington Wizards, a team often compared to Portland as it continued to extend an aging franchise player in Bradley Beal while the team battled through mediocrity. Less than a month after Winger was hired, he traded Beal, shipped out fellow star Kristaps Porziņģis and embarked on a Wizards rebuild.

It is interesting to see how the two managers, both whose skills are rooted in salary cap expertise, navigate their own landscape. I’d like to think Cronin sees in Portland what Winger saw in Washington — the absence of logic in pushing up against the luxury tax line with a roster that treads water. Cronin says he’s taking a different tack, even if his actions don’t back up his words. However, Cronin continues to fan his own flames by saying he and the organization “owe” it to Lillard. They don’t. They owe it to the fans and the person who owns the team to do what is best for the franchise. No player is bigger than the organization.

You owe Lillard?

The hundreds of millions in salary are not enough? The free pass on his lack of defense is not enough? Overlook his playoff struggles, which included a 5-for-31 3-point shooting performance while outplayed by Mike Conley in 2015, his choke of Jrue Holiday during a sweep in 2018, 3-for-17 performance in Game 7 in Denver, who was forgotten in the midst of CJ McCollum’s heroics … all that isn’t enough?

He is worshiped here – with good reason. He has been involved in the community more than any player I can remember. His teammates love him. He works hard. He has been fantastic, special, both on and off the pitch. His number will be retired and there will be a statue.

But this continued anxiety about whether the organization is doing enough for him … are they surrounding him with good enough players … is he happy? It has become exhausting. On the fan base. The organization. No one forced Lillard to sign his extension to stay here. And if we expect Cronin to back his word about building the best roster, shouldn’t we expect Lillard to back his word about loyalty?

For the first time since the team reached the Western Conference finals in 2019, the organization has a pep in its step again. That pep is no longer just about Lillard, but it can certainly include him. By all accounts, everyone wants it to include him. Now the decision is Lillard’s. Chase a title elsewhere, or see if there’s one in the offing here in Portland.

Jump aboard, lady. That’s the Kacy concept: What gets built here in Portland might be your best shot at a championship. You might just not be the best player on the team when it happens.

(Photo of Damian Lillard and Shaedon Sharpe: Sam Forencich/NBAE via Getty Images)