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With the superstar's clock ticking, it's put-up or shut-up for Portland's front office.

PMG FILE PHOTO - Wade EvansonDamian Lillard holds the Portland Trail Blazers' future in his hands.

This shouldn't come as a surprise to anyone familiar with the player, franchise and the landscape of today's NBA, but it should make fans of the Blazers awfully nervous as the team's star point guard — for potentially the first time — listens to outside influences and watches closely what the powers-that-be do and say in the wake of another mediocre season.

Portland's been here before. They watched Clyde Drexler leave for greener pastures in search of the elusive championship following a trio of failed attempts in the early 1990s. Rasheed Wallace weaseled his way to Detroit when things went south in the wake of a near miss in the early 2000s, and most recently, LaMarcus Aldridge opted for San Antonio despite being teamed with a burgeoning superstar (Lillard) as a means to what he hoped would be his championship end.

It worked for two of those guys. Drexler hit the jackpot in Houston, Wallace found gold beneath his ring-chasing rainbow in Detroit, and if not for a heart condition that abruptly forced the 15-year veteran to retire after an April 10 game versus the Lakers, Aldridge may too have found greener grass on the other side in Brooklyn.

So, with nothing but a borderline all-star (C.J. McCollum), a disgruntled and slightly better-than-average post (Jusuf Nurkic), and little more than a rather fortunate trip to the Western Conference Finals in 2019 to show for it, what's keeping Lillard here other than a stubborn desire to do it the "right way?"

Nothing — and that's what should scare you the most.

Lillard's a rare breed. In an era of NBA superstars recruiting their way to a sizable edge over the field in search of easing their way to a ring, banner and legacy that puts them on the basketball map, Portland's point guard wants to earn it. Whether it's a reflection of his upbringing, his experience as a young adult, or simply a desire to go against the grain, Lillard wants to win, but he wants to do it on his terms. But while an admirable and undoubtedly respected means of attack, it may also be suicidal for a player whose career clock is ticking.

Dame will be 31 next month, just finished his ninth professional season and has played nearly another season (61 games) if you figure in his postseason career. He also rarely misses games — having played in nearly 95% of his team's regular-season contests — and notably plays hard on a night-in-and-night-out basis, meaning he's got some miles on his tires.

Additionally, he's not a big man. At 6-foot-2, 195 pounds, LeBron James he ain't. By any metric, he's small for the league, and players his size typically erode quicker than the average bear. That's not a knock on the superstar, but the reality of an undersized guard heavily dependent on the skills that allow him to thrive despite the inferior stature to do so.

That's what happened to Kobe Bryant at the end. What cut Isaiah Thomas' career short and led to the steep decline of Allen Iverson. Sure, Lillard can likely play six to eight more years if he'd like — after all, there's always room for a guy who can shoot the three. But his prime is likely but two or three more years, and who'd blame him if he chose to maximize them somewhere else?

Enter the Trail Blazers organization. That's their job: to maximize the return on Lillard's investment. And to this point, they've done nothing more than a fair to middling job doing it.

I'm not going to sit here and act like they've been an embarrassment. That would be a hot take with nothing more than an agenda in mind.

They've drafted pieces like McCollum, traded for Nurkic, and made mid- and off-season deals with lofty goals in mind. But their intent has proven greater than their aptitude, and for that, when it comes to failing their point guard — they're guilty as charged.

General manager Neil Olshey needs to go, head coach Terry Stotts did too and already has, and some way, somehow they need to convince, trick or, hell, coerce a superstar into joining Dame in the Rose City.

We know it, Lillard does now too, and so does the rest of the league who'll be working to convince him it can't happen. And opposed to in years past, I think he now may be listening.

The guy wants to win, and I firmly believe he wants to do so here. But with every passing disappointment, his mortality, his team's futility, and the reality of the situation hit closer to home.

Drexler knew it, so did Wallace, and Aldridge too. But Dame's always gone against the odds — and that might be Portland's only hope.

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