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Are Blazers ready to make biggest commitment in franchise history?

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Lillard looks back at the Blazers' season (1:50)

Damian Lillard calls the Blazers' season 'special' after everything that they've gone through. (1:50)

Portland Trail Blazers fans fell in love all over again with their team this season, from the breathtaking performances of their star guards to the toughness of their role players to the mere presence of their wounded center in the playoffs.

The end against the Golden State Warriors was bitter. Even as they admired watching the champs work, all in the Rose City will mutter, "they could've been up 2-1, you know" for years into the future. Nonetheless, despite the sweep, it was an inspired playoff run that generally warmed the region.

After decompression, though, there are going to be a few possibly stressful issues that will confront the organization.

At the heart is this: There's a queue of Blazers who are in line to be paid, and it isn't clear if ownership will foot the bill or even keep the team.

Among those who are in position for an extension are Damian Lillard, CJ McCollum, coach Terry Stotts and maybe even president of basketball operations Neil Olshey. Then there are free agents Al-Farouq Aminu, Rodney Hood, Enes Kanter, Seth Curry and Jake Layman.

Last Oct. 15, just three days before the start of the season, longtime Blazers owner Paul Allen died. This was a devastating blow to the entire Pacific Northwest, where Allen wasn't just a billionaire owner of the Blazers and Seattle Seahawks but a philanthropist and businessman who positively affected the lives of many.

Allen had been sick with cancer, but his passing was still disorienting because he'd beaten the disease before. Just two weeks before his death, he had announced that the cancer had returned and that doctors were optimistic he'd see good results from treatment.

His sister Jody Allen is the lone heir to his massive estate, making her the Blazers owner now. She has not shown a great interest in the team and didn't attend a game until April, when she came to see the team break a long-forgotten 10-game playoff losing streak. The franchise is being led day-to-day by vice chairman Bert Kolde, Paul Allen's close friend and business associate who has held the role since 1988.

Paul Allen ran the Blazers like a fan, pouring in money over the years. He spent more than $100 million on luxury taxes alone, an outsized number for a small market like Portland. He loved the draft and bought so many draft picks over the years that it contributed to the NBA capping the amount teams could spend to purchase them.

Though he'd become more judicious with his spending over the past decade, the team had the league's fourth-highest payroll this season at more than $130 million, not including a $15 million luxury-tax charge.

But it's unclear if Jody Allen will authorize future spending deep into the luxury tax. Those in the organization have been told there are no changes planned in the short term but there's been little offered beyond that. There is a possibility the team could be prepared to be put on the market, and typically that might mean controlling payroll.

A number of players' contracts expire in 2020, when the team's books would potentially be cleaned up (especially if they have a quiet summer).

In the coming days, Lillard will officially be named to the All-NBA team for the second straight season, making him eligible for a supermax contract extension. A bona fide in-his-prime superstar, he's under contract until 2021.

Stars like James Harden, Russell Westbrook and John Wall were in this position and extended their deals two years ahead of free agency. If the Blazers offer -- and all signs point toward them doing so, though there would be deal points to negotiate -- Lillard will be able to add four years and about $191 million to his contact starting July 1. That would put him under contract for the next six seasons for a total of $256 million, a deal that will likely finish out his prime.

However, Lillard has the option of waiting a season because he will now be eligible to sign a supermax in the summer of 2020 as well. At that time, he'd be in position to add five years and $247 million to his deal to create a six-year, $277 million deal that would project to be the richest in NBA history.

You can see the difference in the numbers that waiting a year would make. With uncertain ownership, you could make a case that he should wait. That said, Lillard is at ease with the ownership and is open to extending this summer, sources said. Soon to be 29, Lillard has expressed an interest in locking himself in, as he and his family are settled in Portland.

McCollum also can extend this summer. Like Lillard, he has two years and $57 million left on his contract. The Blazers could offer McCollum three years and up to $114 million in an extension. This is a big decision for both sides because McCollum could make significantly more if he waits but it's also the kind of outlay that would take a major commitment from ownership long term.

Elsewhere, Olshey did a fantastic job putting the team together this season, but he's not likely going to be able to keep it. With the Blazers already over the cap for next season, they will be limited players in free agency, even before ownership directives are clear. Complicating matters further, they don't have full rights on Curry, Hood or Kanter and will likely only have the $5.7 million taxpayer midlevel to use.

The Blazers may try to ease their salary situation by moving Meyers Leonard, who's had some moments in these playoffs, but they've been trying that one for years now and no one has been too interested.

Meanwhile, Stotts has one year left on his contract. He reportedly preferred to land an extension last summer but after a disappointing performance in the playoffs in 2018, it was not granted. One of the league's longest-tenured coaches, he's earned security. So, perhaps, has Olshey, who has two years left on his deal.

There are a lot of decisions to be made. But ultimately the Blazers are going to retain their best players and there's optimism that Jusuf Nurkic is already recovering well from his terrible broken leg. It's been easy to forget how much they accomplished without him.

With the face of the West maybe changing as Kevin Durant decides on free agency, they are well positioned to remain among the contenders next year.