Interesting article on ESPN+ about Lillard looking for a record breaking extension from the Blazers in the amount of $107 million over two years when Dame will be 35 and 36 years old. Article sheds some light on the Blazers front office and ownership situations and how that may affect Lillard and his future in Portland. It's behind a paywall so here it is:

Once Portland Trail Blazers star Damian Lillard stopped threatening to request a trade, everyone understood his inevitable moment of truth: His future remained bound to the summer of 2022, not 2021. Extensions were always automatic for him, and that's no longer the case.

Lillard wants a two-year, $107 million extension in July, and he and his agent need the next general manager to sell ownership on the idea. As much as anything, this cuts to the core of the Blazers' search process. His desire for an extension into his advanced NBA years has turned into a battle for the franchise's future, an existential threat to reshaping and redirecting the organization in a post-playoff reality.

The prospects of Portland extending Lillard, 31, beyond his $48.8 million in 2024-25 to pay him $51 million at 35 years old and $55 million at 36 threatens to turn an asset of a contract into an albatross.

As former president of basketball operations and GM Neil Olshey exits the Blazers, the process to hire his successor will soon be underway. Portland is deciding whether it will hire a firm to research and recommend candidates, sources said. Bert Kolde, the longtime ownership executive and right-hand man to the late Paul Allen, will direct the search again. He's hired several GMs in his tenure.

The Blazers will be wise to expect every candidate to come armed with two important questions: What are owner Jody Allen's plans to keep or sell the team? And more immediately, would a new GM have autonomy to rebuild the franchise not around, but without, Lillard?

In the past year, Lillard and his camp have been thwarted on leverage plays -- Jason Kidd as coach, trading CJ McCollum and four first-round picks for Ben Simmons. Most of all, they lost the confidence that the Blazers had a top basketball executive and ownership willing to give Lillard the highest single-season pay in league history at $55.3 million in 2027.

With four seasons -- including an opt-out -- left on his deal, Lillard had no leverage to choose his next team this past summer. If he had asked out, he would have gone where Portland could get the best package of young players, draft picks and salary-cap relief. Asking for New York and Philadelphia makes for dramatic storylines, but the multiple years on his deal would have emboldened several small and non-destination markets to engage with Portland's steep asking price.

Among several top-level GM candidates who fit the profile of Portland's applicant pool, there's no enthusiasm to grant Lillard his massive extension contract through the 2026-27 season. In fact, several executives told ESPN they would be far more interested in the Blazers job with ownership's blessing to move Lillard sooner than later.

Through 20 games this season, Portland's Damian Lillard is averaging 21.5 points while shooting 39.7% from the field. Lillard struggled with Team USA and has played some of the poorest basketball of his career this season. He's out for 10 days now, bothered by a recurring abdominal injury. At 31, there's no reason to believe he can't get healthy and back to an All-NBA level this season. There is reason to believe that idea isn't sustainable three, four and five years from now.

Now, Lillard's group is privately selling the idea of trading his veteran teammates with value and rebuilding around him -- on that extension. Some candidates initially believed that Lillard's reps would have input with ownership on the next GM, but that has faded quickly. Rival GMs knew they had to work directly with Olshey to get deals done with the Blazers, that he had full autonomy to make decisions. Those seeking Olshey's old job believe they need to sell themselves to ownership, not to those surrounding the star player.

Portland has faith and confidence in interim GM Joe Cronin, but soliciting offers on Robert Covington and Jusuf Nurkic is one thing -- navigating offers for Lillard is another. Do the Blazers allow Cronin to make the franchise-defining decisions in the coming months and win the job? Rival teams believe they'll have a better idea once they start talking trades in the coming weeks.

Three teams with interest in Lillard told ESPN that they are waiting on him to make an offseason trade demand before calling Portland. If Lillard asks out, they know the Blazers will lose some leverage in the asking price -- and are waiting on it. Philadelphia made an offer, but New York never did, league sources said. Lillard's reps offered mixed messages on the star's intentions to stay or go, and rival teams say that the star's camp had real concerns about Olshey's willingness to recommend the extension to ownership in 2022.

Allen isn't the typical NBA owner; her late brother Paul was a maniacal NBA fan, fully engaged on a daily basis. She is conducting the franchise's business as a caretaker of a charitable trust. If she decides to sell the team, the revenue goes to that trust. Unlike her late brother, she has no real history with Lillard -- and no sentimental attachment.

There's no shortage of billionaires trying to acquire NBA and NFL teams, and currently only the Denver Broncos are available. If a new owner isn't buying into a championship contender, they will likely prefer assets and roster flexibility.

For now, the Blazers are telling people that they'll take their time on the search, that they won't be moved by anyone's agenda. The battle lines are real on Damian Lillard's future and leverage is ever-evolving. As much as anything, this fight for control of the franchise's future is a cold, sober exercise of balancing assets and albatrosses.

Can't help but wonder if Boston is one of those 3 teams and if so, what type of package would they put together for Lillard that would clear Portland's current roster to have a clean slate and assets to help make the Blazers more attractive in a sale?