The offseason is now just 12 days away, with free agency starting on August 2. And given the back to back 1st round exits in the playoffs, there is clearly unrest in Portland. When a superstar like Damian Lillard responds ambiguously regarding his future with the franchise, it has to be worrisome for Blazers GM Neil Olshey.

An inevitable call for 1 team, is a golden opportunity for another, and it is an opportunity that may see individuals like Pat Riley or Daryl Morey make a move. Recent reports have identified Miami, Philadelphia, the Knicks, and Houston as prime suitors for a player of Dame’s caliber.

Free agency is out of the question for Lillard, who is on contract with Portland till 2025 on a 4-year $176-million deal. And while Dame may not have complete control over his destination, 4 years’ worth of security is a lucrative enough deal for big market teams to pursue!

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While Dame quashed rumors which revolved around forcing a departure from the Blazers this offseason, he did not commit to the franchise either. Lillard left things open to the imagination when he commented, “Lot of things have been said, it hasn’t come from me. Number 1: It’s not true. Secondly… I haven’t made any firm decision on what my future will be.”

And while most of the league along with Dame himself expect Lillard to put on a Blazers uniform come opening night, he has outlined his expectations from the front office, to be “more urgent” this offseason.

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Dame is clearly not pleased with Portland’s first-round exits 2 seasons in a row. And his view on the root cause of the issue doesn’t just pertain to coaching! Lillard said on Friday, “I think if you look at our team as it is, going into next season, I don’t see how you can say ‘This is a championship team, it just needed a new coach,’ when we just lost in the first round to a team that was hurt.”

Needless to say, Philadelphia, a team with their own roster issues will be monitoring the situation closely. But therein lies the issue. Both Morey and Olshey are on different wavelengths. While Olshey will zero in on an all-star swap in CJ McCollum for Ben Simmons, Morey will be eyeing a trade that involves Dame Dolla instead.

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Following the Sixers flameout against Atlanta, the front office will be itching to bring in reinforcements. Shipping off Simmons in a trade deal remains an option as Morey looks to capitalize on an injury-prone Embiid’s prime.

McCollum for Simmons makes sense for both franchises. While it helps boost CJ’s facilitation and scoring ability, partnering with Joel Embiid also provides him capitalization on his perimeter shooting, a facet where he averages over 40%!

Could playing as the main 3-pt marksman on a roster be just what the doctor ordered for CJ?

Simmons’ shooting won’t be a concern for Portland, given his All-NBA defense and facilitation ability that will see Portland’s defensive rating jump higher than 2nd last in the league.

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Portland’s future

If a trade deal is finalized, the Portland Trail Blazers will need to look at bringing back Norm Powell as a priority, given Ben Simmons’ skill set. Powell is close to a 50/40/90 shooter, providing a direct replacement for McCollum if he chooses to re-sign.

Considering that injuries have defined most of the season, this offseason will be highly anticipated. In a free agency class that lacks the wow factor, a not-so-promising trade market, and a hard cap threat, the Blazers front office must make some tough choices.

With a star like Dame Lillard who may start wanting out soon, the rest of the league is on the prowl. With the curtain coming down quick, what lies ahead for GM Neil Olshey?

Watch this story – Damian Lillard, Ben Simmons & Other NBA Players Who Will Be Trending During Trade Talks