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The will they, won't they saga that has been Damian Lillard's time with the Portland Trail Blazers recently may be coming to a peak when NBA free agency begins on Friday, June 30. Lillard has been adamant that he wants the Blazers to add veteran players that will immediately help Portland contend for a championship. It was even reported leading up to the NBA Draft that took place last Thursday that Portland was looking to trade the No. 3 overall pick to try and go after another star-level player that could immediately make an impact. 

Instead, the Blazers drafted highly touted prospect Scoot Henderson, and while they should be thrilled about landing the young guard, the potential of Lillard requesting a trade looms over Portland.

With this potential fork in the road that the Blazers face as free agency nears, Lillard is expected to meet with Portland's front office sometime Monday to discuss the roster and the franchise's plan going forward, per Bleacher Report's Chris Haynes. It's unclear what will come out of that meeting, but Amick reports that Lillard's stance on bringing in high-level talent has not changed, which puts the Blazers in a tricky spot moving forward. 

If Lillard feels like the Blazers can't do enough to turn this team into a contender quickly, there's been the constant rumors of him potentially requesting a trade, with one team at the top of the list: the Miami Heat. Lillard has publicly talked about how the Heat would be amongst his preferred destinations, and after falling short yet again in the NBA Finals, Miami would certainly be enthused by the idea of a roster that had Lillard in addition to Jimmy Butler and Bam Adebayo. Lillard is said to have "serious interest" in joining the Heat, per Amick.

The question is, will Lillard finally request a trade after stoking the flames of the rumor for the last few months? And, will the Heat be able to offer an enticing enough package to the Blazers that would make them say yes? If the first thing happens, then the Heat surely won't be the only team looking to add the All-Star guard, but given that Lillard already said he would want to play for the Heat, it kind of puts Portland in a tough spot to fulfill his wishes after years of loyalty to the franchise.

There's also the possibility that Lillard could come out of his meeting with the Blazers front office with the confidence that the team will try their best to surround him with better talent. If that happens, then the Blazers will have to make good on that promise. Because if that doesn't happen, and Portland once again struggles next season, Lillard could request a trade at February's deadline.

We'll have to see how this meeting pans out for both sides, but either way the Blazers will have a busy offseason with a lot of questions to answer.