5. Damian Lillard
You knew this one was coming. Listen, we know that he will only play for the Miami Heat. We know that. But we also know that what Lillard really wants is to be on a title team. And if a few more months of Lillard’s prime go by without him being traded to the Heat, he might be willing to broaden his list of destinations.
And what better place for Lillard to go to instead of Miami than the team that currently rosters his longtime backcourt running mate, CJ McCollum. I’m sure Lillard could get over his fixation with South Beach if it meant a chance to finish what he and McCollum started all those years ago.
If the Pelicans can complete this hypothetical midseason deal, they give Lillard and McCollum a better team than any roster they ever had in Portland. And considering what the Heat have been offering the Trail Blazers, it is very possible that the Pelicans can come up with a better package that doesn’t include Ingram, Williamson, and McCollum.
Despite being older, Lillard will cost more than Siakam. But Lillard is also a better player than Siakam at this point in time. In fact, if he plays the way he did in 2022-23, he’d be the Pelicans best player. And if the whole core can stay healthy, he’d have his best shot yet at chasing his first-ever NBA title.