Caldwell-Pope has two championships under his belt, winning one with the Los Angeles Lakers in 2020 and one with the Denver Nuggets in 2023. He was a pivotal player for both teams. He’s coming off a sub-par season with the Orlando Magic and has two years left in his $66 million contract.

Following an All-Star caliber season, Damian Lillard tore his Achilles tendon in Game 4 against the Pacers, knocking him out for the rest of the playoffs and possibly the 2025-26 season.

If he had not torn his Achilles, there was a chance Bucks star Damian Lillard would have heard his name in a ton of trade rumors.