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.

Before star point guard Damian Lillard tore his Achilles tendon in Game 4 of their first-round series loss to the Indiana Pacers, the Milwaukee Bucks reportedly planned to explore whether it would've been best to trade him this offseason.