MIL
Perhaps the Bucks need to trade Middleton. While he is all-around talented, he might not be the perfect fit alongside Giannis. The Bucks acquire a more dynamic offensive player in CJ McCollum, along with the defensive ace, Derrick Jones Jr. Who has improved his jump shot dramatically over the last few days. McCollum is also one of the clutches players in the league, his skills will be very much needed in the playoffs. Also, McCollum has improved his range and defense dramatically this year. Having a backcourt of Holiday and McCollum would provide the Bucks with an elite offensive and defensive game.
Jrue Holiday - CJ McCollum - Derrick Jones Jr - Giannis Antetokounmpo - Brook Lopez OR
Jrue Holiday - CJ McCollum - Giannis Antetokounmpo - Bobby Portis - Brook Lopez
POR
The Blazers have proven to be a consistent threat every year, but every year they face the same problems. Defense. With this trade, the Blazers acquire two all-NBA defenders. Middleton and Oladipo provide a different, yet consistent offense and they might be a better fit alongside Dame than McCollum.
Damian Lillard - Victor Oladpio - Khris Middleton - Robert Covington - Jusuf Nurkic.
HOU
The Rockets continue down the rebuild road and get two young prospects in which they can develop. Also, the two first-round picks sweeten the deal.