Obviously the Blazers would be the ones getting the return, not the Bucks
Anyway,
Before thinking about where Jrue should go, it's important to realize what Portland will want for him: expiring contracts and picks. So let's break it down.
Jrue Holiday for Kevin Huerter, Harrison Barnes, and one first.
This gives Sacramento a desperately-needed point-of-attack defender to instantly bolster their lackluster defense.
Kevin Huerter for Gary Harris and a lightly-protected Denver first.
The pick will almost certainly be in the 25-30 range, but Harris's expiring contract provides its own benefit to Portland, as they start their rebuild with Anfernee Simons, Jerami Grant, & DeAndre Ayton combining for $84M in salary just this year. As for Orlando, they're clearly prioritizing positional size, so a 6'7 SG who can shoot the ball as good as anyone not named Steph would be huge for them.
Harrison Barnes for Evan Fournier and two seconds.
Fournier is, of course, an expiring contract. Technically there's a team option for text year but we all know that's being declined. As for New York, they get a backup PF who can play SF in any big lineups they'll have to run to compete with the size of teams like Boston and Milwaukee. But also, they give up two seconds and someone who isn't good at basketball for someone who is good at basketball. That sounds good to me.
Total Return: Two expiring contracts, two firsts, and two seconds for Jrue Holiday. Not bad at all.
Kings's Rotation:
De'Aaron Fox // Davion Mitchell
Jrue Holiday // Malik Monk
Keegan Murray // Chris Duarte
Trey Lyles // Kessler Edwards
Domantas Sabonis // JaVale McGee
Magic's Rotation:
Markelle Fultz // Cole Anthony
Kevin Huerter // Anthony Black
Franz Wagner // Jett Howard
Paolo Banchero // Chuma Okeke
Wendell Carter Jr. // Moritz Wagner
Knicks's Rotation:
Jalen Brunson // Immanuel Quickley
Quentin Grimes // Donte DiVincenzo
RJ Barrett // Josh Hart
Julius Randle // Harrison Barnes
Mitchell Robinson // Isaiah Hartenstein
Blazers's Rotation
Scoot Henderson // Shaedon Sharpe
Anfernee Simons // Evan Fournier
Matisse Thybulle // Gary Harris
Jerami Grant // Kris Murray
DeAndre Ayton // Moses Brown