1. Milwaukee Bucks
This one speaks for itself. A Buck for nearly his entire career, Khris Middleton has grown fond of Milwaukee and vice versa. He’s developed into a near-perfect side kick to Antetokounmpo and the team’s expectations are NBA Finals or bust now that it’s experienced playoff success.
Because Milwaukee retains the rights to Middleton, it can go over the salary cap in order to re-sign him. Ridding themselves of George Hill’s lofty cap number (waiving him saves $17 million in 2019) would go a long way towards signing Middleton. The team can also go over the cap to bring back Brogdon, Lopez and Mirotic.
Should Milwaukee decide to lock up both Brogdon and Middleton long-term, it would be committing a lot of its salary cap to those two players. In addition to that, Antetokounmpo’s contract extension will undoubtedly be for the super-max. It’s possible to work out in terms of numbers, but it’ll tie up the hands of the front office when it comes to other impact free agent signings.
Middleton is familiar with the system and has been proven to thrive under Mike Budenholzer’s tutelage. Still young enough to have his prime coincide with most of his upcoming contract, it may be in his best interests to stay where he’s comfortable and not have to prove himself all over again.