2. Trade Lopez and Holiday to sign Siakam in free agency
Remaking their roster is difficult. Jrue Holiday has a $39.4 million player option for next summer, but it sounds like he plans to opt in. He mentioned retiring in two years after his current contract expires in an April podcast interview. If he stays on the Bucks books, they must trade two of their four best players to free up cap space.
Milwaukee could look to move on Brook Lopez and Holiday with one left on his contract. It would drop $62.4 million off their books and give them roughly $30 million to spend in free agency. It is not a maximum salary slot, but a hefty chunk of money to offer a veteran.
The Bucks would have to take some money back in trades but could look to dump Pat Connaughton or Bobby Portis to clear additional room. If they can find the right deals, Milwaukee could come out with enough cap room to sign Pascal Siakam and a few draft picks to further upgrade their roster. It would take Lopez and Holiday remaining at the top of their games this season. They have zero signs of decline, but it is no certainty as both are north of 30.
This would be a desperate move by the Milwaukee Bucks and one that could blow up in their faces in multiple ways. If it convinces Giannis Antetokounmpo to sign long-term, it would be worth the gamble.