29. Milwaukee Bucks
Let’s be clear, it would be a horrendous fit if Simmons would be traded to the Milwaukee Bucks. They’re not ever going to trade Giannis Antetokounmpo and the fit between him and Simmons would be awful. Khris Middleton is probably off the trade block as well.
With that in mind, there’s only one trade that could land Simmons in Milwaukee. The proposed trade below works in terms of salary and talent, but it’s unlikely that either team would make the deal, especially the Bucks.
Overall, Simmons is a better player than Jrue Holiday, but Holiday is one of the best guard defenders in the league and his offense is fits Milwaukee better. He’s is a better scorer than Simmons and almost as good as a playmaker. Also having Holiday return to Philly is a nice storyline to attach to this trade.
Pat Connaughton is a better player than Shake Milton, but not by as much as some think. With that in mind, this works for Philly as they get close to the same talent returning in this trade and it’s one the franchise should consider if present, but the Bucks will never do this trade.