Milwaukee Bucks
Best contract: Bobby Portis (2-years, $26 million)
It would be easy to place Giannis Antetokounmpo in this spot considering he's arguably the best player in the league. However, the Bucks are going to be paying Giannis nearly $80 million during the 2027-28 season. Before we categorize that deal as the "best" on the team, we must wait to see how much the NBA's salary cap is set to grow over the next few years. One contract that is clearly good for the Bucks at the moment, no ifs, ands, or buts, is the two-year, $26 million deal that Bobby Portis has remaining on his deal.
Portis is a valuable rotation piece for the Bucks and would be easily tradable if that's something the Bucks needed to explore during the offseason.
Worst contract: Damian Lillard (3-years, $170 million)
It's easy to see why the Milwaukee Bucks went all-in on Damian Lillard during the offseason. However, there's a case to be made that he hasn't played up to his potential this season in Milwaukee. Considering he's climbing in age, this contract could get pretty bad for the Bucks very soon.
It's been less than one year and it'd be crazy to count Lillard out, but his performance in the postseason is going to be key.