Milwaukee Bucks Could Pursue Damian Lillard’s Ex-Teammate of 5 Years After Latest Report from Boston

Last season in Portland, Simons averaged 19.3 points and 4.8 assists on 42.6/36.3/90.2% shooting splits. Compared to 2024 and ’23, he had something of a down year in both volume and efficiency. Defense is an issue. Simons is also on expiring contract, making him a one-year rental. There’s a reason Portland made him available.

Nonetheless, Simons is good at what he does – scoring – and the Bucks could use that. Do they have the pieces to get a deal done?

They do in theory. For the reasons cited above, he isn’t an expensive target. Boston is looking to unload him mostly for salary concerns, or so it seems. Any Bucks package would likely revolve around Kyle Kuzma, the most logical matching salary.

Financially, taking back Kuzma would benefit the Celtics by itself, giving them an additional $4.7 million in cap space. They would creep closer to sneaking below the first apron.

That consideration alone, however, probably isn’t enough to entice them. Kuzma has two years remaining to Simons’ one, extending his impact on the books. Jayson Tatum should be back by 2026-27; carrying unwanted salary then isn’t in Boston’s favor. The Bucks would have to sweeten the pot.

Kuzma Package Would Be Problematic for Celtics

With what, though? They don’t have much young talent to send out, and anyway they shouldn’t consider doing so for a one-year rental, sub-All-Star acquisition like Simons. Milwaukee could attach a small salary like Chris Livingston or Andre Jackson, which Boston could absorb via trade exception, but that doesn’t move the needle.

Would a 2031 second-rounder suffice? Maybe, but the Celtics would still be taking on Kuzma, who as a poor shooter is the antithesis of their organizational philosophy. Simply put, he would be a terrible fit in Boston. They might be waving the white flag on next season, but Kuzma’s contract carries over. Because of this, Kuzma plus “X player” plus a second-round pick might not intrigue them, despite Simons’ flaws and expiring deal.