3 teams besides the Heat who should consider risking it all for Damian Lillard

No. 2 team that should trade for Damian Lillard: Milwaukee Bucks

The Bucks are the favorites to win the East next season. There’s some lingering uncertainty after last season’s first round flameout, but Giannis Antetokounmpo, Khris Middleton, and Jrue Holiday are still on the roster. That’s enough to give any group more than a puncher’s chance at the title.

Of course, Milwaukee would be foolish not to consider more than marginal changes to the roster. New head coach Adrian Griffin figures to imbue the team with new principles and approaches. Maybe even better ones than Mike Budenholzer, who never could entirely shed his reputation for stubbornness in the playoffs.

In the end, however, the Bucks’ inability to topple Miami was roster-based, not coaching-based. The Bucks have long been prone to stalling offensively in the halfcourt. Last season was especially problematic with Khris Middleton operating at half-strength. Hopefully Middleton is back to regular form in 2023-24, but the Bucks should note their propensity to go ice-cold from 3-point range and consider, maybe we should trade for the top-20 player who takes a lot of 3s. 

Lillard would completely revamp the offense around Giannis. Those pick-and-roll actions would leave even the best defensive teams utterly confounded. It’s like Zion-Lillard on steroids, with Giannis bludgeoning defenses in the paint while Lillard stretches them thin on the perimeter. Presumably Khris Middleton, who can’t be traded after signing his new contract, would feast on plenty of open 3s and clean driving lanes.

Any trade would probably have to start with Jrue Holiday, who the Blazers may not want depending on Joe Cronin’s immediate goals in Portland. A third team, however, would not be hard to find. Holiday is valued all over the league for his defensive intensity and wonderful personality. If Milwaukee can fashion a trade around the few draft picks and young players at their disposal, plus whatever the haul is from a separate Holiday trade, that could push them over the Heat’s current offer.

It’s a stretch, but the Bucks need a shake-up and Lillard would make them overwhelming favorites in the East. It may represent his best chance to compete for a championship, which is ultimately his guiding desire — even if he’d prefer to live in Miami instead of Milwaukee while doing it.