For Orlando, the motivation is clear. The Magic are in desperate need of a true floor general. Despite boasting a promising young core led by Paolo Banchero and Franz Wagner, their offense remains one of the most inefficient in the league, ranking 27th overall and dead last in three-pointers made per game. Neither Jalen Suggs nor Anthony Black has developed into the kind of lead playmaker that can elevate the Magic in a deep playoff run. Damian Lillard, however, is exactly that: a dynamic scorer, elite shooter, and proven leader with deep postseason experience. Adding Lillard would instantly boost Orlando’s offensive ceiling while spacing the floor for Banchero and Wagner to thrive.

His presence alone would force defenses to adjust and could help transform Orlando’s current defensive-minded, grind-it-out identity into a more balanced, playoff-ready team. His shot creation and gravity are exactly what this team has lacked. From Milwaukee’s perspective, the proposal comes at a moment of uncertainty. The Bucks are currently down 2-0 to the Indiana Pacers in the first round of the playoffs, with Lillard came back from a right calf blood clot, the Bucks are in a precarious position.

Injuries have plagued their season, and the core of Lillard, Giannis Antetokounmpo, and Brook Lopez, though formidable on paper, has yet to deliver consistent dominance. Lopez is aging, and Milwaukee’s roster depth has taken a major hit since the Jrue Holiday trade.

Swartz’s proposed deal offers the Bucks a reset button, not a rebuild, but a reload. Jalen Suggs, 23, is one of the league’s most tenacious on-ball defenders, and Wendell Carter Jr. offers a reliable interior presence and spacing ability at center, especially if Lopez departs. Cole Anthony is an explosive scorer off the bench who could thrive in a fast-paced second unit. Crucially, the Bucks would also regain a 2025 first-round pick, re-entering a draft they currently owe to the Nets.

Still, the timing of such a move would raise eyebrows. Milwaukee gave up a king’s ransom to acquire Lillard just one year ago, a package that included Jrue Holiday, Grayson Allen, and multiple first-round picks.

After a season of injuries and adjustments, it feels premature to break up the experiment before seeing a healthy postseason run. Lillard, averaging 24.9 points and 7.1 assists on elite shooting splits this year, remains a lethal weapon next to Giannis when both are fully healthy.

Milwaukee may have to ask a difficult question: is doubling down on Lillard the right move, or is it time to pivot while Giannis is still in his prime?