Wild Trade Proposal Sees Bucks Sends Damian Lillard to East Rival

The Milwaukee Bucks' season ended abruptly once again. For the third consecutive season, the Bucks' season came to an end in the first round.

As of late, the Bucks have had so many shortcomings that many have come to question whether big changes should be on the horizon this summer. That is the expectation for the Bucks prior to the 2025-26 season.

While many expect that the Bucks could part away with their superstar forward, Giannis Antetokounmpo, this trade proposal sees them part ways with their superstar guard Damian Lillard.

Eddie Bitar of Fadeaway Sports made three trade proposals; this once saw Lillard land in Flordia with the Orlando Magic.

Orlando Magic Receive: Damian Lillard

Milwaukee Bucks Receive: Jalen Suggs, Kentavious Caldwell-Pope, 2026 First-Round Pick (ORL), 2027 First-Round Pick (ORL), 2025 Second-Round Pick (ORL), 2026 Second-Round Pick (ORL)

"Milwaukee, meanwhile, would get back an ideal piece in Jalen Suggs, who has finally emerged as an elite defensive guard this season. Suggs averaged 16.2 points, 3.7 assists, and 1.5 steals per game in 2024-25 while locking up opposing guards on a nightly basis, exactly the kind of gritty, two-way player the Bucks love.

"Kentavious Caldwell-Pope, a proven 3-and-D veteran and two-time NBA champion, brings playoff experience and floor spacing (career 36.7% 3-point shooter). Add in two first-round picks and two seconds, and Milwaukee would suddenly have a treasure chest of assets while still staying competitive.

"This trade would mark a clear pivot for the Bucks: out with the aging stars, in with tough, defense-first guards and more shooting around Giannis. For Orlando, this is their aggressive win-now play. They’d be betting that Lillard’s injury doesn’t derail his elite shot-making and that his presence elevates Banchero and Wagner to new heights. It’s risky, but the payoff could be a deep playoff run in 2026."

While this trade would do wonders for Milwaukee and its future, the Bucks' reality of getting rid of Lillard is not realistic.

Lillard's season ended before the Bucks' season ended. He tore his Achilles in Game 4 of the first round against the Indiana Pacers. His trade value is close to zero as things stand; however, the conversation could be different as Lillard gets closer to health.

The real upside for Milwaukee in this proposed deal lies in the pair of first-round draft picks. Currently, without control of their own first-round selection until 2031, the Bucks are in a difficult position when it comes to building for the future.

Securing one or two picks in a trade could be the first step toward reshaping the roster and regaining long-term flexibility.

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