In a stunning offseason move, the Milwaukee Bucks have opted to stretch-and-waive the final two years of Damian Lillard’s contract, freeing up $112.6 million in cap space and officially closing the book on a star partnership that never fully materialized. Now, the Bucks are aggressively retooling their roster, particularly the backcourt, and a familiar face could be on the horizon.

With the cap flexibility gained from Lillard’s departure, Milwaukee quickly signed free-agent big man Myles Turner from the Indiana Pacers. Turner, a defensive anchor and proven floor spacer, is expected to slot in seamlessly with the Bucks’ core, adding a fresh 3-and-D dynamic to the frontcourt.

Meanwhile, Milwaukee has already secured a trio of returning guards—Kevin Porter Jr., Gary Trent Jr., and Ryan Rollins—while adding veteran Gary Harris in a depth role. Still, with Andre Jackson Jr.’s 2025-26 contract decision deferred until opening night, it’s clear the Bucks are leaving the door open for more moves in the backcourt.

Rumours continue to swirl around Milwaukee’s possible pursuit of marquee free agents like Chris Paul and Bradley Beal, but there’s also a strong case to be made for a more economical and emotionally resonant option: Malcolm Brogdon.

Drafted by the Bucks in 2016 with the No. 36 overall pick, Brogdon defied the odds to win Rookie of the Year, outshining higher-drafted peers like Jaylen Brown, Pascal Siakam, and Domantas Sabonis. His two-way presence and maturity made him an instant contributor on a playoff team.

Since leaving Milwaukee in a sign-and-trade to Indiana in 2019, Brogdon has battled injuries, missing an average of 31.2 games per season. Despite those setbacks, he proved his worth again in 2022–23 with the Boston Celtics, winning Sixth Man of the Year before being traded twice—first to Portland and then to Washington.

Now 32, Brogdon is coming off a shortened season with the Wizards, where he averaged 12.7 points, 4.1 assists, and 3.8 rebounds in just 24 games. Though his three-point shooting dipped to 28.6% last year, his career average of 38.8% suggests it could rebound in a smaller role.

Available likely on a veteran’s minimum deal, Brogdon could offer Milwaukee cost-effective scoring, passing, and leadership off the bench. More importantly, he could provide much-needed stability in a reshaped backcourt without the financial risk.

As the Bucks look to remain contenders post-Lillard, a reunion with Brogdon might be the low-risk, high-reward move that helps steady the ship.