Photo: Peter Baba

The Milwaukee Bucks are gearing up for an aggressive offseason strategy, aiming to shore up Giannis Antetokounmpo’s support cast through trades and free agency, according to ESPN.

This urgency stems from three straight first-round playoff exits, despite investing nearly $940 million in salaries and luxury taxes over the past four years – a hefty price tag with limited postseason success.

Milwaukee’s rebuilding efforts have been hampered by a depleted farm system. The team has traded away its first- and second-round draft picks for the next six years, leaving little room for talent infusion through the draft.

That puts added emphasis on strategic signings and shrewd trades to balance the aging core.

Without the draft, the Bucks are preparing to deploy their available $14.1 million non-taxpayer midlevel exception and $5.1 million bi-annual exception – assets freed up by the recent Khris Middleton–Kyle Kuzma trade.

These exceptions could help re-sign contributors like Gary Trent Jr. or potentially bring in a veteran guard to step in for Damian Lillard, who is expected to miss significant time after tearing his left Achilles in April.

Despite his injury, Lillard is under contract for $54 million next season, further squeezing Milwaukee’s cap space, already strained with 79% committed to Antetokounmpo, Lillard, and Kuzma.

Amid these constraints, Pat Connaughton’s $9.4 million expiring contract remains the Bucks’ lone sizable trade chip.

Under current NBA rules, however, they can’t bundle that with smaller deals to land a single $25 million-plus player, limiting their ability to orchestrate a major acquisition without creative maneuvering.

That likely means Milwaukee may lean toward sign-and-trade scenarios, using veterans like Brook Lopez or Bobby Portis (should Portis decline his option) to create flexibility.

The Kuzma trade also brought in traded-player exceptions that can be “stacked” once they fully enter the picture, potentially enabling bigger moves later.

Milwaukee’s offseason will be a navigation test, turning financial constraints into constructive roster decisions while ensuring Giannis remains competitive in the short term.