5 Trades to fill Milwaukee Bucks' biggest hole

The Bucks must improve their roster if they want to win the championship.
Milwaukee Bucks, Damian Lillard, Giannis Antetokounmpo
Milwaukee Bucks, Damian Lillard, Giannis Antetokounmpo / Benny Sieu-USA TODAY Sports
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2. Blazers give up defensive ace

Portland traded Damian Lillard and began a rebuild this offseason. They have a young backcourt of Scoot Henderson, Anfernee Simons, and Shaedon Sharpe. The Blazers also acquired Deandre Ayton and signed Jerami Grant to a massive contract. Even with some early season injuries, Thybulle is playing just over 20 minutes per game, despite starting nine of 11 contests.

Portland matched a three-year $33 million offer sheet Thybulle signed with the Mavericks in restricted free agency, but that does not prevent him from being traded. The two-time All-Defensive wing wants more run and could be on the move before the deadline. The Bucks and Blazers just made a trade and could link up for a second deal.

Bucks-Blazers swap

The Bucks are limited in what they can offer. They only have two second-round picks, but could add in some secondary first-round pick swaps. Thybulle fetched just two second-rounders and Jalen McDaniels when he was shipped from Philadelphia to Rip City at last year’s deadline as an expiring contract.

The Blazers could try to flip Connaughton and cut Payne. They would get back their 2024 second-round pick from Milwaukee, which figures to be in the 30s, plus a Bucks 2027 second.

Good luck scoring on a unit featuring Giannis Antetokounmpo, Brook Lopez, Thybulle, and a healthy Khris Middleton. Damian Lillard is a subpar defender, but that group figures to produce outstanding numbers.