Eric Bledsoe trade and 7 other regrettable Bucks moves Jon Horst botched

6. Dame trade

Putting the Damian Lillard deal on the list could look foolish, especially if the Bucks win a championship with him as their starting point guard. Early returns showed Milwaukee may have been better off with Jrue Holiday. This trade cost the Bucks a ton. Giannis pushed the Bucks to improve their roster, so Horst made it happen, but all sides may regret this move in a few years.

Lillard is a future Hall of Famer and one of the 75 greatest players of all time. This is no knock on him, but the acquisition cost the Bucks Holiday, Grayson Allen, one first-rounder, and two pick swaps.

They missed Holiday’s lockdown defense and Allen’s elite shooting. Things went from bad to worse when the Blazers traded Holiday to the rival Celtics. He was second-team All-Defense, and Allen led the league in 3-point percentage this season. Both would have helped Milwaukee navigate a difficult season.

Lillard put up outstanding numbers, but his defense is an issue. The 33-year-old undersized guard is locked at a massive salary until 2027. The Bucks are not trading him for a star return and need elite production if they are going to win another championship. Lillard’s defense is even more problematic in the playoffs and will only get worse as he ages. Trouble could brew quickly if Dame takes a step backward.