Grading the Milwaukee Bucks’ shocking acquisition of Damian Lillard

Milwaukee Bucks, Damian Lillard, Jrue Holiday. Mandatory Credit: Jaime Valdez-USA TODAY Sports
Milwaukee Bucks, Damian Lillard, Jrue Holiday. Mandatory Credit: Jaime Valdez-USA TODAY Sports /
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Milwaukee Bucks: Jrue Holiday, Portland Trail Blazers: Damian Lillard
PORTLAND, OREGON (Photo by Abbie Parr/Getty Images) /

What the Milwaukee Bucks traded away in the Damian Lillard deal.

As part of the three-team deal, the Bucks traded Jrue Holiday, two pick swaps, and an unprotected 2029 first-round pick to Portland. The team also moved Grayson to Phoenix as part of the trade.

Trading away Grayson Allen is a footnote on this trade because while Allen showed signs of being a knockdown 3-point shooter, he wasn’t consistent enough offensively, and he didn’t defend at an elite level. Trading away Jrue Holiday was a tough decision to make.

The NBA is a brutal business, and Milwaukee had to trade away Jrue Holiday, who expressed a desire to finish his career with the team. That’s what makes this trade so hard.

The draft picks aren’t an important part of the equation because Milwaukee is still in a championship window, and they don’t need to stockpile young players for this veteran roster.

In 2020, General Manager Jon Horst made the swing of the century by acquiring Holiday for Eric Bledsoe and draft picks. In his first year with the team, Holiday helped Milwaukee capture their first title in 50 years by being a part of the greatest play in franchise history.

Known as the “Valley Oop,” the Bucks were up 120-119 with less than 20 seconds left when Holiday stole the ball from Devin Booker and raced up the floor most point guards would have pulled the ball out and waited to be fouled instead, Holiday sees Giannis Antetokounmpo get behind the defense and throws a risky alley-oop pass that everyone thought was too high, but Giannis jammed it with two hands and drew an and-one from Mikal Bridges. Thus, the Valley-Oop lived in infamy as one of the defining moments of the Bucks’ championship run.

During his time in Milwaukee, pundits started to take notice of how good of a player Jrue Holiday is. He became one of the best two-way players in the NBA, and he helped turn Milwaukee from a team that was known as only being good in the regular season to a team that was talked about as a championship contender every year.