Khris Middleton Explains What It Was Like to Lose Jrue Holiday in the Damian Lillard Trade with the Milwaukee Bucks

It’s been nearly two months since the Milwaukee Bucks completed their blockbuster Damian Lillard trade, which forced the team to give up Jrue Holiday as part of the transaction. It was not an easy decision to make, but it was one that the Bucks had to make in order to obtain Dame.

Khris Middleton Reflects on the Damian Lillard Trade with the Milwaukee Bucks

2023 NBA Free Agency: Khris Middleton's Potential Teams

Milwaukee forward Khris M (22) drives downcourt in the third quarter of a game against the Indiana Pacers at Fiserv Forum on March 16, 2023. Benny Sieu-USA TODAY Sports is required to provide credit.
Khris Middleton vividly recalls that exact moment. When he first learned about the Lillard trade, the three-time All-Star was overtaken with emotion, according to him:

“I just got done with a workout session. I would say it’s just mixed emotions,” Middleton said, via Jim Owczarski of the Milwaukee Journal Sentinel. “First, not knowing if it was really real or not because it came out the blue. Then it’s tough to see our guy go. What he did for our organization as he did for me as a person and my family. It was tough to have that conversation to see him go the other way. But to get somebody like Dame in, you gotta be excited or a guy like that.”

As Middleton stated, it’s difficult not to become excited about the thought of collaborating with Lillard. He couldn’t help but feel awful about losing his friend as part of the agreement.

Holiday only played for the Bucks for three seasons, which isn’t exactly a lengthy time. The five-time All-Defense guard, on the other hand, not only established himself as a major player on the team, but he also formed some enduring ties with his teammates.

Milwaukee Bucks stars Khris Middleton and Jrue HolidayApr 8, 2022; Detroit, Michigan, USA; Milwaukee forward Khris M (22) smiles from the bench with guard Jrue H (21) during the fourth quarter at Little Caesars Arena. Mandatory Credit: Raj Mehta-USA TODAY Sports

At the end of the day, however, you can’t really say that the Bucks did not mark a massive win with their trade for Lillard. However, this does not make losing Holiday any easier.

Nov 11, 2023; Orlando, Florida, USA; Milwaukee Bucks guard Damian Lillard (0) talks with Milwaukee Bucks forward Khris Middleton (22) during the second half against the Orlando Magic at Amway Center. Mandatory Credit: Matt Pendleton-USA TODAY Sports

Milwaukee guard Damian L (0) discusses with Milwaukee forward Khris M (22) during the second half against the Orlando Magic at Amway Center on November 11, 2023. Credit: Matt Pendleton-USA TODAY Sports For More Wisconsin Sports:
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