Khris Middleton is now wearing a different jersey in Washington, but his heart still carries echoes of what could’ve been in Milwaukee. In a recent conversation, the former Bucks swingman opened up about the pivotal moves that shifted the franchise’s trajectory - most notably, the blockbuster trade that brought Damian Lillard to town and sent Jrue Holiday packing.
Let’s rewind to the Bucks’ title-winning season. That 2021 squad was built on grit, chemistry, and a defensive backbone anchored by Holiday, Middleton, and Giannis Antetokounmpo.
Since then, Milwaukee has remained all-in on building around Giannis - and understandably so. But despite that commitment, the Bucks have only made it past the first round of the playoffs once since hoisting the Larry O’Brien Trophy.
In 2023, the front office made a seismic move, trading Jrue Holiday in a package deal to acquire Damian Lillard. On paper, it looked like a power play - pairing Giannis with one of the league’s most dangerous offensive weapons.
But basketball isn’t played on paper, and the results never quite matched the expectations. The Bucks struggled to find rhythm and cohesion with Lillard in the mix, while Holiday landed in Boston and helped the Celtics capture another championship.
Middleton, who spent over a decade in Milwaukee, didn’t hide his disappointment when reflecting on the trade. Speaking candidly, he admitted how tough it was to watch Holiday - a close friend and key piece of their core - leave the team before they had a real shot to run it back healthy.
“I was close with his family,” Middleton said. “To lose that guy, without getting a real chance to get a healthy group back out there again and try to reclaim our throne, was a tough pill to swallow. I wish that we were able to have a couple more chances and get another crack at it.”
It’s the kind of sentiment that hits home for any fan who remembers how dominant that trio could be when firing on all cylinders. Injuries had taken their toll the season before the trade, and Middleton clearly felt the group never got a fair shot to defend their crown at full strength.
He also touched on the weight that comes with being the face of a franchise. Middleton acknowledged that Giannis, in his relentless pursuit of winning, put significant pressure on the Bucks’ front office - a pressure that led to bold decisions with unintended consequences.
“Giannis put a lot of pressure on the organization, but we all want to win,” Middleton said. “At times, we just don’t know what type of consequences that can have, good or bad.”
That’s the reality of building around a generational superstar. Every move is magnified.
Every decision carries risk. And when those moves don’t pan out, there’s a ripple effect - not just on the court, but in the locker room and in the long-term vision of the franchise.
Fast forward to this past offseason, and the Bucks made another major move - this time cutting ties with Lillard and bringing in Myles Turner. It was a bold pivot, and early returns suggest it’s working. Giannis is once again putting up MVP-caliber numbers, and the Bucks look more balanced, especially on the defensive end.
But there’s a caveat: waiving Lillard and stretching his contract has left Milwaukee with a significant financial burden. That cap hit could limit their flexibility in the seasons to come, potentially handcuffing the front office as they try to build a sustainable contender around Giannis.
For Middleton, now watching from afar, it’s clear that the Bucks’ journey has been shaped by a series of high-stakes gambles. Some paid off - like the 2021 title run.
Others, like the Lillard experiment, didn’t go as planned. And through it all, the emotional weight of what was lost - the chemistry, the trust, the chance to run it back with a healthy core - still lingers.
There’s no villain in this story. Just a team chasing greatness, a superstar demanding excellence, and a former cornerstone reflecting on the fine line between bold ambition and unintended fallout.