Skip to main content

Damian Lillard trade just keeps getting worse for the Bucks

The trade is haunting the Bucks years down the line.
Milwaukee Bucks guard Damian Lillard (0) reacts after being injured against the Atlanta Hawks during the first half at State Farm Arena on March 4, 2025.
Milwaukee Bucks guard Damian Lillard (0) reacts after being injured against the Atlanta Hawks during the first half at State Farm Arena on March 4, 2025. | Dale Zanine-Imagn Images

The Damian Lillard trade was a disaster from the start, but somehow it keeps finding new ways to hurt Milwaukee. Now we're learning Giannis himself told Jrue Holiday how much they screwed up by letting him go.

According to Ramona Shelburne's ESPN report, sources told ESPN that "Antetokounmpo confided to Holiday how much he and the Bucks missed Holiday's defense and leadership." And that's damning.

Giannis just showed what he really thinks of the Bucks

Holiday's defense and leadership were exactly what made the 2021 championship work. He could guard anyone, made everyone else's defensive job easier, and knew how to win because he'd done it before. Those aren't things you find on the buyout market or through mid-season trades. That's championship DNA you build around.

Instead, Milwaukee traded it all away for Damian Lillard, who couldn't defend anyone and never figured out how to coexist with Giannis. Then they cut Lillard for Myles Turner, who's getting outplayed by Jericho Sims nightly.

So, beyond the basketball stuff, the confession to Holiday also ultimately reveals something about Giannis's mindset right now. The fact that he's actively communicating with former teammates about how much better things used to be betrays someone who's already mentally checked out. And at this point, it's hard to imagine anyone with that mindset deciding to stick around for another season.

Just imagine being Jon Horst and reading this report. Your franchise player just told the guy you traded away that he misses him. It wasn't explicit, but he essentially communicated, too, that the team's worse without him. That's a public indictment of your biggest roster decision, delivered directly by the person you were trying to help.

Holiday's probably got mixed feelings about this, too. On one hand, validation that Milwaukee realizes its mistake. On the other hand, he's in Portland now, watching his former team fall apart while knowing he could've been the piece that kept it together.

Antetokounmpo's comments speak volumes about current Bucks

The leadership comment is particularly damning because that's not something you can replace through trades or free agency. Holiday brought championship experience, defensive intensity, and the kind of veteran presence that keeps locker rooms together during adversity. Milwaukee has none of that now, and it shows in how quickly everything's falling apart.

By reaching out to a former teammate, Giannis also publicly bashes where the team is currently. Current point guards like Ryan Rollins and Kevin Porter Jr. should be feeling some type of way about this right about now, especially since the former has even been compared to Holiday at certain points earlier this season.

The Damian Lillard trade will haunt the Bucks forever. Not just because it failed, but because it failed so spectacularly that their own franchise player is apologizing to the guy they traded away. That should be an embarrassment to the Bucks organization as a whole.

Milwaukee had a championship formula with Antetokounmpo and Holiday. They blew it up chasing a bigger name that never fit. Now they're paying the price while Holiday in Portland is proving he still has plenty left to give.

And Giannis, the one guy they made this whole mess for in the first place, is telling Holiday how much he misses him. That's not just the trade getting worse. That's the trade becoming a punchline that Milwaukee will never live down.

You make that move nine times out of ten, but this might be the one timeline where it just didn't work out.

Loading recommendations... Please wait while we load personalized content recommendations