Chris Hayes Mocks The Most ‘Ridiculous’ Detail About Trump’s Mar-A-Lago War Room

On Mar 4, 2026

Hey, at least he didn’t wear a propeller hat.

On Monday’s episode of MS NOW’s “All In,” host Chris Hayes trashed President Donald Trump’s eight-minute video — published in the wee hours of Saturday morning — in which he announced that the U.S. and Israel carried out an attack on Iran that killed Supreme Leader Ayatollah Ali Khamenei.

Hayes blasted several aspects of the video, as well as the attack’s execution and aftermath. But Hayes made it a point to call out one detail from Trump’s video that feels indicative of how messy everything about this attack looks: Trump’s “ridiculous” hat.

President Donald Trump wearing a baseball cap in January that looks very similar to the one he wore in his video Saturday.

“He launched a massive military undertaking, an unprovoked war of choice in the middle of the night, from behind some hastily hung curtains in his vacation home,” Hayes said. “Looking absolutely exhausted, I might add, wearing a ridiculous USA baseball cap.”

Trump looked pretty unserious during his serious announcement thanks to the cap. Not only was it way too casual for the occasion, but it was also too big for Trump’s head.

Comedian Jon Stewart mocked the vibe of the video during Monday’s episode of “The Daily Show” and said Trump’s hat looked like it was bought for him at an “airport souvenir store.”

“This is how we’re doing this?” a shocked Stewart said, pointing to an image of Trump in his big hat. “Two a.m., Mar-a-Lago basement? … This is what we’re wearing? Blazer, no tie, shirt unbuttoned?”

[embedded content]

Hayes also slammed Trump’s decision to launch the attack from his Palm Beach, Florida, golf club in a makeshift war room, calling it an “operational security nightmare.”

“One might wonder, can any Mar-a-Lago guests just swing by and poke their head in to take a look at the big poster showing the location of all of our military personnel and the targets we’re going for?” Hayes said. “Is it cool to wear an Apple Watch and bring your iPhone into the supposedly secure facility near all the dancing? Those are real questions.”

Hayes also made it a point to highlight how nonchalant Trump has seemed about the loss of service members’ lives amid the attack, as well as his equally unbothered attitude about how there will “likely be more” service members who will die in the conflict.

“Trump’s tone in talking about the dead U.S. service members, the ones who lost their lives and the ones who may lose their lives in the future, as just part of what happens in war, is representative of the shocking glibness with which Trump has handled this entire war,” Hayes said.