Country singer Zach Bryan, a U.S. Navy veteran, wore a 'Free Palestine' shirt while performing at Robert Kraft's Gillette Stadium on Friday night, drawing attention to his history of controversial political statements. The 30-year-old artist sported the black shirt at the sold-out arena in Foxborough, Massachusetts.
Bryan's shirt choice comes weeks after businessman Robert Kraft reportedly banned Macklemore from performing at the same venue due to pro-Palestine remarks made during an Ed Sheeran tour stop. Bryan is scheduled to perform a second consecutive night at Gillette Stadium on Saturday.
This is not the first time the Grammy winner has voiced political opinions. In a September 2022 interview with The New York Times, Bryan described himself as a "total libertarian." During the same interview, he stated that he had attempted to prevent anti-Joe Biden chants at his concerts, telling the outlet, "I told people if I heard it, I would stop it immediately. Don't come to my shows and start it. But they do it anyway."
In October 2025, Bryan faced criticism from the Trump administration for his song "Bad News," which appeared to criticize Immigration and Customs Enforcement (ICE) agents. Lyrics included, "ICE is gonna come bust down your door. Try to build a house no one builds no more," and mentioned "the fading of the red, white and blue."
A White House spokesperson responded at the time, stating, "While Zach Bryan wants to Open The Gates to criminal illegal aliens and has Condemned heroic ICE officers, Something in the Orange tells me a majority of Americans disagree with him and support President Trump's great American Revival. Godspeed, Zach!" The Department of Homeland Security also commented, urging Bryan to "Stick to Pink Skies, dude," referencing one of his songs.
In response to the controversy surrounding "Bad News," Bryan posted on Instagram that the track was "about all of us coming out of this divided space." He added, "Left wing or right wing we're all one bird and American. To be clear I'm on neither of these radical sides." He also acknowledged that "we all say things that are misconstrued sometimes."
During the 2024 presidential election cycle, Bryan addressed his political leanings in a video reacting to an assassination attempt on Donald Trump. "I don't support Trump or Biden," Bryan stated. "But the man got shot in the ear, head, whatever you guys want to call it. And then, fist bump in the air! That is sick, dude!"
Bryan was photographed with then-candidate Donald Trump and comedian Shane Gillis at the Super Bowl in New Orleans in February 2025. Bryan captioned the photo with Gillis, "the actual smallest man," later clarifying he was referring to himself in the image.
Beyond his libertarian identification, Bryan's past comments have also suggested a concern for working-class individuals. In 2022, he told The Associated Press that "working class people should still be able to afford tickets to shows." He expressed that songwriters creating "relatable music for the working class man or woman" should "pride themself on fighting who listen to the words they're singing." He released a live album titled "All My Homies Hate Ticketmaster" in late 2022, citing frustration with the company's ticket pricing, though he later noted that "it was hard to realize one guy can't change the whole system."
Bryan served in the U.S. Navy for eight years, enlisting at age 17. He completed tours in Djibouti and Bahrain as an aviation ordnanceman before being honorably discharged in 2021 to pursue his music career. He previously stated he served "the best country in the whole damn world" and "the world's greatest Navy."
Gillette Stadium has not yet commented on Bryan's 'Free Palestine' shirt. The shirt also displayed the phrase 'appeal to heaven,' a historical reference dating back to the Revolutionary War and previously featured on the maritime flag of Massachusetts. Bryan's bandmates also wore clothing related to Palestine during the performance. The Kraft Group, which owns Gillette Stadium, has been contacted for comment. As of Saturday afternoon, the management email listed on Bryan's website appeared to be non-functional.