Country music star Zach Bryan sparked attention at Robert Kraft’s Gillette Stadium by performing in a “Free Palestine” shirt—a move that adds to his history of outspoken and sometimes controversial political comments.
The 30-year-old Navy veteran wore the black shirt during his sold-out concert at the Foxborough, Massachusetts, stadium on Friday night, signaling his support for Palestine from the stage.
Bryan’s decision came only weeks after businessman Robert Kraft, 85, effectively barred Macklemore from performing at the venue following pro-Palestinian remarks the rapper made during Ed Sheeran’s tour.
The Grammy-winning singer has previously used his platform to discuss politics. Bryan is due back at Gillette Stadium on Saturday for the second of two consecutive performances.
In a New York Times interview published in September 2022, Bryan described himself as a “total libertarian.”
During that conversation, he said he had also tried to prevent audiences at his concerts from launching chants aimed at then-President Joe Biden.
“I told people if I heard it, I would stop it immediately,” Bryan told the newspaper.
“Don’t come to my shows and start it. But they do it anyway,” he added.
Country singer Zach Bryan, 30, performed at Robert Kraft’s Gillette Stadium on Friday night wearing a black “Free Palestine” shirt
Bryan, who once described himself as a “total libertarian,” wore the shirt weeks after Kraft effectively barred Macklemore from performing at the stadium following pro-Palestinian comments
The country singer posed for a photo with Trump in February 2025 while attending the Super Bowl in New Orleans
Bryan also faced criticism from the Trump administration in October 2025 over his song “Bad News,” which appeared to take aim at Immigration and Customs Enforcement agents.
“ICE is gonna come bust down your door,” Bryan sings in the track. “Try to build a house no one builds no more.”
The song also references “the fading of the red, white and blue.”
The White House responded to the lyrics and their perceived political message by drawing on titles and themes from Bryan’s own music.
“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!” a White House spokesperson told Newsweek at the time.
The Department of Homeland Security also addressed the singer directly, telling him to “Stick to Pink Skies, dude,” a reference to his 2024 song.
As the backlash grew, Bryan said “Bad News” was intended to reflect the country’s struggle to move beyond political division.
“Left wing or right wing we’re all one bird and American,” he wrote on Instagram. “To be clear I’m on neither of these radical sides.”
He continued: “Just know I’m trying my best too and we all say things that are misconstrued sometimes.”
Bryan said in September 2022 that he had previously tried to ‘immediately’ stop negative chants aimed at Joe Biden at his shows
Kraft, 85, owns the arena in Foxborough, Massachusetts, where Bryan is scheduled to play again on Saturday night
During the 2024 presidential election, Bryan addressed whether he supported Biden or Donald Trump in a video reacting to the GOP candidate having survived an assassination attempt at a Pennsylvania campaign rally that July.
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‘I don’t support Trump or Biden,’ Bryan said in the Instagram video. ‘But the man got shot in the ear, head, whatever you guys want to call it.’
‘And then, fist bump in the air!’ the singer continued. ‘That is sick, dude!’
Bryan was pictured with Trump in February 2025 while attending the Super Bowl in New Orleans.
The country singer captioned the picture of him and Trump with comedian Shane Gillis, ‘the actual smallest man.’
‘To be clear: I obviously was referring to me being the smallest man in the photo and not the President of the United States,’ he later explained, according to WhiskeyRiff.
Bryan has said that he is a libertarian, but his previous political comments have also indicated support for working class people and policies.
In 2022, he said that ‘working class people should still be able to afford tickets to shows,’ The Associated Press reported.
Bryan previously said that he did not support Biden or Donald Trump during the 2024 presidential election
Bryan wore the ‘Free Palestine’ shirt after Macklemore was removed from Ed Sheeran’s tour after making pro-Palestine comments
Bryan added that songwriters attempting to make so-called ‘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, his first of the kind, called All My Homies Hate Ticketmaster in late 2022 over his frustration with the company’s ticket prices.
However, he effectively reversed course the following year and said it was ‘hard to realize one guy can’t change the whole system.’
Prior to becoming a singer, Bryan served in the US Navy for eight years after enlisting at 17.
He was an aviation ordnanceman who completed tours in Djibouti and Bahrain before being honorably discharged in 2021 after signing a record deal with Warner Records.
The singer said he had served ‘the best country in the whole damn world’ and ‘the world’s greatest Navy.’
Bryan, who was born in Japan because his parents were stationed overseas due to a Navy deployment, was continuing a family tradition.
Bryan served in the US Navy for eight years and completed tours in Djibouti and Bahrain before being honorably discharged in 2021 to pursue his music career
Gillette Stadium is yet to comment on Bryan’s ‘Free Palestine’ shirt that he wore onstage Friday.
The shirt also sported the words ‘appeal to heaven,’ which is a phrase that goes back to the Revolutionary War and was previously on the maritime flag of Massachusetts.
Meanwhile, Bryan’s bandmates also wore clothes related to Palestine during the performance.
Our News Outlet has reached out to the Kraft Group, which owns Gillette Stadium, for comment.
As of Saturday afternoon, the management email listed by Bryan on his website appeared to not be working.
