Country singer Zach Bryan, who wore a ‘Free Palestine’ shirt while performing at Robert Kraft’s Gillette Stadium, has a long history of making controversial political statements.Navy veteran Bryan, 30, sported the black shirt in support of Palestine onstage as he played at the sold-out arena in Foxborough, Massachusetts, on Friday night.His choice of shirt came just weeks after businessman Kraft, 85, effectively banned Macklemore from playing at the stadium over pro-Palestine comments he made while on Ed Sheeran’s tour.Friday’s show was not the first time that Bryan, a Grammy Award winner, has voiced his political beliefs. He is scheduled to play at Gillette Stadium for the second straight night on Saturday.Bryan previously described himself as a ‘total libertarian’ in a New York Times article published September 2022.In that same interview, Bryan also noted that he had attempted to stop chants targeting former president Joe Biden at his shows.’I told people if I heard it, I would stop it immediately,’ Bryan told the outlet.He added: ‘Don’t come to my shows and start it. But they do it anyway.’ Country singer Zach Bryan, 30, wore a black shirt that said ‘Free Palestine’ as he played at Robert Kraft’s Gillette Stadium on Friday night Bryan, who previously called himself a ‘total libertarian,’ wore the shirt weeks after Kraft banned Macklemore from playing at the stadium over pro-Palestine comments The country singer posed with Trump for a picture in February 2025 while at the Super Bowl in New OrleansIn October 2025, Bryan took heat from the Trump administration for his song ‘Bad News,’ in which he appeared to criticize Immigration and Customs Enforcement (ICE) agents.’ICE is gonna come bust down your door,’ he said in that song. ‘Try to build a house no one builds no more.’Bryan also sang about ‘the fading of the red, white and blue’ as part of the track.The White House responded to Bryan’s lyrics and perceived political messaging by mentioning his own past songs.’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 urged Bryan to ‘Stick to Pink Skies, dude,’ in reference to his 2024 song.Bryan responded to the firestorm that his song caused by saying the track was ‘about all of us coming out of this divided space.”Left wing or right wing we’re all one bird and American,’ he posted on Instagram. ‘To be clear I’m on neither of these radical sides.’He added: ‘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 nightDuring 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.’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 commentsBryan 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 careerGillette 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.The Daily Mail 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.