Zach Bryan wore a black “Free Palestine” T-shirt during his Friday, Oct. 2 concert at Gillette Stadium in Foxborough, Massachusetts, and then wore it again the second night, when his show broke the venue’s all-time attendance record. Members of his band were spotted in matching shirts, according to TMZ. Bryan did not address the shirts at either performance.
Probably not a good thing for any entertainer to go political, as that’s exactly how you lose fans. Did the fans at that show know he would be political? Because if so, they might not have bought a ticket.
The stadium is owned by Robert Kraft, who had previously given Ed Sheeran an ultimatum to drop rapper Macklemore or face a ban from major venues. Macklemore had been removed from the remaining U.S. dates of Sheeran’s Loop Tour after making pro-Palestinian remarks at MetLife Stadium in New Jersey on Sept. 4 and 5. For the record, Macklemore wasn’t booted just for saying “Free Palestine.” He showed up on stage in a keffiyeh and used imagery of a U.S. hundred-dollar bill intertwined with an Israeli flag in a jigsaw puzzle. That’s a bit more than a fashion statement.
Bryan’s two-night run at Gillette set a new record for the Kraft Group-owned venue, according to Billboard, which covered Bryan’s record-breaking Gillette Stadium shows. One social media user celebrated the numbers by calling Kraft and his “Israeli backers” a “HUGE miscalculation,” using the word “Crafty” to describe the Jewish billionaire. Classy stuff.
What makes this different from the Macklemore situation is who’s in the audience. Macklemore’s fans, to the extent they still existed before all this, skewed heavily toward the woke crowd. Bryan’s fanbase is overwhelmingly red-state, blue-collar Americans, the kind of people who built his career from the ground up. His three most recent albums have reached No. 1 or No. 2 on the Billboard 200, and his self-titled 2023 album has spent 162 weeks on the chart. He’s not some fringe act looking for attention. He’s at the top.
That makes the shirt a choice, not a reflex. An Australia/Israel Review of polling from 2014 to 2026 found that 68 percent of Gazans support armed terrorism against Israel. A November 2025 survey by the Palestinian Center for Policy and Survey Research found that more than half still supported the Oct. 7 attacks. Those are the politics Bryan decided to put on his chest in front of a stadium full of country music fans.
Bryan has also caught heat on other fronts. His most recent album included “Bad News,” a song that takes shots at immigration enforcement. And ex-girlfriend Brianna LaPaglia of Barstool Sports has publicly accused him of emotional abuse, claiming on her podcast that he offered her $12 million to sign a non-disclosure agreement. “The last year of my life has been the hardest year of my life dealing with the abuse from this dude,” she said. “I’m still scared right now because I’m scared of him. My brain’s rewired and I’m scared to make him mad.” Bryan has not publicly addressed those allegations in detail.
His label is probably thrilled. His fans, who showed up for heartfelt songs about working-class life, probably feel a little differently. Drop your thoughts in the comments or on social media, because something tells us people have opinions about this one.
