Grammy winner Zach Bryan struck a sharp fashion stance at Gillette Stadium on Friday night (October 2), wearing a black T-shirt that read “Free Palestine” during the first of two dates of his With Heaven On Tour in Foxborough, Massachusetts.
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Members of Bryan’s band were also spotted wearing matching shirts, according to TMZ, with fan images of the moment quickly circulating on social media. Bryan did not appear to address the jersey from the stage.
The choice of wardrobe – and location – is hard to dismiss as a coincidence. Gillette Stadium is owned by the Kraft Group, led by New England Patriots owner Robert Kraft, who weeks earlier played a central role in Macklemore’s exclusion from other U.S. dates of Ed Sheeran’s Loop tour due to the rapper’s pro-Palestinian statements on stage.
During his first sets at MetLife Stadium in East Rutherford, New Jersey, on September 4 and 5, Macklemore declared “Free Palestine” to the crowd and performed his 2024 protest song “Hind’s Hall.” On the second evening, he also spoke directly to Jewish supporters in attendance, saying his criticism of the Israeli government was not directed at them.
The Israeli-American Council launched a petition calling for his removal, and on September 14, tour promoter Messina Touring Group confirmed that Macklemore would no longer appear on other U.S. dates after several NFL stadium owners reportedly threatened to shut down shows if he remained on the bill.
Kraft confirmed his involvement in a statement the same day, saying he felt a responsibility to speak out when he believed a line had been crossed on anti-Semitism, while recognizing that Palestinian suffering was real.
Sheeran said in his own statement the following day that the withdrawal was the promoter’s decision, not his, and that he had spoken directly with Kraft while trying to find a solution.
The fallout was rapid. Fellow openers Finneas, Aaron Rowe and Lukas Graham left the tour in solidarity, as did Irish folk group Beoga, who played with Sheeran, while Macklemore responded with a lengthy Instagram post detailing the money, brand deals, festivals and private shows he says his advocacy has cost him.
He then pledged $1 million from his tour earnings to Palestinian aid organizations and announced a Free Palestine tour – a short European tour hitting Dublin, Paris and London from October 26-30 – which he said sold out immediately.
Sheeran ultimately never made it to Foxborough: his two dates at Gillette Stadium last weekend were canceled due to extreme weather – although the tour gave in to the demands of the venue’s owners.
Bryan rarely shied away from friction with powerful figures. In October 2025, a teaser for her song “Bad News” — which references ICE raids — drew public criticism from the Department of Homeland Security and the White House, with Homeland Security Secretary Kristi Noem saying at the time that she was disappointed by the clip. Bryan hit back at the time, arguing that the song spoke to both sides of the aisle and urging fans not to let social media narratives divide them. The track eventually appeared on his album With the sky on topreleased January 9, 2026.
Bryan is expected to return to Gillette Stadium for the second night of his Foxborough stand on Saturday (October 3) – and all eyes will be on whether the jersey makes another appearance and whether Kraft, who has yet to respond publicly, takes action. Representatives for Kraft did not immediately respond to requests for comment.
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