Grammy winner Zach Bryan made a bold fashion statement at Gillette Stadium on Friday night (Oct. 2), wearing a black T-shirt that read “Free Palestine” during the first of two dates on his With Heaven On Tour at the Foxborough, Mass., venue.

Members of Bryan’s band were also seen in matching shirts, according to TMZ, with fan footage of the moment quickly circulating on social media. Bryan did not appear to address the shirt from the stage.

The choice of wardrobe — and venue — seems unlikely to be coincidental. Gillette Stadium is owned by the Kraft Group, led by New England Patriots owner Robert Kraft, who weeks earlier played a central role in removing Macklemore from the remaining U.S. dates of Ed Sheeran’s Loop Tour due to the rapper’s pro-Palestinian statements onstage.

During his opening sets at MetLife Stadium in East Rutherford, N.J., on Sept. 4 and 5, Macklemore declared “Free Palestine” to the crowd and performed his 2024 protest song “Hind’s Hall.” On the second night, he also spoke directly to Jewish fans in attendance, clarifying that his criticism of the Israeli government was not directed at them.

The Israeli-American Council launched a petition calling for his removal, and on Sept. 14 tour promoter Messina Touring Group confirmed Macklemore would no longer appear on the remaining U.S. dates after multiple NFL stadium owners reportedly threatened to withdraw shows if he stayed on the bill.

Kraft confirmed his involvement in a statement that same day, expressing that he felt a responsibility to speak up when he believed antisemitism had crossed a line, while acknowledging that Palestinian suffering is real.

Sheeran stated in his own statement the following day that the removal was the promoter’s decision, not his, and that he had spoken directly with Kraft while trying to find a resolution.

The fallout was swift. Fellow openers Finneas, Aaron Rowe and Lukas Graham exited the tour in solidarity, as did Irish folk band Beoga, who had been performing with Sheeran, while Macklemore responded with a lengthy Instagram post detailing the financial impact his advocacy has had on him.

He later pledged $1 million from his touring earnings to Palestinian aid organizations and announced a Free Palestine Tour — a short European run hitting Dublin, Paris and London from Oct. 26 to 30 — which he has since reported sold out immediately.

Sheeran ultimately did not perform in Foxborough: his two Gillette Stadium dates last weekend were canceled due to severe weather conditions — despite the tour having bowed to the venue owners’ demands.

Bryan has rarely shied away from conflict with powerful figures. In October 2025, a teaser of his 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 expressing disappointment regarding the clip. Bryan pushed back at that time, arguing that the song addressed both sides of the aisle and urging fans not to let social media narratives divide them. The track ultimately appeared on his album With Heaven on Top, released Jan. 9, 2026.

Bryan is scheduled to return to Gillette Stadium for the second night of his Foxborough stand on Saturday (Oct. 3) — and all eyes will be on whether he wears the shirt again, and whether Kraft, who has yet to publicly respond, will take any action. Representatives for Kraft did not immediately respond to requests for comment.