Zach Bryan wears "Free Palestine" shirt in major dig at Robert Kraft after Macklemore drama

Foxborough, Massachusetts - Country singer Zach Bryan sported a "Free Palestine" shirt during his show at Gillette Stadium on Friday, just a few weeks after the stadium's owner, Robert Kraft, refused to allow rapper Macklemore on stage over pro-Palestinian comments.

Zach Bryan performs at the T-Mobile Mane Stage during the 2025 Stagecoach Festival on April 25 in Indio, California. The country singer wore a "Free Palestine" shirt as he performed at Gillette Stadium on Friday.
Zach Bryan performs at the T-Mobile Mane Stage during the 2025 Stagecoach Festival on April 25 in Indio, California. The country singer wore a "Free Palestine" shirt as he performed at Gillette Stadium on Friday.  © Frazer Harrison / GETTY IMAGES NORTH AMERICA / Getty Images via AFP

Bryan played the first of two shows at Gillette Stadium in Foxborough, Massachusetts, on Friday to a sold-out crowd.

As he hit the stage, he stepped out in a black tank top that read "Free Palestine," alongside a pine tree and the words "An Appeal to Heaven" underneath, per social media footage.

Several of Bryan's band members also wore clothing displaying support for the people of Palestine.

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The venue at which the 30-year-old chose to wear the shirt has raised some eyebrows, as stadium owner Robert Kraft was the one who spearheaded a push to have Macklemore removed from Ed Sheeran's tour after the rapper declared "Free Palestine" on stage at an earlier stop.

According to Macklemore, Kraft warned Sheeran that he would not be allowed to perform at Gillette if the Thrift Shop artist was still an opening act, and enlisted other stadium owners to back him up.

Macklemore's subsequent removal from the tour sparked outrage – so much so that Sheeran's other supporting acts and backup band quit in solidarity with both Macklemore and the Palestinian people.

Sheeran's performances at Gillette on September 25 and 26 were ultimately canceled due to severe weather.

In the aftermath, Macklemore has announced his own Free Palestine Tour, hitting Dublin, Paris, and London later this month.

"It's 2026. Being apolitical during a genocide doesn't work anymore," he wrote in his announcement, throwing some shade at Sheeran and his self-proclaimed refusal to take definitive stances on political subjects.

Zach Bryan is set to return to the Gillette Stadium stage on Saturday night.

Cover photo: Frazer Harrison / GETTY IMAGES NORTH AMERICA / Getty Images via AFP

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