Zach Bryan wore a “Free Palestine” T-shirt during a show at Gillette Stadium, weeks after Macklemore was dropped from Ed Sheeran’s US tour for pro-Palestine statements.

Bryan played the first of two dates at the Foxborough, Massachusetts venue last night (October 2) as part of his ongoing ‘With Heaven On Tour’ trek, and as he took to the stage, he and his band were wearing black shirts bearing the message.

The choice attracted particular attention because Gillette Stadium is owned by the Kraft Group, led by New England Patriots owner Robert Kraft, who was recently at the centre of the controversy surrounding Macklemore’s removal from Ed Sheeran’s ‘Loop’ tour.

Country singer Zach Bryan wore a “Free Palestine” shirt at his Gillette Stadium show in Massachusetts. pic.twitter.com/1sFUj1IF4c

— Pop Crave (@PopCrave) October 3, 2026

Zach Bryan rolled into Gillette Stadium, looked at a sold-out country crowd that drove hours to hear songs about trucks and bad decisions, and decided what they really needed was a foreign-policy seminar.

Him and the band walked out in “Free Palestine” shirts. Some of them also…

— D Mk (@wickedsmaahht) October 3, 2026

While supporting Sheeran at New Jersey’s MetLife Stadium in September, Macklemore delivered a speech expressing solidarity with Palestinians in Gaza and the occupied West Bank. He called for a “Free Palestine” and performed his protest track ‘Hind’s Hall’ alongside images from Gaza.

The Israeli-American Council and others subsequently called for Macklemore to be removed from the tour.

Kraft later said he considered Macklemore’s performances to be “deeply offensive and hurtful to the Jewish community”, and confirmed that the rapper would not be permitted to perform at Gillette Stadium.

Sheeran later said he was “not complicit” in Macklemore being dropped, saying he had spent days trying to find a solution. He said the ultimate decision was made by promoter Messina Touring after venues indicated that they would cancel shows if Macklemore remained on the bill.

FINNEAS, Lukas Graham, Aaron Rowe and Beoga subsequently withdrew from their support slots in solidarity with Macklemore, while members of Sheeran’s backing band also dropped out.

Macklemore then pledged his entire $1million earnings from Sheeran’s tour to six organisations supporting Palestinians, telling Kraft: “Whatever we disagree about, perhaps we can agree on this: Palestinian lives are worth protecting.” Kraft subsequently announced a $2million contribution to humanitarian aid in the region.

When Sheeran returned to the stage in Philadelphia on September 19, he apologised for “mistakes” in his handling of the controversy and revealed that the fallout had left him questioning whether he wanted “to be an artist at all”.

Macklemore has since announced his own ‘Free Palestine Tour’ of the UK and Europe, with proceeds going to organisations supporting Palestinians.

Earlier this week, he said all three dates had sold out, adding: “When those in power try to silence our calls for liberation, art will always be a form of resistance.”

Bryan is due to play a second sold-out night at Gillette Stadium tonight (October 3), before his ‘With Heaven On Tour’ concludes at Alabama’s Jordan-Hare Stadium on October 10.

The tour is in support of his latest album ‘With Heaven On Top’, and earlier this year included stadium shows across the UK and Europe.