Kraft’s philanthropy extends to a wide variety of causes, including universities and hospitals. In 2020, during the pandemic, he donated 1.2 million N95 masks to medical workers in New York and Massachusetts. His primary largesse, however, has gone to Jewish and Israeli organizations. He donated $10 million to renovate Boston’s Combined Jewish Philanthropies headquarters and $11.5 million to construct a Columbia/Barnard Hillel building. In 1989, he launched the Passport to Israel Fund to help Boston-area teenagers visit Israel, built several football fields in Israel, and brought famous athletes to the country. In 2023, Kraft founded the “Stand Up to Jewish Hate” campaign to raise awareness about antisemitism, including a 30-second $7 million commercial during the 2024 Super Bowl. That year, Kraft, who had donated at least $18 million to Columbia, suspended his contributions during the pro-Palestine campus protests. Since 2021, Kraft and the Kraft Group have contributed over $3 million to the American Israel Public Affairs Committee and its affiliated super PACs.

In 2019, he was given the annual $1 million Genesis Prize for his charitable giving. At the award ceremony, Prime Minister Benjamin Netanyahu said, “Israel does not have a more loyal friend than Robert Kraft.”

Kraft has stirred several controversies. In 2019, he was charged with soliciting prostitution and hired one of Jeffrey Epstein’s attorneys to his legal team. (The charges were dropped in 2020.) He’s faced scrutiny over the use of his team’s planes for three deportation flights to Honduras in 2022.

Artists often cancel shows, typically for health reasons, but occasionally for political ones, like those who refused to perform at the Kennedy Center after Trump’s takeover. But in this case it was the venues’ billionaire owners who did the canceling.

Under those circumstances, it isn’t clear that the venues would have sued Sheeran if he had stood up for Macklemore. Would Kraft sue Sheeran—who played for free at Kraft’s 2022 wedding as thanks for the invitation to perform at Gillette Stadium early in his career—to recover money from the concert whose cancellation he, not Sheeran, initiated? Would other venue owners do so?

If Sheeran disagreed with Macklemore’s views, he could have made a statement about free speech and followed the example of the Jewish pop star Pink, who reposted an anti-Macklemore meme and then issued her own statement explaining why she disagreed with the rapper’s comments.

Sheeran said he was “not complicit” in what Kraft did and that not speaking publicly about the Middle East was not proof that he “didn’t care.”

“I am appalled by the conflicts between Israel and Palestine,” he wrote. “The suffering and pain caused on both sides is a human tragedy.”

He opposed Israel’s actions in Gaza, he said, but did not want to use his concerts or fame to make a political statement because he considers them a “place of safety and sanctuary.” “There is a reason I do not use my professional platform for politics,” he said. “My audience includes young people, often children, of all backgrounds.”

But Sheeran has made political statements before. He backed leftist Labour Party leader Jeremy Corbyn. He opposed Brexit. He headlined a benefit concert for Ukraine, recorded a music video with the Ukrainian band Antytila, and recorded a protest song with U2 about Russia’s Ukraine War.

These stances are contentious, but not as controversial as Israel and Palestine, especially among the demographic who attend Sheeran’s concerts, for whom there’s no room for neutrality.

Kraft’s views on Israel are also controversial, but he has the power to decide that Macklemore’s views are too objectionable to be heard on Gillette Stadium’s stage. In objecting to Macklemore’s “free Palestine” comment, Kraft also mentioned the artist’s “broader history of antisemitic rhetoric and imagery.”

Kraft was referring to a 2014 incident when Macklemore took the stage in Seattle wearing a bushy black beard, dark wig, and large prosthetic hook nose. Jewish groups said the costume reflected anti-Jewish stereotypes. Actor Seth Rogen tweeted, “If I told someone to put together an antisemitic Jew costume, they’d have that exact shopping list.”

Macklemore defended the outfit as a random disguise meant to help him walk through the crowd undetected. “A Jewish stereotype never crossed my mind,” he wrote on his website, while acknowledging how “the costume could, within a context of stereotyping, be ascribed to a Jewish caricature. I am here to say it was absolutely not my intention.”

In a society that claims to promote free speech, what crosses the line from controversial to unacceptable? Who gets to define where the line begins and ends?

In June, Tampa’s Raymond James Stadium, one of the venues on Sheeran’s tour, hosted rapper Ye (formerly known as Kanye West), whose vulgar antisemitic rants are well-known. Jewish and political leaders urged the Tampa Sports Authority to cancel his two concerts, but it cited contractual obligations and free speech protections as reasons to let Ye perform.

In 2003, the country band Dixie Chicks (who later dropped “Dixie” from their name) publicly criticized President George W. Bush’s imminent invasion of Iraq, saying they were ashamed that he was from their home state of Texas. The backlash was fast and furious. Radio stations refused to play their music. They received death threats, and were criticized by other country musicians. Sales of their music and concert tickets declined. They lost corporate sponsorships.

If any performer takes the stage wearing blackface makeup, it would likely generate considerable media attention and lead to cancellations of performances. The career of Michael Richards, who played Kramer on Seinfeld, never recovered from his racist slur against a heckler during a 2006 comedy act.

In 2018, ABC canceled Roseanne Barr’s sitcom after she compared Obama adviser Valerie Jarrett, who is Black, to an ape. In 2021, actress Gina Carano was fired from the TV show The Mandalorian after she shared a social media post that compared being a Republican nowadays to being Jewish during the Holocaust.

Did Macklemore’s comments cross some line? Kraft thinks so, but to a growing number of Americans—especially those under 40—criticism of Israel for its war in Gaza, occupation of Arab areas, and mistreatment of Palestinians is hardly controversial. Even the use of the word “genocide” is no longer off-limits except to Israel’s most rabid defenders. A July 2026 Economist/YouGov poll reported that 43 percent of Americans believe Israel is committing genocide against Palestinian civilians. A 2025 Washington Post poll found that 39 percent of American Jews agreed.

Given the current controversy, ticket sales for Sheeran’s concerts will likely be diminished. As will Sheeran’s reputation.

Could he have found alternative venues in the same cities and kept Macklemore in the show?

Will Sheeran’s fans and critics be mollified by his September 16 pledge to donate $2 million to Palestinian relief efforts? He persuaded Kraft to match his contribution. Macklemore said he would contribute $1 million.

Much depends on which groups get the money. In addition to humanitarian aid, they could donate to organizations working for a sustainable peace between Jews and Palestinians, such as Standing Together, and human rights groups that support Palestinians, such as the Association for Civil Rights in Israel, Adalah (the Legal Center for Arab Minority Rights in Israel), B’Tselem, Breaking the Silence, Yesh Din, and Human Rights Watch, and Doctors Without Borders (which Israel has banned from Gaza).

Sheeran’s own foundation primarily provides grants to youth-oriented music programs in the UK. Now, whatever his good his charitable works do, his name is sullied. Some fans and publications are calling him a “coward.” Whether he can recover will be determined by what he does to limit the reputational damage, maintain the loyalty of his millions of fans, and walk the tightrope over art, politics, and the Middle East.