Philip Weiss sees himself as a kind of Theodor Herzl in reverse. Both men were working feature writers until a single comment led them to focus their attention on Israel, to the exclusion of everything else.

For Herzl, the father of political Zionism, it was when he heard chants of “Death to the Jews” on the streets of Paris. For Weiss, the founder of the anti-Zionist Web site Mondoweiss, it was when his brother mused aloud that the otherwise catastrophic Iraq War could be good for the Jews.

At that point, Weiss, who grew up in Baltimore, was known as a talented, versatile, and colorful magazine journalist, with bylines in all the best places. He snuck into Bohemian Grove, the ultra-secretive California retreat for wealthy conservatives, for Spy. He interviewed Jeffrey Epstein for New York magazine, and wrote about his taste in porn for Harper’s. He published two books: one nonfiction, American Taboo, investigating a murder in the Peace Corps, and one political satire, Cock-a-Doodle-Doo, based on his experiences as the boyfriend of Daniel Patrick Moynihan’s daughter, Maura.

“He was the person I called whenever we needed something that called for a capital-W ‘Writer,’” says Susan Morrison, Weiss’s editor at Spy and a longtime editor at The New Yorker. “He was just wonderfully game, and had an almost novelistic ability to be inside the emotional life of the people he was writing about.”

By the time the American bombs started falling on Baghdad, Weiss was writing mostly for The New York Observer, then edited by Peter Kaplan, a friend from college. “The Harvard Mafia, it really is true,” he says.

Kaplan proposed that Weiss start a blog, because it was the early 2000s and having a blog was like having a guitar in the 1960s. Kaplan wanted the blog to be about sex, or at least Weiss’s madcap exploits in the big city. “There was always a slightly priapic air to my work,” Weiss says. “I was a bad boy. I was provocative. Nick Lemann [the former dean of the Columbia Journalism School] once called me ‘the Dennis Rodman of journalism.’ I don’t like that sobriquet, but you can’t control your reputation.”

In 2006, not long after his brother’s fateful comment, Weiss went to Israel for the first time to cover the country’s war with Lebanon. When he returned, Kaplan called him into his office and said, “We are going to have a grown-up conversation.” Weiss was taken aback. “We had never had a grown-up conversation before,” he says.

Kaplan told him that the increasingly strident and political turn the blog had taken was unwelcome. “You’re an anti-Zionist,” Weiss recalls Kaplan, who died in 2013, telling him. “I am a Zionist. Jared [Kushner, who bought The New York Observer in 2006] is a Zionist. We don’t want it.”

“Do you understand there is no place for me?,” Weiss pleaded. “Jeffrey Goldberg just got some big promotion, and he is a Zionist. Ron Rosenbaum just got a big job, and he is a Zionist. I am anti-Zionist. There is no room for me!”

“You’re speaking politically,” Kaplan responded. “I want to speak to you personally. You are becoming a nut.”

Weiss took the blog to the Nation Institute, but he didn’t last long there either, because, he claims, his criticisms of “the Israel lobby” were too much for even the nonprofit arm of the left-wing magazine.

“Oh God, what is happening to my career?” he lamented to a friend.

Weiss now dismisses his previous output. “I was a trivial journalist,” he says.

After being cut loose from the Nation Institute, Weiss created Mondoweiss, which today has 10 full-time staffers, a stable of regular contributors, and an editor, Adam Horowitz, who actually runs it. Weiss says that in the past two years, the site has more than doubled its followers on X, to 160,200, and increased its followers on Instagram by a factor of five, to 176,000.

Two decades after being cast out from a profession that he’d spent the better part of a lifetime climbing the ranks of, Weiss finds himself at the center of what may be the most divisive issue of this election cycle, one that has traveled from the fringes of the left to the floor of the Democratic National Convention.

He snuck into Bohemian Grove, the ultra-secretive California retreat for wealthy conservatives, for Spy. He interviewed Jeffrey Epstein for New York magazine, and wrote about his taste in porn for Harper’s.

To pro-Palestinian activists who distrust mainstream coverage of the Israel-Hamas war, Mondoweiss “has given voice to a strain of opinion that in the past had few chances of being heard.” Others view it as “a hate site.”

Though Mondoweiss bears his name, Weiss is discovering that some of what is published there is too radical for even his tastes.

“To be honest, I feel a little done with the left,” Weiss says. “I think the left is correct, but I am just finding their company a little hard to take.”

Among his complaints: “The left’s analysis of Israel and Palestine is that it is settler colonialism. I find that too reductive.... That’s identity politics, and the mood of the left is identity politics, and I am not just an identitarian by nature.”

Weiss said he was recently at an anti-Zionist conference where the organizers screened an Israeli tourism advertisement featuring young women flirting with handsome Israeli soldiers. After showing it, the moderator asked people their reaction. Weiss said that it was nationalistic and militaristic, but that wasn’t what the moderator of the session was looking for. The right answer?

“It was so heteronormative!,” Weiss says with an exasperated laugh.

Weiss was at a public debate years ago where someone was inveighing against the creation of Israel, making comments that Weiss largely agreed with, when he heard an older person in the audience mutter softly, “Where were they supposed to go?”

“It is a really moving comment to me,” Weiss says. “It doesn’t justify Zionism in my view, but it has always been an answer to left-wing reductionism. There are refugees in this world, there are pitiable people in this world. I don’t want to be in that discussion, and the left doesn’t want to hear what I have to say.”

Nevertheless, “October 7 is a hugely clarifying event,” Weiss says. “It is a ‘Which side are you on?’ event. And here I should say some on the left are on the Hamas side. I am not. I don’t condone any of those atrocities, and my repeated condemnation of Hamas’s actions has upset some of my Palestinian friends who approve of what Hamas did.” Regardless, Israel’s actions since then have, he says, led inevitably to an upsurge in anti-Zionism, particularly among Democrats, in a way that was once unimaginable.

“Most Democrats say that a genocide is occurring in Gaza,” Weiss says. “Democratic leaders cannot say that. So the street says one thing, and the leaders say something else. There is great instability in the Democratic Party right now.”

Weiss points to the example of Algeria, where the nationalists drove out the French colonialists, putting up posters that said they had two choices: the suitcase or the coffin. “Even if you accept the colonial model of Israel-Palestine, that is not a good outcome,” he says. “I don’t think this ends well.”

Weiss believes “the only outcome that will end the violence” is a one-state solution—a post-Jewish Israel. “Zionism is clearly a problem,” he says, “and ought to be placed in the ‘course of extinction,’ as Lincoln said of slavery.”

“I think it ends in the United States,” he says. “Just as Algeria ended in France, de Gaulle had to change. Once de Gaulle changed, fucking Algerian oppression was cooked. The U.S. has to change on Israel, and that is what is happening now. And that is what I am very proud to be an agent of, a shift in the discourse.”

Soon after he fired him, Kaplan told Weiss that he was in danger of “being used.” “And he is right,” Weiss says. “I allowed myself to be used, and I am proud of the way I was used. It’s like Bill Withers sang, ‘Keep on using me, until you use me up.’ I lent myself to a cause.”

David Freedlander is a New York–based writer