Shabbos Kestenbaum is an Orthodox Jew, a registered Democrat, a Trump supporter, and a lightning rod on both sides of the political divide, he’s emerged as one of the most vocal pro-Israel advocates in the West. With his signature blend of unfiltered commentary, unapologetic Zionism, and willingness to spar with anyone from CNN anchors to campus radicals, he’s not here to make friends. He’s here to make a point.
"Certainly of my lifetime," he said without hesitation when asked if Israel is facing its worst global image crisis to date. "That’s unquestionable. And it presents a problem. It also presents an opportunity."
In his view, American Jewry—especially its younger generation—has undergone a jarring awakening. “Young American Jews, we never experienced Israel as an existential issue,” he explained. “It’s where our grandparents live. It’s where we go for Passover vacation. We’ll go to Yeshiva there. Some will even make aliyah. But we took it for granted. And October 7 made Israel in our minds a question mark—where its legitimacy, its survival, and yes, its existence was now in question.”
He calls them the “October 7 generation,” a cohort forced into political clarity. “All public opinion polling, done by the American Jewish Committee, by the Anti-Defamation League, clearly shows that young American Jews support Israel by and large,” he noted. “At the same time, antisemitism and anti-Israel sentiments are widespread. To be called ‘Zionist’ on a college campus—whether it’s Harvard, Columbia, or a state school—would be the equivalent of a gay student in the ’90s being called, you know, the F word. It’s a pejorative. It’s dirty.”
The problem, he argues, is not just the hate—but Israel’s catastrophic failure to counter it. “Israel has done itself a tremendous disservice by not producing enough resources to fight in the war of ideas. I wouldn’t say we’re losing. I would say we actually lost.”
And yet, Kestenbaum remains a pragmatist. The war may be brutal, but the battle for hearts and minds isn’t over. “It’s sort of yes and no,” he said when asked if public opinion is irretrievable. “I posted on my X about a week or two ago that Israel is the startup nation. They have some of the most creative minds—not just in the Middle East but in the world—yet they have really shitty PR.”
The fixes, he believes, aren’t complicated. “Israeli ministers with limited English skills, for example, should not be going on combative media at all. Sara Netanyahu should not be dictating internal policy. And it was wrong to have fired Elon Levy. Rehire him. Create an Israel war room of young Israelis, young Americans who are paid very well, and their entire job is to debunk the bizarre conspiracies and the libels that spread like wildfire on social media.”
But it’s not just about tech-savvy war rooms. It’s about showing up, especially when it’s uncomfortable. “The Prime Minister won’t hold a press conference. He won’t answer any questions. He won’t make himself visible to media. And then just relies on American Jews to support it? Well, we don’t even know what we’re supporting anymore.”
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Kestenbaum isn’t shy about calling for bold moves, even controversial ones. “Piers Morgan did an interview with Bibi 3 or 4 years ago, and he liked it. When I was on Piers yesterday, I even said, ‘Piers, I agree. You should be allowed into Gaza. You should meet Palestinians. You should meet the Druze. You should meet injured soldiers. You should meet hostage families. You should go to the Gaza Humanitarian Foundation and watch the aid distribution. And yeah, you should sit down with the Prime Minister.’”
The cost of Israel’s media opacity, he warned, is too high. “The Prime Minister does not make himself available to Western audiences that aren’t Fox News. And I’m sorry, that may have worked 10, 20 years ago. It just doesn’t work anymore.”
Jewish activist Shabbos Kestenbaum in an interview
(צילום: אסף חן)
He’s also attuned to a shifting tide within American conservatism. “We cannot take conservative thought leaders in the Republican Party for granted,” he said. “Young conservatives, even young evangelicals, are not nearly as pro-Israel as their parents and grandparents. On the contrary, many of them have very skeptical views of Israel.”
As for backlash? He wears it like armor. “The backlash is pretty tremendous. I get death threats weekly from the far left and the far right. I’m very bipartisan—because both sides want to kill me,” he quipped. “The Democratic Party wants nothing to do with me because I supported Trump. But the Republicans are very skeptical about me because I’m still a registered Democrat.”
His resilience is rooted in something deeper than politics. “My brother was born on Yom Ha’atzmaut (Israeli independence day). His name is Independence,” he said. “My mom would drive us to school every morning and play Naomi Shemer in the car. Being a Jew intrinsically means an attachment and a connection to the land of Israel.”
Young conservatives, even young evangelicals, are not nearly as pro-Israel as their parents and grandparents
And that connection isn’t symbolic—it’s devotional. “I pray three times a day. And when I pray, I mention the return to Zion dozens and dozens of times. Just two days ago was Tisha B’Av, where we sat on the floor and wept about our exile. Being Jewish just intrinsically, without even thinking about it, is an attachment to the land of Israel.”
What he offers isn’t blind defense—it’s full-throated admiration. “I don’t defend Israel. I laud and applaud them,” he said. “What they have done in a hostile, regressive region—as it pertains to multiculturalism, ethnic diversity, democracy, LGBTQ+ rights, women’s rights—that is a state that I don’t defend. I applaud and put on a pedestal.”
Even with all the threats and media pile-ons, he isn’t stepping back. “It’s almost a badge of honor. If the people who burn American flags don’t like me, I’m clearly doing the right thing.”