Simon Mann, who died this week at 72, lived the kind of life that makes a Jason Bourne movie feel pedestrian. He was a decorated SAS officer, the son of an England cricket captain, Old Etonian, mercenary, blood-diamond dealer, oil opportunist, failed coup plotter, and—as I discovered one afternoon while reading Rabbi Mordechai Elefant’s unpublished memoirs—a prospective convert to Orthodox Judaism under the tutelage of my esteemed Rosh Yeshiva.
Yes, you read that right. Somewhere between planning the overthrow of West African dictators and shooting the breeze over claret at White’s, Simon Mann was—at least for a brief, surreal moment—on the path to becoming a fully-fledged Jew.
Rabbi Mordechai Elefant (1930-2009) was a brilliant, larger-than-life Torah giant who built a yeshiva empire in Israel, hobnobbed with Mossad agents and world leaders, and never met a boundary he wasn’t willing to cross. His connection to Simon Mann began, as many of Rabbi Elefant’s most bizarre escapades did, with a phone call from his friend David Kimche, the legendary Mossad operative.
“There’s a British officer here with me,” Kimche told him. “He wants to marry a Jewish girl. Jewish him up.” Without missing a beat, Rabbi Elefant agreed.
The guy who turned up at Rav Elefant’s sukkah in Bet Safafa shortly afterward was pure colonial swagger: charming, well-spoken, and radiating James Bond-style bravado. Mann had charisma in spades, but not much in the way of Jewish observance – nor, frankly, any interest.
Rabbi Elefant didn’t mince his words. “You can’t convert just to marry her,” he told him flatly. Still, he arranged a tutor. “No promises,” he said. But clearly something about this soldier of fortune intrigued him.
What followed reads like a fever dream, the script of an exaggerated Hollywood movie.
Rabbi Pini Dunner.
Mann brought Rabbi Elefant cigars from Angola. Flew him around Africa on private planes. Introduced him to Tony Buckingham, his alleged MI6 handler (Mann later denied this to me in an email — “I know why he thought we were MI6, but we weren’t”). He briefed the rabbi on UNITA’s operations and diamond logistics, and even tried to loop him into business deals.
Rabbi Elefant — who had his own long and tangled history in Angola — knew the Angolan strongman Jonas Savimbi (1934–2002) well and was entirely unfazed. “I reported some of what Mann told me back to Savimbi,” he wrote. “He couldn’t figure out how I knew. I was the intelligence source.” An American-born, Jerusalem-based Orthodox rabbinic scholar dropping intel to an African warlord. You really can’t make this stuff up.
It gets better. Rabbi Elefant recalled that Mann warned him not to mention his name in certain parts of Africa. “Savimbi will kill you,” Mann said. “I’m serious.” Unbothered, Rav Elefant flew in anyway, dealt with warlords, and returned with diamonds—and stories that could make your head spin.
Rabbi Elefant died in 2009, after years of health decline, legal entanglements, and institutional collapse. In 2013, I reached out to Mann directly. I wanted to know: did my Rosh Yeshiva really have this backchannel relationship with one of the world’s most notorious mercenaries?
Mann’s response was classic British understatement, like something out of a Le Carré novel: “Most of that’s not about me. It could be 100 per cent right, but I don’t know.” Still, he confirmed the core of it: yes, they’d met. Yes, they’d had a relationship. Yes, it had soured. “He kept trying to do diamond deals in Angola long after he should have stopped.”
And then he dropped a line I’ll never forget. Describing his first meeting with Rabbi Elefant, Mann said the rabbi told him: “I am the Rabbi of Bethlehem. And look how great the last Rabbi of Bethlehem was.”
I could hear Rabbi Elefant saying it—a twinkle in his eye, lips curling into a grin. It summed up perfectly the improbable, one-of-a-kind connection between two men who had no business knowing each other—but somehow did.
Rabbi Elefant clearly never read the “Gedolei Yisroel” (Great Ones of Israel) memo that warned: don’t write everything down. He wrote everything down. He dictated his memoirs how he lived his life—unsanitised, unfiltered, and completely indifferent to what people might think. That’s why I treasure them. They contain insights into a vanished yeshiva world, but also Mossad missions, secret diplomacy, backroom deals, and detours, which are so strange they make you wonder how one man could contain so many contradictions.
That was Rabbi Elefant. A Brisker talmid who read CIA cables. A master of Seder Kodashim, who once offered diplomatic advice to African warlords. A Rosh Yeshiva who gave a mercenary the benefit of the doubt — because you never knew what sparks might be buried under all that gunpowder.
So, no—just to be clear—Simon Mann never became Jewish. But for one brief, unforgettable chapter in the 1980s, he sat in a sukkah with a rabbi from Jerusalem, smoked Cuban cigars, and talked about teshuvah (repentance), war, and diamonds.
And somehow, that makes perfect sense. At least, to me.
- Rabbi Pinchas “Pini” Dunner is a British Orthodox rabbi based in California
