Con Game

How a New York rabbi tried to remake the rules on converting to Judaism, until a sex tape—and a family feud between his wealthy backers—brought him down


This is the first in a series.

December was a very bad month for Rabbi Leib Tropper, a powerful ultra-Orthodox rabbi who has been seeking to determine the standards for conversion in Israel and throughout the world through his little-known yet influential organization, Eternal Jewish Family. First, black-and-white posters appeared on walls in Jerusalem and other Israeli cities threatening public disgrace if the rabbi refused to “cease his filth.” While the definition of “filth” was left up to readers’ imaginations, photos and video were prominently mentioned in the text, which demanded that Tropper suspend his involvement in performing religious conversions.

On December 14, Eternal Jewish Family—which is based in the ultra-Orthodox enclave of Monsey, New York, and backed by the billionaire board president of New York’s 92nd Street Y, and his nephew, who owns one of Israel’s most famous soccer clubs—suddenly announced that its founder was resigning his post to “pursue a variety of other interests,” the details of which were again left to readers’ imaginations.


Two days later, the filth appeared online: audio tapes, allegedly of the rabbi, trying to coerce a single mother from Houston into having sex with other men for money—and as the price of her conversion to Judaism.

“Would you have a problem with just talking about sex to a guy, or only actually doing it?” the man asks on one of the tapes. In another, he reassures her, “I could roleplay a rape with you, but I couldn’t actually rape you.” A third featured explicit phone sex between the two. Shortly after the tapes surfaced, the hopeful convert, a minister’s daughter named Shannon Orand, told the blogger Shmarya Rosenberg—who has covered the story on his blog, Failed Messiah—that the rabbi had said, “If you fulfill my needs, I’ll fulfill yours—and you need a conversion.” Through an attorney, Tropper released a statement that admitted no wrongdoing but expressed regret for “what has appeared to be conduct not within our significant laws of modesty.” (When Tablet Magazine reached Tropper by phone at his home in Monsey to request comment, he simply said, “No, no,” and hung up.)

The sex tapes appeared to support the allegations of misconduct against Tropper, and they briefly elevated what started out as internecine rumor-mongering among ultra-Orthodox factions into legitimate tabloid fodder. (“Tal-Mood for Love,” read the headline above a brief item in the New York Post.) To more sensitive listeners, the tapes exhibited not just the particular sexual perversions of a rabbi from Monsey, but also the moral horror of a religious figure exploiting the trust of a woman who was hoping to join the Jewish religion and who was dependent on his authority. (Orand completed her conversion in Jerusalem last week under the auspices of a different Orthodox rabbi.)

Other than the mention in the Post, mainstream American newspapers ignored what is surely one of the weirdest, most embarrassing, and most consequential scandals in recent Jewish history. Mainstream rabbinical and Jewish communal organizations in the United States also chose to be silent. Yet the rise and fall of Leib Tropper raises fundamental questions about the abuse of a closed process in which a small group of ultra-Orthodox authorities are allowed to set their own binding terms for conversion to Judaism using the authority of the State of Israel and without any meaningful oversight. It is also the story of how an almost unknown rabbi managed to become one of the most powerful authorities on the question of conversion, fueled not by a superior knowledge of the Talmud but by access to something that appears to be even dearer to the hearts of the modern rabbinical establishment: money.

Tropper is a rare figure in the Jewish world: a creature of the insular ultra-Orthodox community whose relationships tie him to Texas oil fields, professional sports teams in Israel, and mainstream secular Jewish organizations—specifically, the 92nd Street Y, one of New York’s best-known Jewish community institutions, and home to one of the city’s most exclusive preschools. After spending more than two decades toiling in relative obscurity in Monsey, Tropper catapulted four years ago into the milieu of Israel’s powerful ultra-Orthodox rabbinate, propelled by his two powerful and wealthy patrons: Thomas Kaplan, the billionaire oil and mining wildcatter, and his nephew, Guma Aguiar.

Now 32 years old, Aguiar was born to a Jewish mother but raised as an evangelical Christian. Kaplan—the younger brother of Aguiar’s mother, Ellen—introduced Aguiar to Tropper in 2003, after Aguiar had already begun exploring Judaism. Under the rabbi’s tutelage, Aguiar adopted a Hebrew name—Yehuda Dovid—and, in 2007, made aliyah to Israel, where he has become a celebrity, thanks to his recent investments in the Beitar Jerusalem soccer team and Hapoel Jerusalem, the city’s basketball franchise. Kaplan and Aguiar cemented a philanthropic relationship with Tropper by directing millions of dollars to his Eternal Jewish Family. That money, in turn, enabled Tropper to influence determinations of which rabbis would have the authority to perform conversions—that is, to determine who is and who is not a Jew.

“On a personal level, he was not particularly well respected,” said Rosenberg, who is a fierce critic of the ultra-Orthodox world on his blog. “But insert EJF and conversions into it, along with Tom Kaplan’s money and Guma’s money, and suddenly Tropper became one of the most powerful rabbis in the world.”

Tropper’s relationship with Kaplan and Aguiar, once the source of his power, ultimately played a role in his undoing. For the past year, the two men have been locked in an Oedipal court battle over the $2.55 billion fortune resulting from the 2007 sale of their natural-gas exploration company, Leor Energy, to the oil giant EnCana. Tropper agreed to appear as a witness for Kaplan, and, in response, Aguiar turned against his former mentor. According to Tropper’s wife, Laurel Blond, Aguiar made a phone call to the rabbi’s house in March in which he claimed he had “thousands of rabbis praying for Tom Kaplan’s death” and encouraged the rabbi to “switch sides.” In early April, Aguiar confronted Tropper in Jerusalem at the David Citadel Hotel and, according to court records, threatened to throw the rabbi off a ninth-floor balcony.

Then, in October, Aguiar sued Tropper in an Israeli court, claiming that the rabbi misappropriated donations. “He had gone to Rabbi Tropper for several years as his rabbi—he had confidential discussions with him, he was his spiritual advisor,” Aguiar’s lawyers told a federal judge in Florida last June. (Kaplan’s attorney, Harley Tropin, said in a statement that Kaplan would not comment on the Tropper scandal in light of ongoing litigation.)

When the sex-tape scandal broke last month, Aguiar was among those who forwarded the audio recordings of Tropper’s conversations with Orand to Failed Messiah’s Rosenberg, ensuring that the rabbi would be publicly humiliated. In a phone conversation with Tablet Magazine, Aguiar initially said he forwarded the audio “to some people because I thought they were funny,” but subsequently said he only sent the recordings in response to a request from Rosenberg. “There’s no such thing as revenge,” Aguiar said. “It’s just exposing the truth.”

Aguiar said Kaplan introduced him to Tropper in 2003, after he had already begun studying Judaism with another Monsey rabbi, Tovia Singer, who specializes in reaching out to evangelical Christians who, like Aguiar, were born Jewish, and getting them to “return” to Judaism. With his uncle, Aguiar was instrumental in prompting Tropper to expand beyond his work with baalei teshuva—returning Jews—into the world of conversions. (Aguiar’s wife, Jamie, whom he met in high school, is a blond former evangelical Christian who converted to Judaism.) By 2004, according to emails filed in one of the federal court cases, Tropper had started writing a manual designed to streamline conversions among the various religious courts in America. That year, Kaplan’s foundation gave Tropper’s organization $154,000; the next year, Kaplan and Aguiar directed more than $700,000 to the rabbi’s group.

In early 2006, Tropper told a reporter that EJF was going to offer “Cadillac conversions” to non-Jews who were concerned about making sure their conversions—and, particularly for those converting to marry, their children’s status as born Jews—would be recognized by religious authorities in Israel, where full citizenship depends on it. Tropper offered a clever soundbite: “Why settle for a broken Chevy, which may go down the highway but nobody wants it in their driveway?”

The timing for Tropper’s new product line couldn’t have been better. A feud that had been simmering for years between Israel’s insular, powerful rabbinate and American rabbis erupted into full-scale war in April 2006, when Shlomo Amar, Israel’s Sephardic chief rabbi, announced that he would not automatically recognize conversions approved by the Rabbinical Council of America, the main union of Modern Orthodox rabbis. (The Israeli chief rabbinate does not recognize any conversions, marriages, or other rabbinical functions performed by Reform or Conservative rabbis, on the grounds that the Reform and Conservative movements do not recognize halachic authority and hence are no longer branches of Judaism). Amar’s announcement created a groundswell of interest in Tropper’s Cadillacs, and the rabbi spent lavishly to promote his brand of specially certified conversions to the ultra-Orthodox rabbinate. According to financial records, in 2006 Tropper spent $1.6 million—more than double his previous year’s budget—hosting conferences and paying for rabbis to attend his educational programming, including a lavish Jerusalem summit in July 2006 at the five-star David Citadel devoted to “Improving Conversions and Preventing Intermarriage.” Amar turned up, along with Ashkenazic Chief Rabbi Yonah Metzger and Rabbi Yosef Shalom Elyashiv, a nonagenarian considered to be one of the ultra-Orthodox world’s leading halachic authorities.

Overnight, the rabbi from Monsey had become a major power broker in the ultra-Orthodox world in both America and Israel. In 2007, the last year for which federal tax records are available, Tropper distributed $2.3 million in scholarships and hundreds of thousands of dollars more in unspecified travel and conference accommodations from his Monsey redoubt.

Tropper has been removed from his post at Eternal Jewish Family—which is still chaired by Kaplan—and, according to the group’s executive director, Rabbi Dovid Jacobs, has also been replaced at Horizons, EJF’s parent organization. It isn’t clear whether he remains in control of his yeshiva, Kol Yaakov; a person who answered the phone there Tuesday refused to comment. But in the weeks since Tropper’s downfall, no one in the ultra-Orthodox world has been willing to officially criticize or reprimand the rabbi for what appear to be his profound and sickening sins. At a December meeting, the Council of Torah Sages, the halachic body of Agudath Israel, an ultra-Orthodox umbrella group, discussed the scandal but decided against issuing a comment. Only the Modern Orthodox Rabbinical Council of America has condemned Tropper’s behavior: “What we have heard, if true, violates the fundamental elements of all that Judaism holds sacred,” the council said in a statement, adding that the rabbis welcomed any of Tropper’s victims for counseling.

“It’s like Nixon,” said Tovia Singer, the rabbi who initially sparked Aguiar’s interest in Judaism. “The damage has obviously been done to the haredi community and the more that they’re in denial the more damage it’ll do.”