Shannon Orand in a photo taken from her MySpace page. (MySpace.com)

A man believed to be Rabbi Leib Tropper—until recently chief of Eternal Jewish Family, a powerful group that has attempted to use millions of dollars in donations and the support of famous rabbis to control the process of conversion to Judaism throughout the world—is heard on several recorded telephone conversations doing a number of embarrassing things that run contrary to even a loose interpretation of traditional Jewish modesty and morality. The man on the recordings, who has a Yiddish accent and has been identified as Tropper by Shannon Orand, who says she recorded the tapes, is heard masturbating during phone sex, pining for someone whose breasts he hopes to “shqueeze,” and invoking Judaic teachings to justify his lust. Orand, on the other end of the conversations, responds with incredulity bordering on bafflement, like a grown-up Alice chatting with the Mad Hatter at a particularly sordid tea party.

In one exchange, the man refers to an unnamed third party who’s caught a flight on Saturday night—“motzei Shabbos”—but wasn’t quite sure he “brought the money with him.” “How does somebody travel with $3,700 and they’re not sure they have it?” Orand, who is from Houston, wonders aloud. As her Talmudic interlocutor pontificates further on the whereabouts of the money he is sending her, she makes an observation. “Maybe money is not that important to so many people,” she says, “but if I had $3,700 anywhere, in a drawer, in a pocket, in a suitcase—I’d know exactly where it is.”

How did a young single mother—who wasn’t even officially Jewish until a few weeks ago—get mixed up with a powerful ultra-Orthodox rabbi and his wealthy and influential associates? The short answer, according to Orand, is that she was in the process of converting to Judaism, and Tropper was her supervising rabbi and took gross liberties with his position. But, of course, the long answer is much more interesting.

Orand, 32, grew up in the town of Humble, Texas, a suburb of Houston, where her father was a police officer and a preacher in the evangelical congregation Assemblies of God. As Orand wrote on a Chabad discussion board, she joined her father in missionary work as a young girl and later joined his ministry. Her mother was part of the Messianic Jewish movement—Jews for Jesus is the best-known Messaniac group—and Orand became involved with Messianic synagogues as well.

Orand became pregnant with her first child while still a student in college; she later married Charles Brady Orand, 12 years her senior, who fathered her second child. She went into public relations, representing first a youth orchestra and then the real estate firm Grubb & Ellis. In 2003, when her daughter was 6 and her son was 2, her husband, a then-semi-employed technology consultant known as Brady, declared bankruptcy.

In 2006, the couple divorced after a lengthy court battle. According to Brady’s lawyer, Michael Tracton, Orand also accused Brady in court of having molested her daughter and, in 2007, Brady wound up on probation and on the Texas sex offender registry. Tracton confirmed that Orand made the accusation but says his client maintained his innocence and only agreed to be labeled a sex offender as part of a plea bargain. That same year, according to Tracton, Orand and her husband wound up back in court over visitation rights to their son. Just a few weeks ago, according to an interview with Orand on the counter-missionary website Jewish Israel, the case was decided in Brady’s favor.

As her marriage fell apart, Orand appears to have looked for a new source of faith and stability in her life. In a 2007 post on what is presented online as Orand’s personal MySpace page—one asserted to be such by two of her friends—Orand came “out of the closet,” as it is phrased there, about the faith that had been sustaining her during a difficult time. “I posted a blog quite a while back about my re-dedicating my life to G-d,” she wrote. “This re-dedication has included a lot of study, prayer, and intense research of scripture. What I discovered in my research turned my world upside down.” In an email to Tablet Magazine, Orand did not confirm or deny whether this is, in fact, her own MySpace page.

In October of 2005, the MySpace post continued, she had spent a month in Israel, hoping that when she returned she would be able “to prove one way or another that Jesus was/is in fact the Jewish Messiah”—ordering a Prophecy Edition bible, a popular Messianic version of the scriptures, and going “to work memorizing how Jesus fulfilled each and every one of the prophecies in the Tanakh (Jewish scriptures)…. surely re-affirming my faith, right?”

Instead, according to the post, she determined that she had been lied to in the religious education she received in her father’s house. “What I found when I looked deeper than the one verse references that Jews for Jesus and other missionary sites show is that EVERY ONE of those verses have either been deceptively translated or taken COMPLETELY out of context. When I started to discover this, I think I went through all of the stages of grief, and probably still am. This revelation is huge!”

After this ecstatic missive about the rejection of Christianity, she announces she was being tutored in her new faith by a group called Outreach Judaism, a group that tries to counter the work of Christian missionaries, and that she had decided to become an Orthodox Jew: “Initially, I looked into conversion, but through looking into my family discovered that I am already Jewish! I’ve written enough, so I’ll explain this part later.”

The reasons why Orand initially thought she would not have to convert, and why she subsequently changed her mind, remain unclear, as does the question of how Leib Tropper, who lives in the ultra-Orthodox enclave of Monsey, New York, became her supervising rabbi, as she contends. Orand is quite naturally reticent in her dealings with the press. “Publicity is the last thing I ever wanted. I’m simply a nobody in Houston, TX, who made a connection to a powerful Rabbi for help,” she wrote in an email to Tablet Magazine. “My only goal for the past 4 years has been to join the Jewish people, marry, and raise my children in a safe Jewish home.”

In one of the recorded conversations, the man Orand says is Tropper speaks of another man in her life. “You are heartbroken, you are destroyed, and even now you wish that he were different and you could go ahead with your relationship with him, married, not married, whatever will be,” he says in the recording. “You didn’t think about the question of whether you can marry him—he told you from the beginning that he can’t marry you because he is a Kohen.” If Orand hoped to marry a Jewish man and if, as she said in her interview with Jewish Israel, she hoped to make aliyah, then she would have needed a strictly Orthodox conversion recognized by the Israeli government—which is the specialty of Tropper’s Eternal Jewish Family organization.

A month after Orand came out as a prospective Jew, she told friends on MySpace that her job at Grubb & Ellis would most likely be ending, and that she was looking for new employment. By the end of the 2007, she was doing PR for Tovia Singer, the Monsey-based anti-missionary impresario behind Outreach Judaism as well as “The Tovia Singer Show,” a syndicated, politically conservative radio program. Orand starting attending classes at an Orthodox synagogue and volunteering with Bridge Houston, a hard-line local Zionist and anti-defamation organization, where, according to one of the group’s leaders, Ira Bleiweiss, she spearheaded a campaign against Messianic missionaries in the area, showing up in front of the Jewish Community Center, where a Messianic group evangelized each week, and taking them on, biblical verse for biblical verse.

“If there’s somebody protesting on behalf of the Jewish people around here, it’s probably because of her,” another friend from the Jewish community, Jason Levinson, said of Orand. “She very quickly has shown herself to be a hugely valuable part of our community. I see her as an up-and-coming young Jewish leader.”

Shannon Orand had transformed herself from a preacher’s daughter into an Orthodox Jew—keeping kosher, dressing according to Orthodox standards of modesty, and even sending her children to an Orthodox day school. In her online writings, she comes across as a well-spoken woman with standard Orthodox religious and political views, with special fluency in the halachic codes that govern responding to missionaries. When a commenter on Jewish Israel identified only as “Ellen” asked whether it was permissible to burn missionary materials, Oraand responded firmly. “Since my heart is so tangled up emotionally with this issue,” she said, “I have to be careful to rely only on Torah & Halacha on this….If you are a Jew, you are obligated to burn the idolatrous material.”

Her new beliefs and commitments, not surprisingly, have strained or ended many relationships from her Messianic days. One of Orand’s online acquaintances, a Jewish-turned-Messianic rapper named Aviad Cohen, suggested to Tablet that Orand’s horrific conversion experience may have been some kind of message from above. “People choose their own path instead of the path that God lays out for them and then, sometimes things like this happen,” he said.

Orand’s most significant falling-out, though, has been with the person who got her involved with the Messianic movement to begin with. “My mother, who is a devout evangelical/messianic and was never supportive of my conversion efforts, has told me that I’m going to hell and taking her grandchildren with me,” Orand said in her interview with Jewish Israel. Orand’s father, though, has taken a different path: following in his daughter’s footsteps, Orand told the website, he has left the church, and now considers himself a righteous gentile observer of the Laws of Noah, or a Noahide.

“I’ve never known Shannon as anything other than Jewish and as an observant Jew,” said Bleiweiss, who’s known her for two years. “She just has a piece of paper now, but it’s the same Shannon.”

Orand has addressed the question of why she stayed in what she says was an exploitative relationship with Tropper once it began. “I have been immersed in an ongoing legal battle involving my children and my ex-husband who sexually molested my daughter, pleaded guilty, and is a registered sex offender,” she told Jewish Israel. “Leib Tropper was taking care of the tremendous legal expenses I was incurring—which put me in a terribly difficult situation.” Later she told Tablet: “My dealings with Tropper and the decisions I made throughout this ordeal, had everything to do with protecting my children from my ex-husband, a convicted child molester who raped my daughter.” Leib Tropper refused to speak to Tablet Magazine, either to deny or confirm any of the details of Orand or others’ accounts.

Orand has said that she taped her conversations with Tropper in order to report him to the religious authorities, and that she never intended for them to go to the press. The sex tapes became public amid a legal dispute between the two major supporters of Tropper’s organization, Thomas Kaplan and his now-estranged nephew, Guma Aguiar. Aguiar—who, in addition to the falling-out with this uncle, is also now battling in court with Tropper—has acknowledged that he was one of the people responsible for publicizing the sex tapes. In an email to Tablet, Orand said she had no direct connection to Aguiar. “I want no part of that vicious war and hope that the 2 can set aside their arguments and focus their energy and money into causes that will bring peace in their own lives, and in the Jewish world,” she wrote. “Who know[s]? Perhaps peace between those two could be enough to bring about the final redemption.”

On January 3, 2010, two weeks after Leib Tropper stepped down from his post at Eternal Jewish Family and after Orand had lost her custody battle, she immersed herself in a mikvah in Jerusalem, and her conversion to Judaism was certified by four ultra-Orthodox rabbis who welcomed her into the Jewish people. “I feel like I came out of Egypt,” she told Jewish Israel a few days later.

Yet speculation about her relationship with Tropper—which, Orand maintained in her email to Tablet, never actually involved direct physical contact—have continued on ultra-Orthodox blogs, with some bloggers suggesting that the exploitation that Orand suffered at Tropper’s hands has rendered her unworthy of conversion.

“Everyone in that video [released along with the audio tapes] is tainted and questionable now, especially the women who converted,” said a commenter on the blog Daas Torah. “Its horrible to say that but everyone’s thinking it now.” The Jerusalem yeshiva bocher who runs the blog HaMekubal came to an even stranger conclusion. “If the tapes were true, there was no halachic standing for a B’’D””—a beit din, or religious court—“to be able to move forward with a conversion,” he wrote in a post that argued sarcastically that Orand’s conversion proves Tropper is owed an apology.

For those in the ultra-Orthodox world who believe that the conversion process is not strict enough, Shannon Orand is either a whore or a liar, and Tropper’s sins, real or not, are proof of the need for increased vigilance in the face of those would seek to dilute the divine essence that inhabits the Jewish people. For everyone else, the case of Shannon Orand is shocking proof of the depravity of a rabbinical establishment that gladly accepted Leib Tropper as the ultimate authority on who can rightly be called a Jew, and which still refuses to denounce his sins against the faith that they claim to uphold.

MORE: Shmarya Rosenberg at Failed Messiah today published a long interview with Shannon Orand, in which she tells her complete story. Read it here.
MORE: Tablet Magazine’s Allison Hoffman outlined the entire Tropper scandal here.
MORE: Read transcripts of the phone calls, plus hear some audio clips, here.
MORE: Allison Hoffman profiled Guma Aguiar here.