…Aguiar, 15 years Kaplan’s junior, is the son of the billionaire’s older sister, Ellen Kaplan, who left Judaism to become an evangelical Christian. He was born in Brazil, but grew up in Fort Lauderdale, where he was a tennis star for his Christian prep school, Westminster Academy. Even after “returning” to Judaism, Aguiar continued to support the school, which is also his wife’s alma mater, giving it a $50,000 grant in 2007. After graduating from Westminster, he attended Clemson University, in South Carolina, but dropped out and moved to New York, where he became a clerk on the New York Mercantile Exchange. In 2001, Kaplan offered to bring Aguiar into his new business venture: oil and gas exploration. In court documents, Aguiar recounts getting into a car and driving to Texas, where he and a geologist, John Amoruso, made one of the largest onshore natural-gas finds in the past decade; as gas prices skyrocketed in the middle part of the decade, Aguiar and Kaplan’s company, Leor, attracted Goldman Sachs and Merrill Lynch as investors before selling to oil giant EnCana in 2007.
In addition to discovering large deposits of untapped natural gas, Aguiar was also rediscovering his ancestral heritage. In interviews, he likes to recount the tale of calling Tovia Singer, a Monsey-based rabbi who specializes in outreach to Jews who have become evangelical Christians, to demand the rabbi stop trying to take Jews away from Jesus. Instead, Aguiar continues, he fell in love with the Torah. In 2003, Kaplan introduced his peripatetic nephew to Tropper, who bestowed upon him the name Yehuda Dovid and took him on as a pupil in his yeshiva. Eventually, Aguiar convinced Jamie Black, his onetime high-school girlfriend, to convert to Judaism. “I thought about Jerusalem since I was a child,” Aguiar told a documentary film crew last year. “I had these amazing visions of Samson, this big strong guy, and David with the slingshot—these visions of heroes in my mind.”
Until their falling out two years ago, Kaplan and Aguiar shared both a thriving energy business—Leor was named after Kaplan’s children, Leonardo and Orianna—and a charitable organization, the Lillian Jean Kaplan Foundation, named for Kaplan’s mother and established after her death in 2002 to support Thomas Kaplan’s “philanthropic and religious goals.” From the outset, Kaplan was the principal donor to the foundation, contributing more than $1 million annually. Aguiar ran the foundation, which was registered to his home on a cul-de-sac in Fort Lauderdale, and which gave to an array of causes, including medical research and Jewish groups ranging from Hadassah, Magen David Adom, and the Jewish National Fund to ultra-Orthodox education and outreach groups, including Tropper’s yeshiva, Kol Yaakov, in Monsey.
It remains unclear why Kaplan and Aguiar, having cemented their very profitable relationship in the oil fields of Texas, decided to get so deeply involved with Tropper, a moonfaced ultra-Orthodox rabbi who first came to public prominence in his community in 2005, when he joined a group of halachic authorities who had ostracized a fellow ultra-Orthodox rabbi who had the temerity to claim that the universe might be more than 5,700 years old. No rabbi who believed that the universe predated the Jewish calendar, Tropper insisted, could be a valid judge for a conversion to Judaism—a claim that carried with it the implication that no one who believed otherwise should be allowed to become a Jew. (Tropper subsequently invalidated a woman’s conversion to Judaism on the grounds that she had later been seen wearing pants, a sartorial decision that in his binding opinion proved that she was never actually Jewish.)
Between 2003 and 2008, the last year for which documents are available, the Kaplan foundation paid out more than $8 million to Tropper’s various enterprises, helping the rabbi establish adherence to his personal brand of biblical literalism as the gold standard for Jewish belief and practice, and for conversion to Judaism. But it’s not clear how warm their relationship ever was; emails filed in one of the court cases indicate that, as early as 2004, Kaplan was losing patience with his rabbinic ally, who was demanding more money. “Your method of recognizing my generosity is to threaten withholding of your contacts, a form of spiritual scorched earth,” Kaplan wrote. “You’ve acted like a child and jeopardized the greatest project with which you could ever be associated. Quite frankly you should be ashamed of yourself.”
In 2007, after the sale of Leor closed, Kaplan and his wife, Daphne, contributed $36 million to the foundation; Aguiar, in his first contribution, added another $25 million. By the middle of 2008, as the relationship between Kaplan and Aguiar began to deteriorate, Kaplan attempted to remove his nephew—who had been drawing six-figure management fees—from the foundation. In a lawsuit pending in Florida state court, Kaplan accuses Aguiar of hijacking the foundation and distributing $7 million to certain rabbis “to further his claim he is the Jewish Messiah.”…