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Young Guma earned money at the country clubs as a caddy and attempted perfection on the tennis court. When he was about 13, his parents signed him up for a tennis academy in Deerfield Beach. Aguiar went to the courts every day after school and continued going after he enrolled at Westminster Academy, a strict Christian high school near his home.
Aguiar would practice relentlessly and often excel, but he would tense up after losing a couple of points, according to his old instructor, Gary Kesl. After a bad match, he couldn't forgive himself. When Ellen Aguiar was in the stands watching her son play, it seemed to distract him even more. Kesl remembers pulling Aguiar aside and telling him to imagine he was sitting at the top of the fence, watching himself get angry. Then he could accept the anger, forget about it, and focus once more on the fundamentals of the game.
When Aguiar was 18, Kesl drove him to Vero Beach for a tournament, the last boys' match of the year in his age group. The opponent was someone Aguiar had beaten in nine of ten games. Everyone expected him to win easily, but Aguiar seemed consumed by the pressure of high expectations and lost the match that day. Kesl says it hurt the young man deeply.
Aguiar, like all the other kids in Kesl's program, got into college on a tennis scholarship. But the instructor was worried about the sensitive player's future with the tough-talking coach at Clemson University. "He took things to heart... to the point that it really affected his tennis," Kesl says. Aguiar, a quick study who made good grades, dropped out of Clemson after a year.
Kaplan, his uncle, then steered him toward a few opportunities not available to the average college dropout.
Kaplan had become a successful New York commodities investor with an interest in several oil, gas, and mineral companies. He was also influential in the New York Jewish community. (Today he is president of the board of directors of the 92nd Street Y, a prestigious Jewish social club.) His success had been largely influenced by Judaism. According to a 2010 Bloomberg Businessweek profile, "In 1988, Kaplan was completing his dissertation... and earning extra money analyzing Israeli companies listed on U.S. stock exchanges. The work involved traveling to Israel, and while there, Kaplan connected with two people who would shape the rest of his life." One was his future wife. The other was an Israeli investor who became close to Kaplan and later hired him as a junior trading partner back in New York.
Just as Kaplan had been mentored, he in turn mentored his nephew Aguiar, giving him both a leg up and an education in Judaism. Like Kaplan, Aguiar studied history for a while at Oxford University. He went to work as a trader on Wall Street, near the investment firms run by his uncle. He began to work for his uncle in 2001, monitoring Kaplan's family investments.
But first, the young man had to get things straight with God.
According to Jewish law, Aguiar was Jewish because of his maternal descent. But at Westminster Academy, he'd been taught that those who had not accepted Jesus were sinners. One day when Aguiar was in his 20s, he decided to confront the contradiction head-on. He found a rabbi named Tovia Singer, who had made a name for himself by launching counterattacks at Christian missionaries looking to convert Jews.
Singer remembers receiving a call on his cell phone one evening about a decade ago. An angry Aguiar was on the phone, demanding to know how Singer justified undoing the good work of Christian missionaries. How could he read the Bible and not accept Jesus as Lord? Singer pulled into a Toys "R" Us parking lot and started a series of long conversations that would last all weekend. Aguiar argued that Jesus was the true son of God; Singer countered that he'd been falsely promoted as a messiah due to mistranslations of Hebrew in ancient texts. The two spoke on and off for the rest of the weekend, going through the Bible together, line by line. Aguiar was interested — this conversation may have provided the factual base he needed to turn back to his family's older faith.
"He took in every piece of information, and there was no emotional element about it," Singer says. Aguiar analyzed Bible verses like stock picks, looking for truth. After this research, he embraced Judaism full-on. "The change in Guma happened very quickly," Singer says.
Aguiar showed up on the doorstep of Chabad Lubavitch of Fort Lauderdale, an Orthodox synagogue near the beach, shortly after his grandmother died in 2002. Chabad Lubavitch is a branch of Hasidic Judaism that follows a series of "rebbes," or spiritual elders — something of an unusual choice for a Jew just starting to worship. He told the rabbi, Moishe Meir Lipszyc, he wanted to pray in his grandmother's memory and learn about his own Jewish background.
After the Friday-night service, Lipszyc invited Aguiar and two friends to Sabbath dinner at his house. Together they took the 15-minute walk there, because the rabbi couldn't drive on the holy day. Over dinner, they talked about the Bible. "Guma is a bloody genius," Lipszyc says. "He knew the New Testament better than I knew the Old Testament."