He did have some brushes with anti-Semitic classmates while attending a German high school where he was one of only three Jewish students. It simultaneously led him to be closer to the other Jews and reluctant to advertise his Jewishness. “I always felt I was different” he says. “But I had no strong spiritual connection. I’d never met a religious person. In Argentina the Ashkenazim are at either of two extremes: either very religious or observing practically nothing at all.”

The school graduation trip involved a trip to Bariloche, a world-class ski resort in picturesque Patagonia. They spent a day skiing, and Leonardo fell in love with the sport. He had always been an enthusiastic, talented athlete: a brown belt in karate, runner-up in a national weightlifting championship, a finalist in a windsurfing tournament, an accomplished equestrian, and an avid participant in all manner of sports from swimming to tennis to football. He was also a daredevil who loved careening down the highways in fast cars and motorcycles — “like a maniac,” he admits. Skiing, with its combination of speed, danger, and athleticism, was a natural fit for him.

He began helping bring student groups to Bariloche as a means of spending time there himself. For several years he spent nine months a year skiing, ultimately earning a prestigious certification as an international ski instructor. He then took off to Andorra, working the winter months there as an instructor and the summer months (winter in Argentina) in Bariloche.

It was a lifestyle of the rich and famous, working with glamorous people during the days and partying with them at night. He made lots of interesting friends, easy to do in an environment of perpetual vacation. In retrospect, he admits that he must have had some special protection from Hashem, as he repeatedly put himself into clearly dangerous situations while skiing. Occasionally he’d ask himself how long he could keep up such a lifestyle, as living in ski resorts isn’t suitable for a person with a family.

He led this lifestyle till he was 28, with a one-year hiatus at age 24 to live in Miami, where he did all manner of jobs from waiter to tour guide to extra in Hollywood films. “It amazed me to see the huge sums of money invested in one minute of filming for a movie,” he would later write. “Once, we spent an entire night on one of the bridges at South Beach… with the goal of filming a car flying from one side to the other when the bridge is open.” He even worked as a magician at one point. He purchased a dove for his act; the name he chose for it would later be the same as the name of his wife.

His parents seemed content to let him enjoy his jet set life, putting him under no pressure to settle down.

Apparition of Hope

In 1998, when Leonardo was 28, he spent the summer in a resort village in Argentina. While travelling there late at night with a non-Jewish friend, on a very dark road, they suddenly saw an eerie, inexplicable spectacle: a glowing white orb, the size of a moon, traversing the sky in a matter of seconds.

Leonardo stopped the car and waited half an hour to see if it might happen again. They’d both seen it. Neither were under the influence of drugs or alcohol; in fact, they’d been in the middle of a discussion about, of all things, the pyramids in Egypt.

The glowing body didn’t reappear, but it aroused Leonardo’s curiosity. He found himself reading up on topics like extraterrestrial life, reincarnation, and alternative worlds. After spending most of his adult life on the go, steeped in the pleasures of This World and pushing the envelope where danger was concerned, he found his reading about spiritual possibilities granted him an unfamiliar but agreeable sense of serenity.

Perhaps this apparition was Hashem’s way of making him open to the next step: meeting Rabbi Leon Edery of Toronto. “He was a Moroccan rabbi who used to come to Argentina once a year to help people,” Berenstein relates. “At the time it meant nothing to me, but he had studied Torah in France and in Gateshead and had learned with Rav Aharon Kotler. My father had gone to see him about some personal matters, and urged me so strongly to go that finally I went.”

Despite his initial reluctance, he felt an immediate connection to Rav Edery, beginning with their shared name “Leon.” He found himself fascinated by the Torah he heard, and impressed by the answers he received to his questions. He ended up spending hours with the rav and accepted his Shabbos invitation.

The Shabbos invitation led to a weeklong stay at Rabbi Edery’s home in Toronto, during which he immersed himself in learning more about Torah. From there, Leonardo moved to Miami to be close to a frum community he was already familiar with. He began accepting invitations for Shabbos right and left, and found himself impressed by the family interactions he observed. It took about a year, but he finally had to start telling his incredulous old friends from Argentina that he would no longer answer their calls on Shabbos or eat nonkosher food. At one point, during a visit back to Argentina, his “friends” mocked his new observance by passing him a pork-filled empanada.

In the end he went to Eretz Yisrael, and enrolled in the Spanish section of Ohr Somayach. “Leonardo” was now known as Abraham Leib (Abraham for a great-great-grandfather, Leib for an uncle’s mother). Most of his fellow talmidim were younger than him — he was by then 33 — but he persevered. “It’s hard when you begin the teshuvah process at a later age,” he admits. “There’s a yetzer hara for older people to tell themselves, ‘Oh, I’ll never be able to learn the whole Shas.’ You start feeling like your whole previous life was such a waste of time.” (He makes sure to note that he did start learning daf yomi in 2005 for the first time, finishing Shas in 2012.)

Today, he believes the choice is clearer than ever. “The world is so free,” he says, and he doesn’t mean it as a compliment. “The divorce rate is close to 70 percent, the media is full of violence and pritzus. Young people — 16, 17 — are going out drinking and doing drugs all night. Kids come to my home and say, ‘Wow, this is so nice, such a beautiful family!’ They don’t even know this is an option.”

He looks back and feels tremendously grateful for having been spared a secular lifestyle. “Maybe today I wouldn’t be married, or I’d be divorced or married to a non-Jew. Or I’d have killed myself in a ski or motorcycle accident. Today I have five children, I’m learning and teaching and writing.”

He admits that it took time to get used to the constraints of frum life — to keep Shabbos fully, to think before you speak and act, to behave with modesty. Fortunately, he had some special role models. After Ohr Somayach he learned in Torah Ore, where Rav Scheinberg ztz”l left a deep impact on him and served as sandek at the bris of his first child. Later he went to learn in Bnei Brak and spent many years next to Rav Nissim Karelitz, often helping him put on tefillin, serving him breakfast, and learning from his way of being in the world.

About a year after coming to Israel, he was asked to help work at Retorno, an addictions center, with the cousin of a friend of his from Argentina. This young man had fallen prey to an addiction and attempted suicide several times. For Berenstein, that yearlong experience of working in a rehab center was eye-opening; he realized how many young people succumb to addictions. While growing up religious is no guarantee of immunity, he nevertheless observed that the Torah lifestyle provides a certain level of protection and at the very least provides a value system to help resist decadence and depravity. “Nothing in this world is perfect — people do fail,” he acknowledges. “But after so many years in a chareidi environment, I know Torah is perfect.”

He also maintains that teshuvah has to be done with balance and seichel. A person who had talents or passions in his pre-frum days shouldn’t have to sacrifice them if they can be pursued in a kosher way. Berenstein still goes skiing whenever he can, goes running and biking in a nearby park, and works out at a gym. “It’s just not the main focus of my life anymore,” he says. “I stay healthy to serve Hashem better.” He’s gone with groups of frum families to ski resorts in Europe, teaching bochurim to ski and drawing parallels between the need to practice to master skiing, and the need to apply themselves in learning.

On the other hand, his colorful former life serves as a useful talking point when he approaches nonreligious Jews in the course of his kiruv work. “When they see someone who was a ski instructor, an athlete, who was in movies, it breaks their stereotype about boring religious people,” he says. “Even more so, I can point to my old life and tell them, ‘Look, I did it all — I had a glamorous, fun life. But then I found Torah, and it’s even better than all that fun!’ I tell them, ‘At least see what Torah is. Once you really know what it is, then you can decide whether or not it’s for you.’ ”

Off the Slopes “I became a writer min haShamayim,” Rabbi Berenstein says. “I had begun sending out divrei Torah on the parshas hashavua online. Before I knew it, I had 500 subscribers and the list was growing. A friend suggested, ‘Make it into a book.’ That’s how my first book, Mas Dulces Que La Miel (Sweeter Than Honey), came about.”

As a baal teshuvah himself, he knew of many people who’d followed a similar path, such as a former Israeli secret service agent he’d met in Miami. “There are many people who find their way to teshuvah because their old lives led to disastrous outcomes,” he says. “But there are plenty of people, like me, who were living perfectly full, happy lives. They became religious because their souls needed sustenance. Those were the stories I wanted to capture.”

Indeed, just about every person featured in his book was a star in his field. Since Berenstein has lived primarily in South America and Israel, most of the stories are culled from those parts of the world. There’s the top Microsoft executive from Venezuela whose brother pulled him into a Torah seminar; a pediatric oncologist from Argentina; a Mexican Jew who won the national “Mr. Mexico” fitness contest; an Israeli surfer; an Israeli combat pilot. Shimi Illuzini, the well-known Israeli magician, tells his story, as does Yitzchak Fanger, who became a Buddhist Reiki practitioner and traveled to the Far East in search of more “mantras,” until his Jewish neshamah pulled him back to Eretz Yisrael. (Later, Rav Yitzchok Zilberstein would tell him Reiki wasn’t kosher, and he abandoned it.)

Some of the stories come from people whose teshuvah stories have already been publicized, although Berenstein took the stories firsthand from each source. The journey of Israeli actor Uri Zohar, for example, is in the book; so is the story of Rachel Factor, a Japanese-American woman who left a career on Broadway to convert to Judaism and now performs one-woman shows about her transformation. Alan Veingrad, who joined the NFL with the Green Bay Packers, was later transferred to the Dallas Cowboys, and after two seasons helped them win the Super Bowl in 1992. A cousin introduced him to Torah Judaism, and now Veingrad often gives inspirational speeches about Judaism. In his chapter he relates that every Super Bowl team member receives a gold ring inscribed with his name, team name, jersey number, and the number of games lost and won. As his team lost 3 games and won 16, when he sees the ring upside down it spells 613.

Then there’s Avraham Gabay, who made international news in 2004 when he and an Austrian companion went hiking in Tierra del Fuego and got hopelessly lost. Although international search teams went looking for them, they met with no success, partly because the two had wandered all the way from Argentina into Chile. Although most people would be dead after a couple of weeks in that wilderness, the two miraculously survived for 33 days until a helicopter saw their “SOS” spelled out in logs on the ground. During those weeks in the mountains, Gabay found himself moved for the first time to start observing Shabbos, praying every morning, and reading the Tikkun Klali his family had sent along with him.

Another striking story comes from Pinchas Menachem Bromson. Born and raised in Poland, he joined a neo-Nazi skinhead group, and married a woman from that milieu. To his shock and dismay, he eventually discovered that his beloved wife was Jewish. When they went to the Genealogical Institute of Warsaw to look at her family’s documents, they took a look at his, too — and discovered he was also Jewish on both sides. The shock prompted an investigation into what it means to be Jewish. Rabbi Michael Schudrich helped mentor him into a Jewish life, and today he works as a mashgiach in kashrus in Warsaw.

Berenstein wants his reading public to know these are true stories, and to even allow them to question the subjects of each chapter. Hence, he includes each person’s name and contact information in the table of contents.

He claims Hashem gave him tremendous siyata d’Shmaya in helping him locate people with great stories. He originally wrote them up hoping to influence people in the secular world, but it didn’t take long before he learned frum people were reading his book, too. “A grandson of Rav Chaim Kanievsky, who learns with me every morning after the tefillah, told me he gets chizuk from reading the stories,” he says. “Then I realized it’s good for frum-from-birth people too, because sometimes they look at the secular world and wonder if they’re missing out on something.”

His newest book, Casualidad o Causalidad? (Chance or Causation?), is a collection of firsthand Hashgachah pratis stories. It includes many charming and sometimes amazing stories of Hashem’s orchestration of our lives, from the wavering potential BT who prays for a signal he’s on the right path, then turns on the television to find a suspense film that happens to take place in front of the Kosel, to the story of a woman who mistakenly thought she needed to buy a new washing machine and ended up benefiting several other needy families as she went about her purchase.

Of all the impressive stories in 180 Degrees, I couldn’t resist asking which one is his favorite. He doesn’t need much time to deliberate. “My own,” he answers promptly.

(Originally featured in Mishpacha Issue 627)