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t was late on a Tishah B’Av morning when a call came in to the cell phone of Rabbi Yisroel Grossberg, principal of Bnot Chaya Academy (BCA), the alternative Brooklyn high school for girls for whom there is no alternative. On the other end was a student of his with an urgent inquiry. “Rabbi, what time is Tishah B’Av over?” He gave her the break-fast time and then asked if she was indeed keeping the fast, to which she replied, “Yeah, we’re all here on the beach, not swimming, just talking, and we’re all fasting.”

The next day she called again, this time to tell her principal how much it had meant to her that she could call with her question, explaining that she and her friends had been sitting around on California’s Venice Beach when they decided to “do Tishah B’Av.” The problem was none of them had any idea when it ended — and no one had anyone in the world they felt they could call to ask, not parents, not anybody. Then this girl had spoken up: “I have a rabbi I can call.”

That fall, at the first staff meeting of the new school year, Rabbi Grossberg retold the story of the Tishah B’Av phone call from the beach, adding, “What’s our job? To be that person on the other end of the line.”

For Reb Yisroel, the phrase “24/6 availability” isn’t a cliché but a reality, and there are all kinds of calls: “A girl called me late one night and said, ‘Rabbi, I have good news and bad news. The good news is I feel literally like you’re my father. The bad news is the cops said to call my father, so I’m calling you…’ ” There are the 3 a.m. calls about family fights and shoplifting and drug overdoses, which he describes in his understated way as “not pretty.”

I arrive at the school, which is in a large shul building just off the busy Coney Island Avenue thoroughfare in Flatbush, Brooklyn. If you expected Rabbi Grossberg to fit your mental image of the head of a school like this one: youngish, smooth-talking, on the cool side — you might want to file those preconceptions away.

A talmid of Mir and Lakewood and a longtime yeshivah rebbi and menahel who counts the legendary mashgiach, Rav Shlomo Wolbe, as his primary influence in chinuch, the 48-year-old Reb Yisroel might not fit the image of a compelling, with-it kiruv rabbi. But the gifts he brings to this most difficult of jobs are immediately apparent: a calm, down-to-earth demeanor, a mix of genuine warmth for and appropriate distance from his charges, and an unshakeable belief that nothing makes one happier and emotionally healthier than living Jewishly.

He doesn’t claim to have all the answers or a ready supply of sharp one-liners; he often says that “if any of these gurus tell you, ‘this is the answer,’ run away from them.” But what I learn on my visit to BCA is that the girls who come here don’t want or need pat answers, anyway. Instead, they’re seeking an open atmosphere in which they can be honest about their struggles, a place where, for perhaps the first time in their lives, they know the people here care more about them and their success than about what their behavior or appearance says about the school.

“It’s interesting,” Rabbi Grossberg tells me, “I once spoke to a parent about his daughter’s issues, and years later, at this girl’s chasunah, the father cried as he thanked me. I thought to myself, I don’t remember ever giving this father any earth-shattering advice. But as the father told me, ‘You listened to me and you heard me and that was worth more than anything in the world.’ ”

Established a decade ago by Ohr Naava founder Rabbi Zecharia Wallerstein, BCA is still the only high school–level program in the country for girls who find themselves without a school due to their personal struggles: severe family dysfunction, abuse, mental health problems, drug use, involvement with the opposite gender, and more. The school remains under the constant guidance of Rabbi Wallerstein and Mrs. Chani Segall, a legend in the field of dealing with at-risk teens. But to describe it as a school for at-risk girls, Rabbi Grossberg points out, is simply inaccurate: “These girls are not off the derech — they were never on the derech. That’s a big distinction. It’s not that they got the genuine product and chose against it; they were never given it. And when they’re given the real thing, hopefully they’ll be ready to accept it.”

The central thing girls are lacking when they arrive at BCA, according to Rabbi Grossberg, is any sense of connection to Hashem, which is not the same thing as belief in Hashem. Emunah issues aren’t their main struggle. In fact, when the school brought in a professional speaker on the topic of emunah, the girls were incensed. “You think we don’t believe in Hashem?! You don’t have to bring in someone like this!” Only when the principal explained that this speaker makes these presentations at schools of all sorts were the girls mollified.

The school’s goal, then, is to encourage its students to find their own personal path back to the Ribbono shel Olam. That path might very well be different from that of their parents, considering that BCA draws students from across the Orthodox communal spectrum, including from chassidic homes. “We’ve had girls here from Satmar homes who are now living in Tzfas, wearing long, flowing peasant skirts,” Rabbi Grossberg says. “One girl sent me a picture of her Breslover chasunah in Eretz Yisrael, and I thought, ‘I’ve seen brides dressed in white, and now I’ve seen a wedding where the bride and groom are in white.’ But that’s the path back that she found. When it’s personal between you and the Ribbono shel Olam, nothing can compare to that.”

Like His Own Daughters

So, is the school’s primary focus to help its students create functional lives for themselves, or to return to observant life? He acknowledges the dilemma, quoting Rabbi Wallerstein’s line that the school doesn’t exist “to create sober goyim.” So a reintroduction to Judaism is very much a part of what takes place at BCA, but it’s done with intelligence and nuance, taking into account where these girls have been and what they’re up to now. In Rabbi Grossberg’s experience, when everything else in a girl’s life is in place, the Yiddishkeit falls into place of its own accord, “because they want it. Who doesn’t want it? It’s beautiful. We just have to set the stage for it.”

Early in his tenure at BCA, a girl asked him, “Rabbi, I smoke while listening to my iPod on Shabbos. I can’t stop doing both, because my nerves couldn’t take it. So is it worth anything if I give up one of them?”

He replied that although he didn’t know the answer, “one thing I can tell you is that if you’re giving something up for the Ribbono shel Olam, I can’t believe it’s not meaningful up in Shamayim.”

After all, he explained, imagine we were to substitute “father” for “G-d”; if someone’s doing two things that cause pain to her father, do you think he wouldn’t be happy if she stops doing one of them? When Rabbi Grossberg told Rav Shimon Alster, rosh yeshivah of the Yeshiva of Cliffwood and his main source of guidance, about this exchange, Rav Alster said, “You did good.”

With both feet still firmly planted in the yeshivah world — for years, he has spent his summers in the Catskills at Camp Tashbar, giving shiur to ninth-grade boys from top yeshivos — it wasn’t a given that he and BCA were a good fit. He was fresh from a decade’s worth of chinuch experience in Brooklyn’s Yeshiva Derech HaTorah, first as a rebbi and later as principal of its elementary and high school divisions. He’d been preceded at BCA by a female principal, and when the girls heard a rabbi was taking over, they were very unhappy.

The girls there tend to be brutally blunt, and during his very first week, a girl said to him, “Rabbi, it’s nothing personal, but we’re going to make your life miserable.” She continued, “Do you know what a trigger is? Well, to us, you’re one big walking trigger. Your beard, your hat… it’s not your fault, but you represent everything that’s painful to us. So it’s going to be miserable for you here.”

Seven years later, he’s still here, because he provides precisely what the girls need: a model of healthy frumkeit, someone the girls see as “real” — the highest compliment one can get in BCA — and whose connection to HaKadosh Baruch Hu is genuine, yet not flaunted.

And two years ago, Rabbi Grossberg’s plate of communal responsibility got even fuller when he became the rabbinic advisor for Chazkeinu, a peer-led organization for women struggling with mental illness. The group’s members, he observes, are regular people in the community — “your neighbors,” as he puts it — who are functioning in daily life, but are also under care for something somewhere along the spectrum of mental illness. He recalls the first time he spoke at a Chazkeinu event: The only people there were volunteers doing the setup and he kept wondering, “When are the people with mental illness going to come?” Then the program began, and the people who’d been setting up took their seats, and it dawned on him — these were the people with mental illness.

In his role at Chazkeinu, he addresses the interface between Yiddishkeit and mental health, whether in the twice-weekly phone-in support group led by mental health experts, in the shiurim he gives before the Yamim Tovim (“each of which,” he says, “comes with its own issues”), or answering medication-related sh’eilos on Erev Yom Kippur — when his phone rings off the hook, because many women are uncomfortable asking such questions of their own rabbanim.

Rabbi Grossberg is the rare mechanech who has endeared himself equally to his staff and students. Dr. Sara Miller, BCA’s clinical psychologist, speaks of Rabbi Grossberg as the “soul of the school” for the way he treats each student as his own daughter, balancing her needs with what can sometimes be the conflicting needs of the school.

Reb Yisroel still finds meaning in something the well-known mashpia, Rav Shimon Galai, told him soon after he joined BCA: “These girls need to understand that there is a Ribbono shel Olam, and for that they need to understand the concept of an abba. You will be that abba who enables them to know HaKadosh Baruch Hu.”

Rivky, a second-year student, recalls coming back from the Pesach break a day early to find the dorm closed. She was in a public park at 2 a.m. and expecting to finish the night there when “the Rabbi” showed up and opened the dorm just for her.