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The Most Important Jewish Philanthropist You’ve Never Heard Of

Harold Grinspoon struggled with reading as a child. Today he’s the man behind the world’s largest Jewish book program, PJ Library.

Emily Benedek
August 19, 2020
Robert Charles Photography
Harold GrinspoonRobert Charles Photography
Robert Charles Photography
Harold GrinspoonRobert Charles Photography
This article is part of Tablet Profiles.
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“Jews have made amazing contributions to this world. But we have a 50% intermarriage rate in America. And only about one-third of the intermarried families’ children turn out to be Jews. So that, demographically, is a huge crisis. Being the crisis that it is, I thought I would devote my energy and my wealth to helping the Jewish people out.”

So said Harold Grinspoon, 91, in his homespun language, in a private video made in 2014, intended for future trustees of his eponymous foundation. Grinspoon, who might just be the most important Jewish philanthropist you’ve never heard of, is a wealthy businessman who failed at many early ventures, a Jew who doesn’t regularly attend shul, and a dyslexic who runs the world’s largest Jewish book program.

“I chuckle about it all the time,” he told Tablet recently in an email. “I was the kid who struggled with reading and spelling, but I have always loved stories. When I thought about the power of stories and conversation to pass on the richness of Jewish life, and I discovered that there were beautiful Jewish children’s books on the market, I saw an idea worth moving forward. If you are entrepreneurial, you find ways to reach your goals.”

The signature initiative of Grinspoon’s Agawam, Massachusetts-based foundation, PJ Library, sends more than 650,000 children’s books every month in seven languages to families in 27 countries who are raising Jewish children—from Venezuela to Ukraine to Australia and South Africa. Many of the families may have only one Jewish parent. They may live in towns where there are no other Jews. While some families are fully engaged in Jewish life, a good number report that PJ Library is their only Jewish resource.

Eric Robbins, CEO of the Jewish Federation of Greater Atlanta, said: “PJ Library is one of the most innovative and thoughtful ideas that the Jewish world has seen. Think of it: A gift from the Jewish community is arriving every month in my mailbox—with my child’s name on it, a book that is adding to a growing Jewish library in our home. And no one is asking me for money for it. It’s revolutionary. Also it’s nonjudgmental. You say you’re Jewish? Fine, that’s good enough for us.”

In North America, books go to children from birth through age 8. At 9 years old, children can join PJOurWay, where they choose from a selection of chapter books, graphic novels, fiction, biographies, and nonfiction until they are bar or bat mitzvah age.

Most of the books come from commercial publishers, and aren’t necessarily explicitly Jewish. PJ Library adds material on the flaps to draw out Jewish themes and to direct families to additional resources and activities. PJ Library also has its own imprint, which has produced 22 titles to date, with 10 more planned for the coming year. Providing these books constitutes outreach of the most subtle and profound kind: the occasion for a parent to read and speak intimately with her child during the few moments of calm before sleep and dreams, to spark the child’s imagination with the spoken word, and to encourage the child to ask questions—the quintessence of Judaism.

And also, to distribute the same stories to all Jewish children, no matter where they live, in hopes of establishing common bonds, the program buttresses Grinspoon’s abiding hope: “That we can hold different perspectives and viewpoints, and we can engage with our Judaism differently, but yet remember that we are one people.”

Born in 1929, Harold Grinspoon grew up in Auburndale, a village of Newton, Massachusetts. He received lessons in anti-Semitism wherever he turned—from the schoolyard bullies who called him a “Christ killer” and “Jew boy,” to the Boy Scout leader on whose door hung a sign reading: “No dogs or Jews.” His daughter-in-law Winnie Sandler Grinspoon said, “He wasn’t from a religious family, but he knew life would be easier if he wasn’t a Jew—whatever that was.”

Being Jewish wasn’t his only problem. “I was a dysfunctional child,” he recalled in his laconic Boston accent in the video. “My poor mum. I can’t spell today and I never could spell. So she took me to spelling lessons, speech lessons, posture lessons. I still can’t spell. And I had psychological problems.” He had the distinction of being the only Jewish student in the vocational track at Newton High School.

“It all started because I was born a lefty,” he explained. “And in those days, as a Jewish kid, for some reason, you couldn’t be a lefty. So my mother made me a righty.” This led to frustration, anger, learning problems, and psychological issues. Pediatricians today discourage changing the natural handedness of children; research has also shown it can lead to learning and behavioral problems, and also permanent brain changes. His self-professed inferiority complex was exacerbated by the fact his older brother Lester—who died last month at age 92—was “a genius” who became a psychiatrist after attending Harvard Medical School.

The only way Harold felt he could distinguish himself was by making money, a talent that manifested itself when as a boy he successfully sold vegetables and eggs for his father and aunt. At Marlboro College, which he attended for a couple years, he bought an old Maytag wringer washing machine and, he said, “put a 25-cent coin slot onto it. I didn’t pay for the hot water, I didn’t pay for the electricity. I just got the quarters. And that was the beginning of my entrepreneurship.”

“Not having any money growing up,” he said, “I had a respect for wealth.” His father died at 51, leaving four children behind, including 19-year-old Harold. After a variety of efforts, some successful, many not, at 30 years old, he bought a multifamily house, fixed it up, and rented it. Then he bought another, and the company he created, Aspen Square, is now one of the top 50 privately held property investment and management firms in the U.S. Basically, the company buys derelict apartment complexes and rebuilds them, turning them into attractive, well-built, successful properties. As he put it, “buying someone else’s mismanagement and repositioning them.”

After a bout with tongue cancer 25 years ago, Grinspoon began to think about his legacy: “I couldn’t just die as the guy making money. That was debasing, I thought.” He planned to leave his fortune, estimated at $500 million, for others to manage as they saw fit, but his third wife, Diane Troderman, friend Rabbi Yitz Greenberg, and business partner Jeremy Pava encouraged him to lay the groundwork for his foundation and its goals. He realized, “People with wealth have to find a home for their wealth—where they feel good about giving and what’s meaningful to them.”

And so he got to work, using his status as an outsider to ask questions, energizing the creativity of a natural lefty to think outside the box, all the while motivated by the childlike sense of wonder he still retains. And, crucial to his strengths, he is unafraid to abandon what is unsuccessful.

There was one thing he knew: He wanted to give back to the Jewish people.

“One of the things that is striking about Harold is his and the foundation’s abiding belief that there is one Jewish people,” said Rabbi Ethan Tucker, president and rosh yeshiva at the Hadar Institute. “And that in some basic sense everyone has to find a way to be connected to one another and to work together toward a shared future. Look at PJ Library—the basic claim is that every household with a Jewish child should be engaging with a shared canon. That is not only an ambition to scale a project, that is a statement of values.”

The idea for the books came to him in the mid-2000s at the Seder table of his eldest son and daughter-in-law, Winnie. When Winnie handed out books from the Israel Book Store in Brookline, Massachusetts, as afikoman prizes, Harold was struck by the enthusiasm with which his grandchildren embraced them. Winnie remembers she bought her son a book about the first Israeli astronaut, Ilan Ramon, and her daughter a book about a little girl who had immigrated to America.

Harold asked Winnie all kinds of questions: “Do they like getting books? Are there other Jewish books? Where do you get them?” A week or so later, Harold asked Winnie to buy him $500 worth of similar volumes. “I brought them over to their house,” said Winnie, “and he and Diane read them all.”

Around the same time, Harold happened to hear about Dolly Parton’s Imagination Library on NPR, and became a local funding partner. In 2005, he created PJ Library, using Parton’s partnering model. Today, PJ Library in the U.S. has 200 local partners who help the program reach families, pay for the books, and provide additional programming. “We like to say it costs a lot to be this free,” said Winnie, who serves as president of the Harold Grinspoon Foundation (HGF) and serves as a member of the board.

PJ Library also has an Israeli arm, called Sifriyat Pijama, launched in 2009, which operates in conjunction with the Israeli Ministry of Education. In partnership with the Education Ministry and Price Philanthropies of San Diego, HGF also runs a version for Arab Israeli children called Maktabat al Fanoos (Lantern Library), which is the largest Arabic book-gifting program in the world. In Israel and abroad, the books are given out in school, and then later, taken home.

Last year, HGF distributed books to 400,000 Israeli children in Hebrew and 190,000 in Arabic. To date the two programs have given 23 million books to more than 1.25 million children. Just as the same Torah portion is read every week in shuls around the world, so all of Israel’s Jewish children of the same age group in public school receive the same books. Although the program is wildly successful, nothing in Israel is easy—when choosing books, they must consider, are the clothes in the illustrations modest enough for a religious family? Will a secular family be put off by a religious theme?

Galina Vromen, head of HGF operations in Israel, said, “It took five years before we found a story on Shabbat that both conveyed the spirit of Shabbat and was suitable for the wide spectrum of families we serve. The most common theme of Shabbat books was ‘let your parents sleep,’ which was not the message we wanted to convey. Most of the rest of the books in the market were controversial for one segment of the population or another. In the end, we found an anthologized story that we turned into a separate picture book: The Missing Spice—about the specialness of Shabbat—which left the door open for families to talk about what made Shabbat special for them.”

Sifriyat Pijama is also engaged in an effort to reissue classic children’s books written by the country’s founding fathers and mothers. “One of the things that is fascinating about Israeli children’s literature,” said Vromen, is that “all the great writers wrote for children, too. It was part of the revitalization of the Hebrew language. Walt Whitman never wrote for children, but Leah Goldberg did and David Grossman does and so do Edgar Keret and Meir Shalev. We see those stories as part of the foundational stories of Israel. We talk about Israeli Jewish cultural heritage.” HGF’s mandate to create common ground also reaches to Israel’s Arab children; 20 books are common to the Arab and Jewish programs.

PJ Library expands its reach in the U.S. through its partner organizations, like JCCs and Jewish Federations, which sponsor over 3,000 PJ Library events in North America every year, further engaging families in Jewish life. And PJ Library now includes multiple book titles by Israeli authors so that American children can read Israeli stories, too.

“Books are the core of our universe,” said Winnie, but Harold also has other passions, among them Jewish overnight camps and public art. JCamp180 provides day-to-day leadership to a select group of not-for-profit Jewish camps to help make them stronger, organizationally and financially. Approximately 60,000 children and young adults attend these camps during a regular summer. (HGF recently gave a $10 million emergency infusion to aid JCamp180 member camps affected by COVID-19.)

Grinspoon is also dedicated to helping Jewish institutions shore up their financial health. He realized with distress that the American Jewish community was missing out on the largest transfer of wealth in history, a treasure that Paul Schervish, director of the Center for Wealth and Philanthropy at Boston College, estimates to be at least $41 trillion, which the baby boomers will pass on to their heirs and beneficiaries until 2052. At a conference many years ago, Harold learned of an interesting program to encourage people to make bequests to their favorite Jewish organizations.

“The insight into a legacy giving campaign,” Grinspoon explained to Tablet, came from two amazing women, Gail Litman [z”l] and Marjory Kaplan, who developed a strategy for training and incentivizing organizations to prioritize legacy conversations in the San Diego Jewish community.” Grinspoon said it took him some time to appreciate the plan’s power, but once he did, he was all in. “If we help organizations see the merit of prioritizing endowments, and if we use a gentle approach and some financial incentives to get organizations to actually do the work of asking supporters for legacy gifts to build endowments, we can help secure a stronger future,” he explained. “And many people who are asked for a legacy gift not only say yes, but they also make cash gifts today. Why? Because they were asked! People feel good about finding a place for their wealth. That includes current giving as well as after-lifetime giving. We all appreciate knowing our legacy will live on long after we are gone.”

Grinspoon brought Litman over to HGF, and in 2010, with her model, set up a new national initiative: “LIFE & LEGACY.” Grinspoon only regrets he didn’t do it earlier. He feels if he had established the program 20-30 years ago, “the Jewish day schools would be in a completely different position because they would have wealth.” Jews have long left bequests to hospitals, universities, and charities, in part because they have been aggressively courted. But Jewish institutions haven’t been as well organized. Now, Grinspoon’s LIFE & LEGACY offers training, support, and monetary incentives to motivate Jewish organizations to secure “after-lifetime commitments.” LIFE & LEGACY has 63 partner communities that work with a combined 700 organizations. In 10 years, it has secured $1 billion in legacy commitments, mostly through small- and medium-size donations. If people donate to their alma maters, why not to their beloved Jewish day camps?

Still energetic—a tall, lanky man, he is an active swimmer, hiker, and white-water rafter—Grinspoon took up sculpting six years ago. He searches out dead, leafless trunks of trees from the woods, quarters them, refinishes or paints the boughs, and reconstitutes the large-scale structures in his own way. He then places the sculpture back on its feet in nature for a second life. One might say the genius of his endeavors—the renovated apartment complexes, the creation of a common library for unaffiliated Jewish families, the development of permanent funding mechanisms for institutions in need, the resurrected trees—has been to heal what was once sundered—in himself as much as among his people.

As he reflects on his long journey in his video, Grinspoon smiles his boyish smile, eyes flashing: “I love being a philanthropist.”

Emily Benedek has written for Rolling Stone, The New York Times, Newsweek, The Washington Post, and Mosaic, among other publications. She is the author of five books.