Boston real estate entrepreneur George Krupp feels that he grew up with “three legs to the stool of Judaism” — and that all of them are now tottering. 

Those three legs, he said, were synagogues, Jewish federations and Israel. “I don’t have to tell you what’s going on in Israel and what a turnoff that is to [the younger] generation,” Krupp, 78, told eJewishPhilanthropy. “Synagogues are emptying out… and federations have seen their last. That doesn’t mean every federation is going to go bust or every synagogue is going to close down.” 

But for Krupp and his wife, Lizbeth, it meant investing their philanthropic dollars in a cause that they feel can best safeguard the Jewish future. They landed on day schools, which they believe produce Jewish leaders, and have given millions to several Boston-area Jewish schools across the denominational spectrum. In 2015, the couple gave a total of more than $11 million in matching grants to five schools, with each school raising double the amount of the couple’s grant.

Now, the Krupps have given their latest $2 million challenge grant to the Rashi School, a Reform Jewish elementary and middle school near Boston. The grant is being managed in partnership with Combined Jewish Philanthropies, Boston’s Jewish federation. Together with the $4 million in matching funds to be raised by the school, the donation is launching a $6 million endowment that will be targeted at reducing tuition for families with household incomes below $350,000. The goal is to cap tuition at the school, which can run as high as $44,500, at around $20,000 for qualifying families. 

“Going forward, what is it that the next generation of Jews are going to look to?” Krupp said. “One of the areas that we feel is very important is Jewish education, in particular, leadership.”

He added, “What we found was that the biggest issue for day schools was affordability… These schools could cost up to $50,000 a year. That’s unsustainable.”

The Krupps’ gift is one of at least two major grants announced recently that are aimed at ameliorating Jewish day schools’ long-festering affordability issues. The other is a $10 million endowment at the Philadelphia area’s Jack M. Barrack Hebrew Academy that will halve the cost of the school’s trimester program in Israel. They join similar initiatives across North America whose goal is to make Jewish education attainable for middle-income families. 

“This is an increasingly common phenomenon,” Paul Bernstein, the CEO of the Jewish day school network Prizmah, told eJP. “Otherwise you have a situation where higher-income families who can afford full tuition can pay, low-income families receive traditional financial aid, but this middle group suffers… Families in that middle income range have real pressures on affording it, including many who already place a very high premium on Jewish education.”

Rashi has several other programs that aim to ease the burden on families, from the nearly half of students who receive financial aid to a $6,000 discount per child for families where a parent is a rabbi or Jewish professional. Another program offers some students $10,000 off tuition annually in kindergarten, first grade and second grade. The school gives out $2 million in financial aid annually. 

“Families sometimes assume they aren’t the right fit for financial aid,” Ilyssa Greene Frey, the school’s director of admissions, said in a statement. “But in reality many families may be eligible for assistance through these new incentives or our traditional financial aid process.”

The endowment at Barrack was seeded in 2018 with $1 million from the Max and Bella Stein Charitable Trust, and has since raised approximately $5 million from that foundation, philanthropist Leonard Barrack and other donors, which has been matched by the Jewish National Fund-USA for a total of $10 million. 

The proceeds from that endowment will halve the cost of a program that sends many of Barrack’s high school juniors to study at the Alexander Muss High School In Israel. The program at Muss, a campus for students from abroad in central Israel that’s run by JNF, costs approximately $12,000 per Barrack student. The price tag will now be $6,000. 

Michael Stein, a trustee of the Stein Trust, told eJP that he was inspired to support the program after his daughter attended the program at Muss in 2007, and because he wants students to gain the confidence and skill to fight antisemitism and anti-Zionism when they get to college. 

“It’s an opportunity for kids to really develop a certain level of independence while still well-supported in a school,” Stein said. “We need to develop a cadre of young Jewish leaders who aren’t afraid to stand up and say, ‘I’m Jewish and I’m a Zionist and I’m proud of that.’”

For Barrack, devoting a large endowment to the Israel program in particular was important because one of the school’s goals is fostering a strong connection to Israel for its students, said Rabbi Marshall Lesack, Barrack’s head of school. Most of Barrack’s students receive financial aid for their annual tuition; the school has given out more than $3 million in tuition assistance this school year. 

“We have a goal that our kids graduate and have a deep connection to the land, the people and the State of Israel,” Lesack told eJP. “And we can do so much from here, but we have to recognize we live in Philadelphia, Pennsylvania.”

The grants in Boston and Philadelphia come amid a trend of programs to reduce day school tuition at schools in New Jersey, Montreal, Toronto, Seattle and elsewhere. Bernstein said community-wide affordability programs are preferable because they both incentivize further donations and allow parents to look at more than one school. 

“Where a community can come together and organize across several schools, it is much more effective, in part because when donors see their peers across the community giving to something like that, it’s a much greater incentive for giving,” Bernstein said. “You take away price being the driver of why someone chooses one school over another.”