In 2015, Shapiro, then a Montgomery County commissioner, gave the Philadelphia Inquirer his assessment of Greenberg’s political and philanthropic work.

“He’s a major employer in the region and he’s wonderfully philanthropic — for Jewish causes, educational causes and other community organizations,” Shapiro told the paper.

Another co-founder of Susquehanna International Group is even more well-known in the world of Pennsylvania school choice advocacy: billionaire Wall Street trader Jeffrey Yass. He’s emerged as a major Republican donor nationally and an inescapable power broker within the commonwealth, despite his nearly nonexistent public profile.

Both Greenberg and Yass have been involved in bankrolling the school choice movement for more than a decade in Pennsylvania.

“We are not in this to run charter schools, to manage charter schools. This is purely altruistic,” Greenberg told WHYY in 2015, when asked about his support for Williams’ mayoral campaign. “We view this as helping kids have a choice who are trapped in failing, oftentimes violent schools.”

Along with fellow suburban Philadelphia billionaire and SIG co-founder Arthur Dantchik, Greenberg and Yass were at one point the main donors to Students First, a political action committee founded in 2010 to support school choice candidates.

Shapiro accepted $175,000 from that PAC between 2012 and 2016, according to campaign finance records. During that time, he was a Montgomery County commissioner and, by 2016, was running for attorney general.

The donations to Shapiro’s attorney general campaign so troubled Philadelphia’s teachers union that it quietly pulled its endorsement at the last minute, multiple news outlets reported.

The union declined to comment at the time, but a source with knowledge of the situation confirmed to Spotlight PA that the union pulled its endorsement over the Students First donations. (The Pennsylvania State Education Association, a larger, statewide teachers union, continued to back Shapiro in that election.)

During the 2022 gubernatorial race, PACs connected to Yass spent millions during the primary to oppose eventual Republican nominee state Sen. Doug Mastriano (R., Franklin). One of those PACs, Commonwealth Leaders Fund, ran anti-Shapiro ads during the general election but scaled back then stopped that spending shortly after Shapiro publicly pledged his support for vouchers.

Once elected, Shapiro sought to create such a program as part of the 2023-24 state budget.

“I believe every child of God deserves a shot here in the Commonwealth of Pennsylvania, and one of the best ways we can guarantee their success is making sure every child has a quality education,” Shapiro told Fox News in June 2023, late in the state’s budget process.

The remarks preceded the Republican-controlled state Senate’s sudden passage of a budget deal that included $100 million in taxpayer money to fund private school tuition for students in low-performing public districts.

But once the budget reached the state House, Shapiro received hard pushback from the lower chamber’s new Democratic majority. In a politically embarrassing setback, Shapiro agreed to veto the voucher dollars in exchange for the rest of the plan’s passage. That veto led to a nearly six-month budget impasse as state Senate Republicans claimed betrayal.

In his February budget address this year, Shapiro called on the legislature to again consider vouchers, though a top Republican leader later accused him of being unwilling to use his “bully pulpit” to get such a program across the finish line.

His ongoing support also hasn’t saved him from Yass-funded criticism.

For the past two years, a 501(c)(4) nonprofit, which does not have to disclose its donors, has spent prodigiously on ads and other lobbying to criticize politicians who don’t support vouchers.

The group, Commonwealth Action, has received significant dollars from the free market Commonwealth Partners Chamber of Entrepreneurs, according to that group’s most recent filings to the IRS. Commonwealth Partners runs two political action committees that are among the most active in Pennsylvania school choice advocacy, and both are almost entirely funded by Yass.

Between April 2023 and March 2024 — the last recorded filing — Commonwealth Action reported spending more than $973,000 on indirect education lobbying, which includes advertising and other methods aimed at shifting public opinion.

One video from last summer funded by Commonwealth Action accused Shapiro of “choosing special interests over kids.”

Commonwealth Action is linked to an established conservative organization in Pennsylvania, the Commonwealth Foundation. Since summer 2023, the exterior of the organization’s Harrisburg building, which is across the street from the state Capitol, has featured ads calling for Shapiro to pass the voucher plan. The foundation is now funding a six-figure newspaper and TV ad campaign.

“You lied, and you turned your back on us again,” Printess Garrett, a Harrisburg mother, says in a TV spot. “The only thing we have for our children is our word, and if we can’t trust in your word, we don’t have anything else.”

Moving forward, political sources told Spotlight PA they expect teachers unions and other public education advocates to be among the most skeptical of a Shapiro vice presidency.

On Wednesday, 28 education advocacy groups from across the country sent an open letter to presumptive Democratic presidential nominee Kamala Harris arguing that “it is essential that our President and Vice President be wholly committed to our nation’s public education system and willing to fight against school privatization in all its forms.”

But to Payton, not considering Shapiro for backing a policy to aid parents in the hunt for what’s best for their kids is a bad choice.

“To blatantly disqualify somebody over something ideological like that is foolish,” Payton said.