Deborah Simon, a political junkie, was particularly troubled when Mike Pence became vice president, people familiar with her thinking said.

| Ethan Miller/Getty Images Elections Shopping-mall scion sisters have a beef with Pence and millions for Democratic candidates The pair has poured $12 million into backing Democrats, making their combined contributions the seventh largest chunk of cash donated to either party this cycle.

A pair of shopping-mall scions from Indiana might seem like unlikely champions of the Democratic resistance.

But sisters Deborah Simon and Cynthia Simon-Skjodt — who have for years opposed Mike Pence in Indiana over abortion and religious freedom laws — have poured $12 million into backing Democrats, making their combined contributions the seventh largest chunk of cash donated to either party this cycle.


The Simon sisters, as these members of Indiana’s most famous business family are called around Indianapolis, are still relatively unknown figures on the national stage. But their turn to big-league giving, mostly to help Democrats retake the Senate, comes after years of donations to progressive nonprofits such as Planned Parenthood and the Anti-Defamation League — and as Democratic donors have gone into hyperdrive after the election of President Donald Trump.

Billionaire Tom Steyer, the country’s biggest single spender on politics, plans to spend $30 million more this year than he did in 2016; LinkedIn founder Reid Hoffman launched a fund that collects money from other people to invest in both campaigns and private companies.

The Simons, too, were fired up by the success of Trump — and his running mate, friends of the family and Indiana operatives said in interviews with POLITICO. The sisters, who generally avoid media attention, did not respond to requests for comment.

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But their focus on progressive causes in Indiana is well known in political circles. The state has long hosted fiery debates over how the government should address social issues such as abortion, gay rights and sexual assault, and the Simon sisters donated millions of dollars to left-leaning nonprofits.

Pence, meanwhile, pushed for cutting off federal funds for Planned Parenthood during his career in Congress, becoming a conservative star in the process. In 2015, after he became governor of Indiana, Pence signed a law allowing companies to deny service to individuals if they said it would burden their freedom to exercise their religion, enraging the state’s business community, including the Simon family.

Deborah Simon, a political junkie, was particularly troubled when Pence became vice president, people familiar with her thinking said.

“If you care about reproductive health care, which Debbie does, this is a guy who spent 12 years of his career” voting to defund Planned Parenthood, said one Indiana political operative. “He was willing to shut down the federal government over it.”

The Simon sisters donated $48,700 to federal candidates during the last midterm elections and gave $41,500 to candidates for state office, who have always received more of their attention. During the 2016 elections, they donated $152,000 to federal causes and $230,500 to candidates in Indiana, the bulk of it in the form of a single donation to lieutenant governor candidate Christina Hale during the final weeks of the campaign, according to state campaign finance records.

But the spring after Trump and Pence were elected, each sister donated $1 million to Senate Majority PAC, the main super PAC aligned with Senate Democrats — a down payment on reelecting home state Sen. Joe Donnelly and helping Democrats take back the chamber, according to multiple people familiar with the donations.

The sisters have now donated a total of $5.5 million to Senate Democrats’ PAC and have given millions more to the political arm of Planned Parenthood, the Democratic National Committee, American Bridge 21st Century and the Democratic Senatorial Campaign Committee, among other organizations.

Deborah Simon has also begun thinking about how to get involved in the 2020 elections, the Indiana operative said.

The 2016 elections “convinced them that we need to be energized,” said Indiana businessman Jeffrey Smulyan, a longtime family friend. “You look around, you see where the United States is and what’s happened in Washington and say, ‘You know what, it is the time to get energized.’”

Like Pence, the Simons have long been a household name in Indiana, due both to their family’s booming mall business and its patronage of Hoosier basketball.

Cynthia Simon Skjodt and Deborah Simon’s father, Mel Simon, began leasing and buying real estate in the 1950s with his younger brother Herb and eventually built Simon Property Group, which developed major projects such as Mall of America and now brings in $5 billion in revenue each year.

In 1983, the brothers bought the Indiana Pacers, and Herb Simon owns them today. The brothers donated tens of millions of dollars to Indiana universities and politicians and to national figures such as Bill and Hillary Clinton.

For local politicians, Simon properties are literally hard to ignore. The Simon Property Group headquarters is perched directly across a grassy courtyard from the statehouse in Indianapolis. In the lobby, operatives and reporters mix with lawmakers at the popular Cafe Patachou — where they can sometimes order a cup of the Simon Blend.

Mel Simon died in 2009, sparking a legal battle between Deborah Simon and her stepmother, Bren Simon. Deborah Simon alleged that Bren Simon had coerced her ailing husband into changing his will during the final months of his life in a manner that dramatically reduced his three children’s inheritance. Bren Simon said her husband had agreed to the changes to the will because he wanted to compensate her for the loss in Simon Property Group’s stock value due to the financial crisis. The court battle stretched on for three years and ended in an undisclosed settlement in late 2012.

Deborah Simon and Cynthia Simon Skjodt ramped up their giving after the settlement. In 2013, Cynthia Simon Skjodt donated $40 million to Indiana University’s basketball stadium, which was rechristened the Simon Skjodt Assembly Hall. That same year, Deborah Simon gave $100 million to her high school alma mater, Mercersburg Academy.

Friends say the two were involved in progressive causes even before their donations became noteworthy.

Deborah Simon pushed her local chapter of Planned Parenthood through a difficult $7 million capital campaign. “Debbie often refers to the two red letter days in her life — when she first exercised her right to vote and the day the Roe v. Wade ruling was issued,” the local Planned Parenthood newsletter said when introducing Deborah Simon as its board chairwoman.

People close to her say it was Pence’s push to defund Planned Parenthood — he told POLITICO in 2011 that the organization “ought not be in the business of providing abortions” if it also wanted to continue counseling and HIV testing — that put him on Deborah Simon’s radar.

Then, in 2015, after he became governor, his decision to sign the Religious Freedom Restoration Act aggravated the Simon family, according to multiple people who discussed the issue with family members.

The Indiana Pacers and the WNBA team, the Indiana Fever, bashed the law. "Everyone is always welcome at Bankers Life Fieldhouse," Herb Simon said in a statement. "That has always been the policy from the very beginning of the Simon family's involvement, and it always will be."

When Pence launched his reelection campaign — which he abandoned after joining Trump’s ticket — the Simon sisters donated to his opponents, John Gregg and Hale. That year, Trump and Pence swept the state by nearly 20 percentage points, carrying every county except Marion (home to liberal Indianapolis) and a handful of others.

The Simon sisters, like many Democrats, were deeply troubled by the election results, friends and associates told POLITICO, and the following spring they started routing donations to Indiana candidates — including Donnelly, who had courted their support — and the Democratic National Committee.

“They’ve found they can help philanthropically, whether it’s supporting a domestic violence center, Planned Parenthood, or women survivors of assault,” Hale said. “But in terms of long-term need, and to set people up for success, they have to get involved politically.”

Strategists familiar with the Simons said they want to flip the Senate to Democrats’ hands.

At the same time, they want to make clear to red-state Democrats like Donnelly that they shouldn’t shy away from liberal priorities, such as defeating Supreme Court nominee Brett Kavanaugh, who Democrats fear would vote to overturn Roe v. Wade.

The donations are “an opportunity to make clear, these would be our preferences in terms of how you behave [when it comes to] Kavanaugh,” the Indiana strategist said.

