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Republican mega-donor Harold Simmons considers President Barack Obama to be “the most dangerous man in America,” and in a bid to unseat him, fueled conservative political groups with tens of millions of dollars.

But the Dallas-based billionaire’s recent philanthropic giving has been anything but right-leaning, a Center for Public Integrity review of new Internal Revenue Service documents indicates.

The Harold Simmons Foundation in 2011 most notably contributed a combined $600,000 to an arch political foe of Republicans, Planned Parenthood, and its North Texas affiliate, IRS records show.

Simmons’ foundation also bolstered several other organizations rarely associated with political conservatives or partisan Republicans, including public television, the League of Women Voters and even a Washington, D.C.-based organization dedicated to curbing the influence of big money in elections.

The foundation’s 2011 funding came exclusively from the billionaire’s personal fortune and that of his holding company, Contran Corp. Together, they contributed more than $9.8 million in 2011 — the foundation’s only income aside from $5.6 million in investment and capital gains income. The foundation ended 2011 with nearly $52 million in reserve after distributing about $17.4 million during the year, IRS records show.

Simmons and his holding company, Contran Corp., provided major funding for Republican super PACs, including $23.5 million to Karl Rove’s American Crossroads. Simmons was second to casino magnate and fellow Republican-backing billionaire Sheldon Adelson among top donors to super PACs in the 2012 election.

Simmons or his company gave $2.3 million to the pro-Mitt Romney super PAC Restore Our Future, $1.2 million to pro-Rick Santorum Red White and Blue Fund, $1.1 million to pro-Newt Gingrich Winning Our Future and $1.1 million to pro-David Dewhurst Texas Conservatives Fund. (Dewhurst, the state’s lieutenant governor, lost a primary fight for U.S. Senate to tea party favorite and now-Sen. Ted Cruz.)

Contran Corp. also contributed $1 million to Make Us Great Again, a short-lived super PAC that supported Texas Gov. Rick Perry’s presidential bid.

Simmons’ seemingly contradictory giving patterns likely stem from an arrangement with two of his politically liberal daughters who he’s tapped to run his charitable foundation’s day-to-day operations.

While Simmons, 81, is the charity’s chairman, for more than two decades, Lisa Simmons has been approving and rejecting funding requests as president of her father’s foundation.

Sister Serena Simmons Connelly serves as the foundation’s executive vice president, IRS filings indicate. Connelly has personally donated more than $180,000 to several dozen Democratic political candidates and committees since the 2008 election cycle, including the presidential campaigns of Obama and Hillary Clinton and the Democratic National Committee.

Her father, on the other hand, gave $2 million in 2004 to Swift Boat Veterans for Truth, which ran the now-famous ads attacking Democrat John Kerry during his presidential bid.

The Simmons’ daughters declined to comment for this story, as did Contran representatives and Simmons himself.

Harold Simmons’ family life has been notoriously turbulent, fraught with divorces, lawsuits and allegations of criminality and campaign finance violations. His relationships with his four daughters are nothing if not complex.

During the 1990s, he paid two of his daughters $50 million each to settle their claims that he was misusing family trust money, according to the New York Times. Simmons remains on working terms with his other two daughters, Serena and Lisa.

The reclusive Simmons, who has vowed to give away half his wealth to charity, explained last year that the Supreme Court’s 2010 Citizens United decision prompted his expansive political giving.

“I have lots of money, and can give it legally now,” he told the Wall Street Journal in a rare interview. “Just never to Democrats.”

But Planned Parenthood, a Harold Simmons Foundation grantee, used its political action committee to donate more than $735,000 to federal candidates during the 2012 election cycle — 99 percent to Democrats.

The nonprofit Planned Parenthood Action Fund spent nearly $4.8 million on advertisements advocating Romney’s defeat, while the Planned Parenthood Votes super PAC spent more than $1.8 million on advertisements critical of Romney. The nonprofit added $1.1 million in pro-Obama advertising spending, federal records indicate.

Planned Parenthood performs abortions at many of its dozens of clinics and is a prime target of social conservatives who’ve sought to cut all government funding to the organization. Simmons has expressed indifference toward the legality of abortion, saying, “Let people make decisions on their own bodies.”

Planned Parenthood’s policy is to accept gifts and grants “for specific programs and purposes” provided that their intent is consistent with the group’s “mission, policies, beliefs, and current priorities,” according to a statement provided to the Center.

Simmons’ foundation, however, also donated $10,000 in 2011 to the Dallas-based Council for Life, a pregnancy resource charity that states it supports the “sanctity of life” and affirms that “life begins at conception.”

Mona Wilson, president of the Council for Life,declined to comment, referring questions to the Simmons foundation.

“We don’t share our donors’ information. We believe that is their prerogative,” Wilson said.

Among the dozens of other Harold Simmons Foundation grant recipients are the Human Rights Initiative, a Texas-based organization focused in large part on political asylum, violence against immigrants and human trafficking ($100,000); North Texas Public Broadcasting ($30,000); Catholic Charities of Dallas ($25,000); and the anti-death penalty group Equal Justice USA ($20,000).

The donation to Catholic Charities of Dallas helps fund the organization’s Brady Center, which provides services for Dallas-area elderly. The group also opposes abortion and provides abortion alternative services among its many programs.

“Our donors are very understanding that funding is scarce, and the Harold Simmons Foundation is entitled to make grants as it sees fit,” said major gifts officer Ashley Comstock. “We’re still grateful, and we would definitely be open to and thankful for funding we might receive in the future.”

Since 2010, the Harold Simmons Foundation has also given $50,000 to Public Campaign, a D.C.-based nonprofit that institutionally aims to “dramatically reduce the role of big special interest money in American politics.”

“I can see how it would seem ironic,” Public Campaign spokesman Adam Smith said.

Simmons’ foundation has focused its largest gifts on causes that usually draw support from across the political spectrum.

Major grants have gone to the Dallas-area arts scene and the city’s zoo and arboretum. His foundation is also in the midst of a multi-year, $50 million pledge to Parkland Hospital, a massive public facility near downtown Dallas.

On the political front, Simmons has most recently lobbed $600,000 into Los Angeles’ mayoral race, funding a super PAC that supports Republican talk radio host Kevin James ahead of the city’s March primary.

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