Updated at 2:35 p.m.

A handful of wealthy donors will be facing off in a behind-the-scenes game of electoral checkers in the 2014 and 2016 elections, spending even more money on ad buys and outreach than in the first two post-Citizens United election cycles. There's no certainty that these donors will be successful given the mixed record super PACs and 501(c)4s had in 2012, but there's no doubt we'll be seeing their influence a lot more. But who are these fundraisers, and where have their vast fortunes taken them in politics before now? This is the second in a series of profiles that will attempt to answer that question. Read the first, on Tom Steyer, here.

In a memo to investors in 2011, which stretched to 14,000 words, Paul Singer wrote that “Stability is not the way of the world."

The hedge fund CEO was talking about the financial system, but the succinct phrase also has a nice ring when applied to his political spending, of which he has done much in the past decade. It especially fits with his role as one of the foremost backers of LGBT rights on the right. Since 2010, Singer has spent more than $10 million trying to get states to legalize gay marriage and get Republicans to join the battle.

New York state's legalization of gay marriage would not have been possible without the support of four Republican state senators or the financial help of Singer and fellow hedge fund managers Cliff Asness and Daniel Loeb. Reframing the marriage debate in New Hampshire around freedom instead of equality probably played a role in the state's decision to legalize.

Singer has given more than $10 million to these different state efforts. In 2012, he gave $250,000 to Marylanders for Marriage Equality. He, former Republican National Committee chair Ken Mehlman and Paypal founder Peter Thiel hosted a anti-Proposition 8 fundraiser in New York City in 2010, organized by the American Foundation for Equal Rights. Singer has since tackled bigger battles at the national and international level.

He has given $375,000 to Americans for Workplace Opportunity to help push 48 House Republicans to support the Employment Non-Discrimination Act this year. The Paul E. Singer Foundation is working with the Human Rights Campaign to support LGBT rights across the globe. On Feb. 24, 2014, he presented an award at a Citizens Committee for New York City event to lawyers David Boies and Theodore Olson, who faced off against each other in Bush v. Gore and later won a Supreme Court case that struck down California's same-sex marriage ban -- a perfect example of the bipartisan support for LGBT rights that Singer preaches. "Ted and David’s passionate and eloquent commitment to this cause is a big part of the reason that America is in the midst of a sea change when it comes to gay rights and gay marriage," Singer said. "And it’s a change for the better." Boies and Olson are angling to have a role in the legal fight over Utah's and Oklahoma's gay marriage bans.

And, of course, there is the American Unity PAC, which Singer gave more than $1.6 million to help start last year.

The PAC backs Republican candidates who support same-sex marriage. Its goal, according to Jeff Cook-McCormac, senior adviser to American Unity PAC, is to prove there's a safe space in the political landscape for pro-gay Republicans. "Passing laws is only one of the things we need to do to win these. The other thing we need to do is make sure the Republican legislators who support these laws live to tell the tale."

The PAC supported seven candidates in 2012, and, unlike many a super PAC, they spent more supporting their candidates than opposing their opponents (albeit by not the largest of margins). However, only two of their candidates won. They're planning on spending big in 2014. Meanwhile, the American Unity Fund, the nonprofit arm of the organization, has also been working on legalizing gay marriage at the state level.

Because Singer, notoriously private and reporter-proof, has taken on a more public role with his support of gay rights, it can feel as if his other political investments have waned. But it be would be a mistake to think that. At the end of the last fundraising cycle, he continued his support for traditional Republican politicians, throwing a fundraiser for three GOP senate candidates: Rep. Tom Cotton, running in Arkansas, Dan Sullivan running in Alaska, and Rep. Steve Daines, running in Montana. The event raised $600,000. He has also donated to South Carolina Sen. Tim Scott, Texas Sen. John Cornyn and South Carolina Sen. Lindsay Graham.

Paul Singer hasn't shifted away from the kind of traditional giving that has defined much of his political involvement over the past decade. He's just diversified his portfolio of issues and allegiances.

Singer's entire career has been defined by activism. His hedge fund, which he founded in 1977, is known for taking down-and-out companies and trying to spruce them up. Before Elliott Management turned toward tough love -- like it's trying to do with oil and gas company Hess -- it collected most of its profits from distressed debt investment, a strategy that gave Singer a role as a major investor in Lehman Brothers as the firm collapsed, and currently has the fund tangling with Argentina. Although the fund doesn't invest in distressed debt much any more, it's the type of investment most associated with Singer.

In the summer of 2013, Singer told Institutional Investor's Alpha Magazine that forcing debt payment is a Singer-flavored form of activism. "We've made the point over and over again that sovereigns that could pay their debts and choose not to may be attempting to save some money but are harming their people and their economies by making investing in their countries more risky and more problematic and by discouraging foreign investment." In Singer's view, he isn't just forcing indebted companies and countries to pay up. He's trying to create a world where distressed debt doesn't exist.

Depending on your own views, that makes Singer an activist investor, or a "vulture capitalist."

Regardless of those opinions, Singer plans to continue doing this in the future -- and more of it. The fund continues to grow and shows no signs of stopping.

Singer approaches politics with a similar philosophy.

He has given more than $7.9 million to political campaigns and organizations since 1990, according to the Center for Responsive Politics, a sum which understates Singer's political involvement. His contributions to 501(c)4s and other nonprofits are not included in this number, as the Federal Election Commission doesn't require nonprofits to report their donors.

Depending on your view of campaign finance, he's either an activist donor, or an example of how campaign finance has gotten out of hand -- and many people have strong, complicated views about Singer. On the left, he has been criticized for his financial strategy and for enormous political donations. On the other hand, liberal LGBT rights activists also realize the power Singer has to push change on their issue. Marc Solomon, national campaign director at Freedom to Marry says Singer's involvement has made a "profound difference" in the movement.

"A couple of years ago," Solomon says, "most of the attention on this issue was on the side of our opponents. You'd open up the newspaper and make the automatic assumption that the power of the GOP was behind our opponents. Singer, more than anyone, has changed that narrative by putting his power, muscle, dollars, and heft behind this issue." Singer has given more than $3 million to Freedom to Marry.

On the right, those affiliated with anti-gay marriage organizations have had no qualms about criticizing Singer's attempts to advance LGBT rights in the Republican Party. Bryan Fischer at the American Family Association told Business Insider in 2012, "Here you have a super PAC that is working to chop the legs off the Republican Party platform." Many other Republicans seem to have remained silent on Singer's support of same-sex marriage. When his political investments range so far beyond that one issue, what candidate or organization would risk millions of dollars to protest?

Either way, Singer plans to continue spending in the future -- and more of it.

In both business and politics, Singer has been busy building an infrastructure that spread his goals and visions among a wider pool of people and resources, hoping to ensure the efficiency, sustainability and efficacy of both. On the political end of things, he has teamed up with other Republican donors to form the American Opportunity Alliance, a group where the big campaign spenders compare crib notes and advise donors where their money might be well spent -- whether that means political candidates, conservative think tanks or academic centers. American Opportunity Alliance's academic aims haven't received much press, but they have always seemed close to Singer's heart: He also has started the Paul E. Singer Foundation, is the chairman of the Manhattan Institute and sits on the boards of the conservative Commentary Magazine and the Harvard Medical School. The Alliance plans to "develop a conservative domestic and economic policy agenda by providing guidance to different think tanks and scholars and to people who give to those scholars and think tanks," according to a source familiar with the organization's plans.

At this point, the group has no intention of stockpiling a war chest in the manner of Koch or Rove. American Opportunity Alliance is meant for planning the future of the Republican Party purposes only. Even before American Opportunity Alliance formed, Singer was known for pressing donors to support the candidates he believed had promise, some going as far as calling him a "fundraising terrorist."

However, several of the organization's members have teamed up to hold unaffiliated fundraisers for the kind of candidates they think should be the future of the party. Last week, Singer and other donors threw two fundraisers for Republican candidates in New York City. The first one supported Thom Tillis, the House speaker in the North Carolina state legislature. He is facing a tough Republican primary, which has also drawn funding from American Crossroads. The event raised about $280,000.

The second fundraiser -- co-hosted by Sylvie Légère Ricketts, who is married to a son of one of the Republican Party's biggest donors -- supported three women running in House races, Elise Stefanik in New York's 21st District, Barbara Comstock in Virginia's 10th District and Martha McSally in Arizona's 2nd District. It raised more than $400,000. The American Opportunity Alliance had a meeting in Aspen, Colo., earlier this year where it agreed to support a diverse array of candidates, and they want that $400,000 to show they plan to follow through.

Like many political donors, Paul Singer tends to invest most heavily in issues that hit close to home. "He’s most willing to talk about issues where his experience has given him some personal insight," according to a source familiar with Singer's work.

That obviously includes his support of LGBT rights, which was first inspired by his son, who was married to his husband in Massachusetts — the first state to offer same-sex marriage.

Second, there's financial regulation, policies that directly relate to his career experience as CEO of Elliott Management, one of the most continuously successful hedge funds in history. Soon after Congress passed the Dodd-Frank bill -- of which he is a vocal opponent -- in 2010, he held a fundraiser at his house in Central Park West for seven senate candidates who had opposed the legislation. He went to Davos this January for the World Economic Forum, discussing how the banking industry has changed since the recession. At Davos, Singer admitted that his vision for how the financial industry should work will be hard, even for him. Speaking about derivatives at Davos, he said, “I love trading them. On balance, there’s been a net negative to society from this particular type of invention.”

He's not opposed to all financial regulation. In April 2009, he wrote an op-ed for the Wall Street Journal stating, "conservative opposition to any expanded role for government is a mistake. There is an urgent need for a new global regulatory initiative that addresses the primary cause of the financial collapse: highly leveraged and concentrated positions."

Third, Israel. Like fellow Republican donor Sheldon Adelson, Singer is staunchly pro-Israel. He is on the board of the Republican Jewish Coalition, which held its spring meeting last weekend. He was a member of a large American delegation that went to celebrate Israel's 60th anniversary in 2008.

He also favors immigration reform, and gave a six-figure donation to the National Immigration Forum last year.

Singer's political donations, steered by his guiding principles, picked up speed a decade ago.

In 2004, he donated $5,000 to Swift Boat Veterans for Truth. He also gave to Rep. Tom DeLay, Sen. John McCain, Sen. Arlen Specter and Sen. Chuck Schumer, among a few others. He gave more than $30,000 to Arnold Schwarzenegger's gubernatorial campaign in California the following two years. In 2006, he donated money to more than 20 candidates and committees. In 2008, his donations topped $1 million. He gave $175,000 that year to help start a petition for a California ballot measure to award Electoral College votes in the state by congressional district, which would help Republicans make inroads in the eternally blue state. Fellow megadonor Tom Steyer spent at least $177,000 on a successful effort to keep the measure off the ballot.

He gave over $3 million in 2012 -- including a $1 million investment in "Restore Our Future," the presidential super PAC investing in Mitt Romney, who himself had invested at least $1 million in Singer's hedge fund. Singer was an informal adviser to the Romney campaign and a big supporter of choosing Wisconsin Rep. Paul Ryan, the darling of conservative budget priorities, as the Republican vice presidential pick. Some members of the Romney campaign team continue to work closely with Singer.

He has given at least $100,000 to Club for Growth, a 501(c)4 that supports tea party candidates.

In 2013, Singer signed the Giving Pledge, an initiative started in 2010 by Bill Gates and Warren Buffet that enourages the wealthy to sign up to donate half of their assets to charity. The letter he wrote to explain his reasons for joining the pledge lay out a philosophy that seems to have guided his political advocacy as well -- and provides a succinct view into why his spending and public profile have increased lately.

In government, the forces of risk-aversion and constant conflict serve to stultify and narrow the range of ideas up for debate. But in the private world, philanthropists can help to nurture and spread good but neglected ideas until those in government can no longer ignore them. And when these ideas concern how best to meet urgent material needs, the power of private giving can be multiplied far beyond what is achieved by the direct provision of resources.

The long-term goals of an inclusive Republican Party and the short-term goals of a Republican Senate and White House are not mutually exclusive as far as Singer's donations go. After Singer spoke about derivatives reform at Davos, he spoke about LGBT rights with Fareed Zakaria, and he often argues that the appreciation of freedom that guides his business sense is easily applicable to same-sex marriage. He told the Washington Post last year, “Ultimately, this fight is about basic equality and individual liberty -- both conservative principles."

Frank Bruni wrote a column about Singer's support of LGBT issues in 2012. When Bruni asked Singer whether he felt discomfort from the fact that many of the candidates he showered with financial largesse were opposed to gay marriage. He responded, “I think it would be naïve of me to take this issue and just upend everything else I believe. Because I think we’re making progress.”

Tom Hamburger contributed reporting to this report.

Correction: An earlier draft of this piece said Singer had contributed $375,000 to Americans for Workplace Equality. The group is titled Americans for Workplace Opportunity.