Late in 2011, Romney visited the Chicago headquarters of Griffin's firm, Citadel, and spoke to employees. Perhaps inspired by the gathering, dozens of Citadel workers ultimately contributed to Romney's bid for the White House.
This year, Griffin has given generously to a host of political groups, including some supporting Republican primary candidates Marco Rubio and Jeb Bush, some opposing wasteful government spending, and some supporting GOP candidates in the House and Senate.
He's the 14th-biggest political donor this cycle, according to data sorted by the Center for Responsive Politics and based on filings made through early September. But since Hillary Clinton and Donald Trump have materialized as the major-party candidates in this fall's general election, Griffin has been notably absent from the presidential race.
Welcome to the financial sidelines of the 2016 election, where megadonors like Griffin, Paul Singer, Sheldon Adelson and Richard Uihlein have so far been warming seats. Typically conservative-leaning, some of big business' most prominent political donors appear to be abandoning this presidential race altogether, focusing instead on down-ballot contenders whose victories will affect the balance of power on Capitol Hill.
Peter Thiel, the Silicon Valley entrepreneur, is a prime example: Despite urging Americans to vote for Trump at the Republican National Convention, he has yet to give the real-estate mogul a single dollar.
Instead, Thiel has given money to an Arizona sheriff running for the House, a Tennessee Republican House hopeful who was defeated in his primary, and the California state GOP, among others. A Thiel spokesman said in August that he had no plans to donate to Trump, without offering an explanation. Neither Thiel nor his spokesman immediately responded to a request for comment Friday.
There's a logic to the down-ballot strategy, especially for those who consider Trump's chances of winning the presidency low. Among the big donors, "to the extent that their interests depend upon laws passing ... holding Congress is at least as important as the presidency," said Michael Malbin, a political science professor at the State University of New York in Albany.
But for some of the sideliners, there are also practical concerns. Many believe that Trump, who is prone to mercurial rants and bullying, lacks the temperament for high office, and he isn't above bashing detractors on Twitter, a prospect that the more guarded Wall Street money managers find appalling.
More critically, Trump's anti-trade stances, which include promises to roll back the Trans-Pacific Partnership, to impose steep tariffs and to penalize U.S. companies that move operations to Mexico, concern many economists.
Clinton, on the other hand, espouses a platform of tighter regulations that rankle some financial and corporate executives. She wants to broaden the reach of Dodd-Frank, the landmark 2010 financial-regulation law, reduce tax advantages for activist investors, which would affect some major hedge funds, and lengthen the time frame under which prosecutors can pursue financial crimes.
In a late June interview with CNBC, Elliott Management founder Singer, who has indicated opposition to both Clinton and Trump, caused a stir by saying that Trump's protectionist trade policies were "close to a guarantee" of a future "global depression."
By that point, Singer had contributed millions of dollars to various political groups this cycle, including at least $5 million to a PAC supporting Rubio — a significant chunk of his $17.3 million in overall spending this election cycle, which makes him the fourth-biggest donor of either political persuasion, according to CRP figures. But after Rubio dropped out of the race, Singer's spending focused on conservative House and Senate candidates, supporting gay rights and other issues.
At CNBC and Institutional Investors' "Delivering Alpha" conference last week, Singer was more reserved. "I don't want to speak about politics at this juncture," he said. Still, he couldn't resist a veiled jab at a recent fainting spell that had afflicted Clinton. "In two months or so, we'll know the answer to … which envelope," he said, "if both of these people are still on the stage at that time." An Elliott spokesman declined to elaborate on Singer's current political thinking for this article.