Ron Burkle toured the world with former President Bill Clinton, reportedly sitting in on a meeting with Nelson Mandela. The billionaire businessman spent years close to Clinton and has funneled money to numerous Democratic candidates, including Hillary Clinton during her 2008 presidential run.
But as she fights off a strong 2016 primary challenge from Bernie Sanders, Clinton has yet to receive financial support from Burkle. He even made a small — by billionaire standards — donation to Republican hopeful Marco Rubio, and reportedly held a fundraiser for the GOP's John Kasich.
Burkle has by no means pledged his support to either Republican and could still raise money for Clinton later in the cycle, a person familiar with his spending said. But his unclear allegiance so far reflects not only reports of a falling out with Bill Clinton, but also a possible desire to hedge his political bets.
Burkle declined to comment to CNBC.
Burkle founded Los Angeles investment firm The Yucaipa Cos. in 1986. He befriended Clinton in the 1990s, sometimes hosting the ex-president on his private jet. The pair eventually struck up a business partnership, which brought the Clintons at least $12 million in the mid-2000s, according to federal tax returns.
That deal ended in 2008, when Hillary Clinton first ran for president, according to The New York Times. Reports in the ensuing years indicated that Burkle's relationship with Bill Clinton cooled, though the reasons are not entirely clear.
"At this point, it's not automatic that his money or connections would be going to Hillary," said Jessica Levinson, a professor at Loyola Law School and vice president of the Los Angeles Ethics Commission.
Burkle made donations, though not large ones, to Hillary Clinton's past campaigns, according to Federal Election Commission records. He gave at least $2,000 to her 2000 Senate campaign. He then chipped in at least another $2,300 to her 2008 presidential bid.
While those donations may not be huge, the fundraisers, often attended by big celebrities, Burkle has held over the years can pack a much bigger punch.
Burkle has not yet sent money Clinton's way in 2016. His only recorded donation of the cycle so far went to Rubio, for $2,700 in December. That sum is the maximum an individual can give directly to a campaign committee, but pales in comparison to the millions mega-donors can give to political action committees.
"He probably figures Republicans have a good shot. It's not uncommon in the interest group community to hedge your bets, to support both sides," said John Pitney, a professor of politics at Claremont McKenna College, who tracks California politics.
Burkle has given to the both sides of the aisle in recent years. His largest recorded donation of $100,000 went to the Senate Majority PAC, a Democratic super PAC, in 2012. He has supported Democratic lawmakers from Dianne Feinstein of California to Cory Booker of New Jersey.
But he also gave a $2,700 donation to Republican Rep. Kevin McCarthy of California last year.
Lacking the support of a billionaire donor and fundraiser may seem like a big blow to Clinton. Instead, her fundraising machine has chugged along without Burkle.
Clinton's campaign committee has raked in more than $100 million in the election cycle so far. Outside groups supporting Clinton, meanwhile, have raised nearly $50 million.
Clinton's campaign did not respond to CNBC's request for comment on Burkle.