He's taken money from a lengthy list of international donors and at times supported foreign countries in ways that are at odds with or impact U.S. policy.
With financial and political interests across the globe, former President Bill Clinton's ties raise a unique set of questions about the potential overlaps and conflicts of interest should his wife be nominated as secretary of state.
Though the Obama team is working to vet Bill Clinton's interests, it may be nearly impossible to fully insulate Hillary from her husband's broad international reach, experts say.
"All these special relationships that Clinton has brings up issues of conflict of interests between the public trust of the United States and what is in his private interest," said James Thurber, the director of the Center for Congressional and Presidential Studies at American University. "You cannot easily separate his interest from her interest, because they're one unit. They're married, so it's a serious problem."
A spokesperson for Clinton declined to comment as did a spokesperson for the Obama transition team.
During Hillary Clinton's presidential bid, Bill began divesting himself from some foreign ties, in particularly his relationship with Yucaipa Cos., an investment firm run by campaign donor Ron Burkle. Of concern was Clinton's partnership in the company's global investment fund, along with Burkle and a company closely tied to the ruler of Dubai.
And it's not as if Hillary hasn't dealt with any of these questions before. "This is a woman who has been a U.S. senator and a presidential candidate and potential conflicts that come up are not brand new things to her," said Maryle Boyle of Common Cause.
But it's not just Bill Clinton's financial ties that pose problems for Hillary. As someone who speaks regularly with world leaders, the former president would have unusual stake in the outcomes of his wife's policies.
Questions About Bill's Business Deals
Some of the biggest questions stem from his reported involvement in business deals that are at odds with U.S. policy or his wife.
The most widely cited example are reports that Clinton traveled to Kazakhstan in 2005 with a major mining investor, Frank Giustra, and pledged support to the president's interest in heading an international election monitoring organization -- despite criticism from U.S. officials, including his wife, on the country's human rights record.
Within days of the trip, Giustra's company landed a multi-million dollar deal to buy into Uranium projects with the Kazakhstan. Months later, Giustra donated $31.3 million to the Clinton foundation. Clinton's spokespeople have said that Clinton was unaware of any specific business plans Giustra had and he has said that his relationship with the former president did not affect his business.
Another instance involved Bill Clinton's role advising Dubai World Ports when its bid to win rights to run ports in the United States invoked a firestorm of domestic criticism. According to the Financial Times, Bill Clinton advised the company to allow for an intensive investigation into the company, something supported by the White House. But at the time Hillary Clinton was vocally opposed to the deal.
Outside of his business dealings, Bill Clinton's library has received millions from donors, many of whom have never been made public. The former president has also raked in tens of millions of dollars for speaking engagements around the world. While many have been disclosed in the Senator Clinton's annual ethics filings, exactly how much Clinton has collected for speaking engagements on behalf of the foundation is not publicly known.
"There is the issue of transparency generally," says Sheila Krumholz, executive director of the Center for Responsive Politics. "There would have to be a sense that there are no business dealings that could cause concern. If it's secret and there are no limits I think that would draw scrutiny and criticism."
Questions About Clinton Library Donors
Indeed, some of the already known library donors have raised questions. Two came from individuals connected with campaign finanace scandals, according to reports in the New York Times. The first donor was Farhad Azima, who promised to give the library $1 million. Azima, an Iranian-born aviation executive, had a donation to the Democration National Committee in 1997 returned because his company flew military equipment to Iran in connected with with Iran contra scandal. The DNC, however, ultimately accepted the money.
Another library donation that raised eyebrows was the $1 million from Eric and Patricia Hotung. After Patricia, an American citizen, pledged $100,000 to the Democrats, her husband, a Hong Kong businessman won a meeting with Clinton's national security adviser in 1997.
Members of the Saudi royal family, Arab businessman, and governments of Dubai, Kuwait, Qatar and Tiawan are among the 57 individuals or foundations who reportedly gave $1 million to the Clinton library. President Clinton has refused to make the full list public, citing the need to protect the anonymity of donors.
But to assuage public concern and to insulate Hillary, many say that Bill might have to scale back his efforts with his charitable foundation and presidential libary.
"I think there would have to be both transparency and I don't see how Bill Clinton wouldn' t have to pull back what he's doing," said Melanie Sloan, executive director of Citizens for Ethics and Responsibility in Washington.
Whatever arrangement vetters come up with, Bill Clinton's relationships are likely to linger if Hillary joins the Obama cabinet.
"Changing it from here on out is good and that would amelirotate some concerns," said Ken Boehm, chair of the National Legal and Policy Center. "But it wouldn't undo what already exists."