Rudy Giuliani has a new client: the controversial Turkish gold dealer accused of working around the U.S. sanctions against Iran.

This isn’t the first time America’s mayor has represented a high-profile foreigner or a foreign government.

In fact, since leaving City Hall at the end of 2001, Giuliani and his companies have advised a number of questionable clients.

Qatar dealings

Long before he criticize Hillary Clinton for her relationships with other countries, Giuliani came under fire in late 2007 when the then-Presidential candidate’s ties to Qatar were brought into question.

His firms had security contracts with the country’s government. Those were overseen by the Qatari interior minister, who was accused of sheltering 9/11 mastermind Khalid Shaikh Mohammed. The minister was believed to have given the terrorist the heads up in 1996 when U.S. authorities went to arrest him.

Giuliani, who eventually dropped out of the race, said on NBC’s “Meet the Press” in December 2007 that Qatar was an ally who should keep a good relationship with the U.S.

“We need to develop friendships with the Emirates, we need to develop friendships with Qatar, with Kuwait,” he said at the time. “These are countries that we have to get closer to — we should trade more with them, we should be involved more with them as we stand up to Islamic terrorism.”

Singapore Snafu

Qatar wasn’t the only hot-button issue for Giuliani in 2007.

That same year, he traveled to Singapore as an adviser of a Las Vegas businessman looking to build a casino in the country.

But one of the partners was a Hong Kong tycoon linked to an international crime web, as well as North Korea, according to a 2007 Chicago Tribune report.

Giuliani — a former prosecutor who gained a tough-on-crime reputation as mayor — said his company wasn’t associated with the controversial billionaire.

Iran speech

Giuliani was one of several prominent U.S. officials paid by a group of Iranian exiles to give a speech in their favor.

The Mujahedin e-Khalq, also known as the People's Holy Warriors, paid Giuliani tens of thousands of dollars to give the speech in 2011, according to the Wall Street Journal.

The organization, which at one point was allied with Saddam Hussein, was at the time trying to get off the State Department’s terrorist list.

“We shouldn’t just de-list the MeK; we should applaud them,” Guiliani said. “We should join with them. We’re on the same side.”

Lots of gas

The law firm co-founded by Giuliani served as a high-priced lobbyist for Citgo Petroleum Corp. — the stateside subsidiary of the state-owned Venezuelan gas company.

Giuliani’s firm made about $150,000 lobbying for the company between 2005 and 2006, CNN reported in 2007. It was poised to make another $100,000 that year.

Hugo Chavez, the late Venezuelan dictator, was no fan of the U.S., however, calling then-President George W. Bush a “madman.”

Leadership, Russian style

And Giuliani has showered praise on Russian President Vladimir Putin — the longtime leader accused of punishing his opponents.

Giuliani — who penned a book titled “Leadership” — told Fox News’ Neil Cavuto in March 2014 that he considered Putin a strong leader.

Putin, he said, “makes a decision and he executes it, quickly. And then everybody reacts. That’s what you call a leader.”

Russia at the time was in the process of annexing Crimea from the Ukraine as tensions between the two countries reached a boiling point.