Rudy Giuliani’s high-dollar foreign clients could present legal problems: Experts

President Donald Trump's personal attorney Rudy Giuliani, now at the center of a congressional impeachment inquiry targeting the president, once dreamed of securing the top spot at the State Department, only to voluntarily remove himself from the shortlist just after his name started coming up.

But the former New York City mayor’s decision to bow out from consideration for the secretary of state gig wasn't necessarily a missed opportunity.

Since Trump took office, the president's longtime friend, who became his personal lawyer in April 2018, has maintained numerous lucrative business endeavors representing foreign clients around the world and in at least two cases consulting with Trump on the matters.

Although much of his career has been focused on domestic politics, Giuliani has had a long history of consulting work on behalf of a wide range of foreign clients, from a high-level security consulting deal with the Qatari government in 2007 to a $4.3 million security contract with Mexico City.

Most of Giuliani's past foreign work appears to have amounted to consulting for his foreign clients, not necessarily lobbying, according to a review of his work based on publicly available documents and media reports by ABC News, which means that he hasn’t had to register as a foreign agent under the Justice Department.

But some of the more recent foreign interests Giuliani has pursued have at times gained momentum thanks to the president’s support, raising the question about whether his relationship with Trump may have crossed a line when it comes to lobbying.

Experts have said Giuliani's more recent work for his various foreign clients -- often brought up to the president's attention -- could fall under the category of activities that need to be registered and reported under the Foreign Agent Registration Act, also known as FARA.

"It requires registration not just for lobbying, but for any activity that Giuliani intended to or believed might influence the U.S. government or the U.S. public with reference to any political interests of a foreign nation," Josh Rosenstein, a lawyer with expertise in FARA compliance, told ABC News. "So grassroots work, media work, public relations work and speeches all may be covered. Even drafting a lobbying strategy or advising a foreign client on how to best interact with the U.S. government, without actually doing the lobbying for the client, may trigger FARA, unless another exemption applies."

"Whether Mr. Guiliani has a legal obligation to register under FARA depends on a full examination of all the relevant facts, but based on published reports there are certainly sufficient grounds for the Justice Department to take appropriate investigative steps to obtain those facts," said David Laufman, who oversaw the Justice Department's FARA enforcement unit until last year. Laufman is now in private practice, as a partner at law firm Wiggin and Dana.

The obscure World World II-era law overseeing foreign lobbying in the U.S. has historically been seen as a Wild West with low enforcement rates and a gradual decline in disclosures. The law has been brought to public attention in recent years in light of special counsel Robert Mueller's investigation, which landed at least half a dozen foreign lobbying-related cases.

Even so, some of those FARA-related cases brought by the Justice Department have led to acquittals, demonstrating how difficult they can be to prosecute.

As ABC News has previously reported, prosecutors in the Southern District of New York are looking into Giuliani's business ventures, focusing on whether there were any criminal violations of foreign lobbying laws in Giuliani's work with foreign clients, according to sources.

In the past, Giuliani has argued that his foreign work falls outside the net of rules regulated by FARA. Last year, he told The Washington Post, "I don’t represent foreign government in front of the U.S. government. I’ve never registered to lobby."

Giuliani declined to comment for this article. Below is a list of some of his most notable foreign ventures in the past few years:

Ukraine

More than a decade ago, shortly after withdrawing from the 2008 presidential race, Giuliani took on an advisory role with Vitali Klitschko, a former boxer who at the time was running for mayor of Kyiv. The two convened a press conference in Times Square in May 2008, according to press reports at the time, during which Giuliani told Klitschko that Ukraine needs "a leader like you who can deal with corruption, who can deal with reform of government, which is so necessary."

Klitschko lost that race, but won the job when he ran again in 2014. He remains in the post today. After becoming mayor, Klitschko hired Giuliani on a $300,000 contract to advise Kyiv’s local authorities on how to restore order in the capital after the country’s Maidan Revolution, The Wall Street Journal reported.

Klitschko told The Washington Post earlier this month that he never paid Giuliani for his consultations, but the two appear to remain close. Giuliani recently tweeted his support of Klitschko: "The former champion is very much admired and respected in the US."

Giuliani’s other former high-profile client in Ukraine is Pavel Fuks, a real estate developer and oligarch who once had business ties to Trump. Fuks is widely regarded as one of the most influential oligarchs in Russia and Ukraine, with investments in both countries, plus the U.K. and United States.

Fuks was heavily involved in one of Trump’s attempts to build a property in Moscow, though it ultimately fell through, according to Bloomberg. Fuks claims he paid $200,000 to attend the president’s inauguration in 2017, but later filed a lawsuit accusing an associate he says promised to score the VIP tickets of duping him out of the money and never getting him the tickets.

In summer 2017, specialists from Giuliani Security and Safety visited law enforcement officials in Kharkiv -- Fuks’ hometown -- to consult on emergency services, according to two press releases posted on the firm’s website. Giuliani later told Mother Jones that Fuks paid the contract.

"He was [a] sponsor of a preliminary study that my firm did of security and emergency management in Kharkiv and some on advice on a planned Holocaust Memorial," Giuliani told the magazine.

Fuks has spoken highly of Giuliani, describing him as performing lobbying services in several interviews. Fuks called him "a star" in an interview with Bloomberg and described Giuliani’s firm as providing "lobbying services, and they are very strong in security."

Fuks told The New York Times in June, "I would call [Giuliani] the lobbyist for Kharkiv and Ukraine -- this is stated in the contract." Giuliani took issue with Fuks' characterization of him as a lobbyist, arguing to the newspaper that it "makes it sounds like I lobbied the U.S. government, which I never did."

Experts who spoke to ABC News say Giuliani's work for Fuks could have FARA implications depending on what specific work the former New York mayor did.

"I understand from some public reports that Mr Fuks hired Giuliani with the expectation that Giuliani would represent his interests in the U.S.," Rosenstein told ABC News. "If that’s the case, and he served as a political consultant, for example, then FARA might be implicated."

Another lawyer with expertise in FARA, Dan Petalas, told ABC News there is an exception for "bona fide trade or commercial activity," which does not require registration, but added, "Whether the bona fide commercial activity exception applies depends entirely on the precise nature of the particular tasks and transactions Mr. Giuliani engaged in within the U.S. on behalf of the oligarch."

More recently, Giuliani’s efforts on behalf of Trump in Ukraine have become a key aspect of an impeachment inquiry in Congress. Over the past year, Giuliani, in his capacity as Trump’s personal lawyer, met with multiple current and former Ukrainian officials in an effort to advocate for the incoming government in Kyiv to investigate the president’s domestic political rivals.

Giuliani has repeatedly said he is not being compensated for legal work on the president’s behalf, and the White House has deflected all questions about Giuliani to the lawyer himself.

Turkey

In early 2017, Giuliani had repeatedly pushed for the Trump administration to extradite Turkish cleric Fethullah Gulen, a political rival of Turkish President Recep Tayyip Erdogan living in voluntary exile in the United States, two former senior level administration officials with direct knowledge confirmed to ABC News.

Trump's former national security adviser, Michael Flynn, was also involved in a similar influence campaign against Gulen in late 2016, penning an op-ed in The Hill comparing Gulen to Osama bin Laden and urging the U.S. to "adjust our foreign policy to recognize Turkey as a priority." In late 2017, Flynn pleaded guilty to charges including lying to federal authorities about the Turkish lobbying operation.

In the case of Giuliani's anti-Gulen efforts, the former senior officials told ABC News that White House officials stepped in and stopped any action from ever happening. The sources said aides told Giuliani he should tell the Turkish government that if they wanted this individual extradited they should contact the Department of Justice directly, which would evaluate this request.

It's unclear why Giuliani was pursuing extradition of Gulen, but regardless of what was motivating Giuliani's interest, Rosenstein says it would have foreign lobbying implications.

"That work -- even if for a non-governmental foreign client -- is political activity as defined by FARA, and I am hard pressed to see an applicable exemption," Rosentstein told ABC News. "Working for a foreign client, in the interests of a foreign government, in seeking some action from the U.S. government, is FARA-registrable."

Later in 2017, Giuliani pursued a separate interest in Turkey, unsuccessfully pushing to help stop the U.S. prosecution of his client, a Turkish-Iranian gold trader accused of bank fraud, money laundering and helping the Iranian government evade U.S. economic sanctions at the same time as the Turkish government was lobbying for the matter.

The effort to assist the gold trader, Reza Zarrab, went all the way up to the Oval Office, with Trump himself urging then-Secretary of State Rex Tillerson to press the Department of Justice to drop the case, as ABC News has previously reported, according to a source with knowledge of the situation.

Many top level aides, including Tillerson and then-White House chief of staff John Kelly, told the president he could not get involved in the matter, saying it would be interfering in an ongoing criminal investigation.

In some cases of foreign work, Giuliani has said he's exempt from registering because he's been acting as his client's attorney. Petalas acknowledged the exception in FARA registration in cases of lawyers providing legal advice, but added that the exception applies only if the legal services are provided in connection with a judicial or agency proceeding."

Rosenstein agreed.

"The lawyer’s exemption isn’t as broad as [Giuliani] wants to make it out to be," Rosenstein said. "To be exempt as a lawyer, his work would need to be limited to representing the client in an actual criminal or civil proceeding -- stepping out on the courthouse steps to have a press conference isn’t 'legal work' exempt from FARA, nor is government-relations consulting."

Romania

In August 2018, Giuliani wrote a letter to the Romanian president, Klaus Iohannis, criticizing the country’s anti-corruption unit for being overzealous.

The Romanian news outlet Mediafax published Giuliani’s letter, in which he berated "excesses done by the National Anticorruption Agency (DNA) in the name of law enforcement," and called for an amnesty for "those who have been prosecuted and convicted following such excesses."

Giuliani’s letter conflicted with the State Department’s support of Romania’s anti-corruption agency, which the U.S. Embassy and several other Western partners credited with "considerable progress in combatting corruption" in Bucharest. The former U.S. ambassador to Romania, Michael Guest, told ABC News that Giuliani’s letter "clearly cut across U.S. policy."

Guest added that Giuliani’s letter puzzled Romanian officials, too. Giuliani did not say on whose behalf he wrote the letter, and told The Washington Post that he "should have put in the letter that [he’s] not representing the president." But he later told Politico that he had been paid by The Freeh Group, a consulting shop run by former FBI Director Louis Freeh, to send it.

At the time, the Freeh Group had been representing a Romanian businessman, Gabriel Popoviciu, who was sentenced to seven years in prison in August 2017 in a case about a corrupt real estate deal in Bucharest. When Popoviciu was sentenced, Freeh released a statement saying he was "deeply disappointed."

Giuliani’s letter to Iohannis did not name Popoviciu specifically. But the connection to Freeh’s firm suggests Giuliani may have written it in an effort to have Popoviciu granted "amnesty," as the letter notes.

Central and South America

Giuliani has also been active in Central and South America, travelling to multiple countries to advise and meet with his foreign clients. Much of Giuliani's work in the past couple years in the Latin America has focused on security consulting through his firm, Giuliani Security and Safety, none of which suggest any lobbying activity.

In May 2018, for example, Giuliani coordinated an effort for the New York Police Department to train and provide "technical support" Honduran national police, according to his website. In the Dominican Republic, he met with law enforcement officials and made suggestions for how to lower crime rates, and in Brazil, Giuliani met with a mayor in Brazil’s Amazon to develop a plan to reduce crime in the region, according to his company. Giuliani's firm has announced similar security consulting gigs in Uruguay, El Salvador and Chile.

The former New York mayor's work for the Brazilian state of Amazons, in particular, has received mixed reviews across the board, from Gov. Amazonino Mendes praising Giuliani's security plan as having set a "milestone in the country's history of fighting crimes," to Brazilian prosecutors in 2018 launching an investigation into "any irregularities" in the bidding process of the Giuliani's contract, according to a local news report. The status of this inquiry is unclear.

Iran (MEK)

Perhaps Giuliani’s most controversial foreign client has been the Mujahideen-e Khalq (MEK), an Iranian opposition group designated by the State Department in the late 1990s and early 2000s as a foreign terrorist organization. Giuliani’s affiliation with the MEK predates the Trump administration by several years, but reflects the breadth of his foreign connections and could spark renewed interest in his past clients.

In a 1997 press release, the State Department said the MEK "have committed, or pose a significant risk of committing, acts of terrorism that threaten the security of U.S. nationals or the national security, foreign policy, or economy of the United States."

In 2012, the State Department decided to delist the MEK, but noted that in doing so, "the Department does not overlook or forget the MEK’s past acts of terrorism, including its involvement in the killing of U.S. citizens in Iran in the 1970s and an attack on U.S. soil in 1992."

Several press accounts have noted that Giuliani was one of many American political figures of both parties who had spoke at MEK conferences. In a 2016 interview with The New York Times shortly after Trump’s election, Giuliani told the paper he "worked very hard to get [MEK] delisted" as a terrorist group.

During a background briefing with reporters in 2012, a State Department official said the decision to delist MEK as a terrorist group "was not made to appease any group of lobbyists, no matter how famous they are."