Michael Flynn was a man seething and thwarted. In summer 2014, after repeatedly clashing with other Obama administration officials over his management of the Defense Intelligence Agency — and what he saw as his unheeded warnings about the rising power of Islamic militants — Flynn was fired, bringing his military career to an abrupt end.
Flynn decided that the military’s loss would be his gain: He would parlay his contacts, his disdain for conventional bureaucracy, and his intelligence career battling al-Qaida into a lucrative business advising cybersecurity firms and other government contractors. Over the next two years he would sign on as a consultant to nearly two dozen companies, while carving out a niche as a sought-after author and speaker — and ultimately becoming a top adviser to President Donald Trump.
“I’ve always had that entrepreneurial spirit,” Flynn said in an interview in October 2015. In the military, he added, “I learned that following the way you’re supposed to do things isn’t always the way to accomplish a task.”
But instead of lofting him into the upper ranks of Beltway bandits, where some other top soldiers have landed, his foray into consulting has become a legal and political quagmire, driven by the same disdain for boundaries that once propelled his rise in the military. His business ties are the subject of a broad inquiry by a special counsel investigating Russian interference in the 2016 election and possible collusion with Trump associates. That investigation now includes work Flynn did for Russian clients and for a Turkish businessman with ties to that country’s president, Recep Tayyip Erdogan.
Flynn sometimes seemed to be trying to achieve through business what he could not accomplish in government. He believed the United States was engaged in a “world war” against Islamic militants, and that Washington’s national security elite had so thoroughly politicized the country’s intelligence agencies that few left in government could see the threat. The United States, he believed, needed to take a tougher line against the Islamic State, and it needed to cultivate Russia as an ally in the fight.
“He got out of the service and had a passion to reform the intelligence community, where he saw some deficiencies,” said Todd Wilcox, a former Green Beret and CIA officer who founded Patriot Capital, a Florida-based defense contractor that named Flynn to an advisory board in 2015.
But Flynn also became entangled with controversial clients. One company that paid him, OSY Technologies, is part of a cyberweapons company whose software has been used to hack Mexican activists and an opposition leader in the Middle East. Another, a Boston company selling a technology to replace lie detectors, is accused by its former chief scientist of marketing a counterfeit version of his technology to foreign clients.
Dozens of interviews and a review of public documents suggest that Flynn’s business was as scattershot as it was ambitious — and that there were few opportunities he would pass up. His clients ranged from a drone manufacturer in Florida to major software companies; at one point, Flynn took a $5,000 gig as an expert witness in a personal injury case. Some of his clients came through a tight-knit circle of Iranian-Americans, one of whom became a key partner in Flynn’s businesses.
Flynn’s work paid well — while it lasted. Financial disclosure forms released in March showed income of between $1.37 million and $1.47 million for a period that roughly covered 2016, the bulk of it from the Flynn Intel Group.
Flynn closed the Flynn Intel Group at the end of 2016, as he planned to join the Trump administration. But within months, he was fired as Trump’s national security adviser; the White House has said he was forced out for misleading Vice President Mike Pence about the nature of conversations he had with the Russian ambassador to the United States. Now under scrutiny by the FBI and congressional investigators, Flynn faces legal bills that are well into the six figures, and former clients are scrambling to distance themselves from the ex-general whose counsel they once avidly sought.
Flynn declined to comment for this article, and his lawyer, Robert Kelner, declined to answer questions from The New York Times. But in an interview not long ago, Flynn expressed pride in his moneymaking skills. “I’m a capitalist at heart,” Flynn said in October. “If I’ve discovered anything, it’s that I’m a good businessman.”
A new consulting business
In fall 2014, Flynn registered his new company, Flynn Intel Group, from an Alexandria, Virginia, town house owned by Stanley A. McChrystal, a friend and fellow general-turned-consultant. Among his first clients was Palo Alto Networks, a rising Silicon Valley firm seeking to win more government contracts. A few months later, he inked a deal with software giant Adobe, which paid him a six-figure fee to provide “periodic counsel to Adobe’s public sector team,” according to a company spokeswoman.
But Flynn also joined the board of a little-known company called GreenZone Systems, which marketed secure mobile communications systems. GreenZone was run by Bijan R. Kian, an Iranian-American businessman who served until 2011 as a director of the U.S. Export-Import Bank. A friend of Kian, the businessman Nasser Kazeminy, also hired Flynn as an adviser.
Flynn and Kian soon found a third partner: Philip Oakley, a former Army intelligence analyst, longtime Flynn friend, and owner of two small companies that provided software for defense and intelligence clients. They restarted Flynn Intel Group in June 2015, according to Delaware corporate records, pitching themselves as a premier private intelligence and cybersecurity advisory firm.
None of the partners responded to repeated attempts to contact them. But their business interests were closely intermingled. Beginning in 2015, Oakley’s firms employed Flynn as an adviser and paid him $90,000 in salary over 11 months.
Links to Russian firms
Yet even as Flynn consulted for U.S. cybersecurity companies, he was developing closer financial ties to Russia, a country whose own intelligence apparatus was moving aggressively to penetrate U.S. government systems. In 2015, Flynn accepted a payment from Kaspersky Lab, a Russian research firm that works to uncover Western government spyware and whose founder has long been suspected of having ties to Russian intelligence services.
In 2015, the firm’s U.S. subsidiary, Kaspersky Government Security Solutions Inc., paid him $11,250. The same year, Flynn received the same amount from Volga-Dnepr Airlines, a Russian carrier that has been examined by the United Nations for bribery.
Both payments were for unspecified “services” provided by Flynn, according to a letter sent to the White House in March by Rep. Elijah E. Cummings of Maryland, the top Democrat on the House Oversight Committee, which is examining Flynn’s financial dealings. Kaspersky has said that Flynn was paid for remarks he delivered at a 2015 cybersecurity forum in Washington.
In December 2015, Flynn traveled to Moscow for a paid speaking engagement on behalf of RT, the Kremlin-financed news network that U.S. intelligence agencies say is a Russian propaganda outlet. RT paid Flynn $45,000 for the trip, which also included an invitation to a lavish anniversary party for the network, where he was photographed sitting at the elbow of President Vladimir Putin.
The three payments from Russian companies are among the issues being investigated by Robert S. Mueller III, the special counsel leading the Justice Department inquiry.
A growing list of clients
By early 2016, Flynn’s public profile was rising. He had signed a book deal and began hitting the public speaking circuit. The rise of the Islamic State in Iraq and Syria seemed to validate his criticism of Obama administration policy, and Flynn soon become a regular adviser to Trump’s insurgent presidential campaign.
But behind the scenes, his client list was also expanding.
That May, Flynn joined the advisory board of OSY Technologies, part of the NSO Group, a secretive cyberweapons dealer founded by former Israeli intelligence officials. He also consulted with Francisco Partners, a U.S. private equity firm that controls NSO Group.
The same year, the company’s products were linked to an attempt to hack the cellphone of Ahmed Mansoor, a human rights activist in the United Arab Emirates. They were also used to harass public health advocates of a Mexican soda tax, who began receiving threatening text messages.
In a statement, NSO said it “only develops the software, and is not involved in any way, shape or form in operating the system.”
Steve Eisner, the general counsel of Francisco Partners, suggested that Flynn had served the company in a relatively limited advisory role.
“We routinely engage consultants to help us understand industries that we are investing in,” Eisner said. Flynn was paid a little more than $40,000 by OSY, and “less than $100,000” by Francisco, Eisner said.
A slapdash effort
By fall 2016, Flynn was spending significant time on the campaign trail with Trump. Back in Washington, Kian brought in a new client: A prominent Turkish businessman named Ekim Alptekin, who headed a Turkish trade association with ties to the country’s government.
Alptekin had come to know Kian during Kian’s days at the Export-Import Bank, Alptekin said in an interview this month. Last fall, after the failed July 2016 coup against the Turkish president, he wanted to fight back against those whom Erdogan blamed for the attempt: members of the Islamic religious movement led by Fethullah Gulen, a Turkish cleric who has lived in Pennsylvania since 1999.
“Like many Americans rolling up their sleeves in 9/11 to do something, I decided to do something,” Alptekin said.
His public explanations for hiring the Flynn Intel Group have not always been consistent: In March, he told a reporter that Flynn had been hired “to produce geopolitical analysis on Turkey and the region” for an Israeli energy company.
Alptekin now says that he wanted to hire a credible U.S. firm to lead a public-relations campaign against the Gulenists. Kian suggested the Flynn Intel Group, Alptekin said — though without disclosing his own involvement with the firm.
“You need independent work; you need research that is done by Americans,” Alptekin said. “Flynn was well credentialed; he was a head of DIA.”
The Flynn Intel Group promised what sounded like a sophisticated research and lobbying effort, employing former intelligence and military veterans, and led by Flynn himself. The company would produce a documentary and seek to persuade members of Congress that Gulen ought to be extradited. Alptekin agreed to pay $600,000 for the work.
But the effort appears to have been slapdash from the start, according to several people involved in the effort, who asked for anonymity because of the continuing federal investigations.
Flynn had little to say during meetings, though he would hand out signed copies of his book at each one. A former U.S. intelligence operative named Mike Boston appeared to be quarterbacking the assignment, but according to one person involved, he mostly sat in the corner or paced around the room saying nothing.