WASHINGTON — 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 Qaeda 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 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. 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.
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 approximately 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.
Flynn is now under scrutiny by the FBI as well as congressional investigators. He declined to comment for this article, and his lawyer, Robert Kelner, declined to answer questions.
‘I learned that following the way you’re supposed to do things isn’t always the way to accomplish a task.’Michael Flynn, in a 2015 interview
Trump, who is spending the weekend at Camp David for the first time, acknowledged before leaving Washington that he is under federal investigation as part of the expanding inquiry into Russia’s election meddling, led by former FBI director Robert S. Mueller.
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.
In fall 2014, Flynn registered his new company, Flynn Intel Group, from an Alexandria, Va., 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 maker Adobe, which paid him a six-figure fee to provide “periodic counsel to Adobe’s public sector team,” according to a company spokeswoman.
As Flynn consulted for US cybersecurity companies, he was developing closer financial ties to Russia, a country whose own intelligence apparatus was moving aggressively to penetrate US 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 US 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.
In December 2015, Flynn traveled to Moscow for a paid speaking engagement on behalf of RT, the Kremlin-financed news network that US 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 Mueller.