The Alienation of Michael Flynn: From the War on Terror, to Russia, to Trump
This article describes the biography of Michael Flynn, relating how he went from a remarkable career in the US military, to establishing various lucrative connections in Russia and becoming one of Donald Trump’s top political surrogates during the 2016 election.
It is the first part of the series, “Michael Flynn, Information Operations, and the Search of Hillary’s Missing Emails.”
This article is an excerpt from my book, While We Slept: Vladimir Putin, Donald Trump, and the Corruption of American Democracy, available here.
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“Russia, if you’re listening, I hope you are able to find the 30,000 emails that are missing,” intoned the Republican nominee for President. “I think you will probably be rewarded mightily by our press.”
Donald Trump made this statement while speaking in Miami on July 27th, 2016. Five days earlier, Wikileaks had released 20,000 internal DNC emails on the eve of Democratic National Convention.
Russian military intelligence was listening to Trump as he spoke on that balmy Miami day. Within five hours of his making the statement, hackers from the GRU’s Unit 26165 targeted Hillary Clinton’s personal office for the first time.
After calling for Russia to hack Clinton’s email server, Trump turned to his own team to pursue a parallel effort. In particular, he turned to his most vociferous supporter from the US military, the recently retired three star Lieutenant General Michael T. Flynn.
Flynn’s background in intelligence and extensive connections within that murky world, including a remarkable set of connections within Russia itself, made him ideal for the job. After being asked “repeatedly” by Trump to find Hillary’s “missing” 30,000 emails, the mission oriented Lt. General understood his task and pursued it with gusto.
Beyond these efforts Flynn engaged in further activities to aid the Trump candidacy, many of which remain shrouded in mystery.
The story of how Flynn went from a legendary military career serving in Iraq and Afghanistan to supporting the Russian-backed, insurgent candidacy of Donald J Trump sheds light on the wider Trump phenomenon.
Michael Thomas Flynn was one of nine siblings born to a middle class, Irish-American Catholic family in Middleton, Rhode Island.
His father had enjoyed a distinguished military career during the Second World War fighting with General George S. Patton during the Battle of the Bulge. Flynn’s mother was a noted lawyer and activist for the Rhode Island Democratic Party.
Despite his respectable parentage, by his own description Flynn “was one of those nasty tough kids, hell-bent on breaking rules for the adrenaline rush and hardwired just enough to not care about the consequences.”
In The Field Of Fight, part-memoir, part-political call to arms, Flynn describes engaging in “some serious and unlawful activity” as a youth. He dropped out of college, leaving his freshman year with a 1.2 GPA.
His life turned around upon joining the military and becoming an Army intelligence officer.
Flynn joined the 82nd Airborne Division and first deployed during the 1983 US invasion of Grenada. He later played a role planning the 1994 American invasion of Haiti.
It was during the wars Iraq and Afghanistan that Flynn distinguished himself. In particular, he made his mark in Iraq as a colonel in charge of intelligence gathering and analysis at the Joint Special Operations Command (JSOC), a counterterrorism unit composed of SEALs, Rangers and Delta Force special operators.
At the time, Iraq was consumed by a violent insurgency.
Flynn realized that while JSOC was excellent at taking individuals off the battlefield, it was failing to adopt a comprehensive strategy aimed at neutralizing wider terrorist networks.
Under the leadership of General Stanley McChrystal, Flynn played a central role in organizing reciprocal relationships between JSOC and its traditional rivals in the CIA, NSA and FBI.
He further revolutionized the military’s interrogation process, expanding the use of digital technology and information sharing that led to a dynamic intelligence gathering process that was followed up by near immediate special forces operations designed to disrupt networks and kill or capture insurgents and then repeat the process.
Flynn’s experiences in Iraq left a lasting impression on him.
He spent hours interrogating members of the Sunni Islamist group Al-Qaeda in Iraq, then led by the bloodthirsty Jihadist Abu Musab al-Zarqawi.
At one point, JSOC managed to capture 12 high-level members of the group and Flynn was shocked by their high levels of educational and professional attainment and the overall sophistication of the terror group’s leadership and operations.
The question that plagued him was why these intelligent individuals dedicated their lives not simply to fighting the American occupying forces, but to the wholesale slaughter of Shia Iraqis.
“Over the course of all those interrogations,” Flynn said in a later interview, “I concluded that ‘core al-qaeda’ wasn’t actually comprised of human beings, but rather it was an ideology with a particular version of Islam at it’s center. More than a religion, this ideology encompasses a political belief system, because its adherents want to rule things — whether it’s a village, a region or an entire ‘caliphate.’ And to achieve that goal, they are willing to use extreme violence. The religious nature of that threat makes it very hard for Americans to come to grips with.”
Flynn was later involved in the mission to take out Zarqawi, watching a video feed of his safe house being destroyed by an F-16 and later inspecting his charred corpse.
In 2009 Flynn followed Stanley McChrystal to Afghanistan where the latter had been made theater commander.
McChrystal and his allies at the Pentagon were at loggerheads with the newly elected President Obama, who was skeptical of escalating the eight year old conflict. Flynn and McChrystal advocated surging forces as had been done in Iraq.
The Obama White House came to believe that his generals were attempting to box him in after a 60-day assessment of the Afghan War’s progress made by McChrystal arguing that the war was being lost and that the number of forces should be increased was leaked to the press. Obama hedged his bets, agreeing to a surge but with an 18 month withdrawal timeline.
It was the first disagreement Flynn had with his commander and chief, but far from the last.
As Director of Intelligence of the International Security Assistance Force in Afghanistan, Flynn oversaw an assessment of intelligence efforts in the country. The US military, Flynn argued, was focussing on meaningless metrics such as body counts while at the same time neglecting to gain fundamental understanding of the social and cultural currents impacting Afghanistan and its people.
According to Flynn, the solution to this problem could be found in the new and emerging field of “Big Data.”
The military, Flynn wrote, was in possession of a “vast and under-appreciated body of information” that if properly utilized could provide “a map for leveraging popular support and marginalizing the insurgency.”
Roughly concurrent with Flynn’s arrival in Afghanistan, the US Defense Advanced Research Projects Agency (DARPA) implemented a series of Big Data programs in the country. The initiative consisted of a comprehensive data mining effort vacuuming up vast amounts of information on everything from satellite photos to basic economic measures.
The program had two purposes: 1.) to predict insurgent attacks, and 2.) to take advantage of the emerging science of social networks to use the connections between Afghan civilians to gain crucial insights for the American military.
The program designed to predict insurgent attacks was known as Nexus 7. Press reports described Flynn as a “godfather” of the program.
According to Fast Company, it was in this timeframe that SCL Group, the parent company to Cambridge Analytica, came to Flynn’s attention, when it began applying its analysis on the Afghan population under his auspices.
Flynn’s views of Obama further deteriorated after the latter fired General McChrystal following an article in Rolling Stone in which McChrystal was quoted speaking disparagingly of several Obama administration officials, including Vice President Joe Biden.
In 2011, Flynn moved to Washington, DC where he worked at the Office of the Director of National Intelligence (ODNI) under the Obama-appointed James Clapper.
Despite the fact that Flynn’s disdain of the sitting President continued to harden, Obama nominated him to become the 18th Director of the Defense Intelligence Agency (DIA) and he officially took command in July of 2012.
Flynn began his tenure with lofty ambitions. He hoped to increase the number of DIA clandestine human intelligence operatives abroad.
Drawing from his experience in Afghanistan, Flynn also attempted to modernize DIA’s utilization of big data and analytics in order to place it on the vanguard of a larger effort by the US Intelligence Community to standardize its computing infrastructure.
Despite these initiatives, Flynn’s tenure at DIA started off rocky. Unlike JSOC, DIA was a sprawling Washington bureaucracy that required a different managerial skill set that Flynn had difficulty adjusting to.
His colleagues noticed that Flynn was making strange and unsubstantiated claims using what some within the agency began referring to dismissively as “Flynn Facts.”
Beyond getting basic facts and figures wrong, Flynn’s critics at DIA accused him of engaging in politically motivated, speculative, or even in some cases outright conspiratorial thinking that aligned with his preconceived notions.
One of the more controversial actions Flynn took was to become the first DIA Director to visit the Aquarium, as the headquarters of the GRU is known, located at Khodinka Airfield near Moscow.
Flynn was invited by Russia’s chief of military intelligence Major General Igor Sergun. Sergun, who died in mysterious circumstances in early 2016, was described by insiders as a highly capable leader who deftly navigated relations with Vladimir Putin.
The Russian Ambassador to the US, Sergei Kislyak, helped arrange the trip.
Flynn’s visit to GRU headquarters occurred in the context of several other discreet meetings over the period of 2012/2013 between American and Russian intelligence officials that took place in Russian cities such as Khabarovsk, Rostov and Sochi to discuss matters salient to the deteriorating relationship between the two countries.
The high profile nature of Flynn’s visit set it apart and made it controversial among American intelligence officials.
Flynn, who claimed to be aware of Russian efforts to manipulate joint counterterrorism efforts in the past, none-the-less persisted in his desire to foster increased collaboration between Russia and the United States when it came to fighting Islamic extremism.
“He wanted to build a relationship with his counterparts in the G.R.U., which seemed, at best, quaint and naïve,” Steven L. Hall, the CIA’s then-chief of Russia operations, told The New Yorker. “Every time we have tried to have some sort of meaningful coöperation with the Russians, it’s almost always been manipulated and turned back against us.”
James Clapper, who had been asked to visit the GRU’s headquarters after he had retired as DIA director in 1995 but declined the invitation, warned Flynn over the trip.
“One time I had a little chat with him,” Clapper later said, “sort of for some fatherly advice, to ‘just be careful.’”
Flynn arrived in Moscow in June of 2013 and laid a wreath at Russia’s Tomb of the Unknown Soldier before being shuttled to the GRU’s headquarters where he gave a presentation on leadership and intelligence before a gathering of young GRU officers.
According to the American Senior Defense Official and Attache to the Russian Federation Peter Zwack, who was in attendance, the young officers asked questions that indicated they had never met an American intelligence official before.
One can only wonder if any of the other young GRU officers who would play a role in the 2016 election were in attendance.
Read my article about the GRU’s hack-and-leak operations during the 2016 US presidential election here.
Later that evening, Sergun and two other GRU officials dined with Flynn and Zwack at the US Embassy in Moscow. They made several toasts, though Sergun drank only modestly. The final toast called for Russia and the United States to “make the airlocks fit,” in a reference to the linking of the American Apollo and Russian Soyuz famous orbital link-up in 1975.
Flynn left Russia believing he had established a level of rapport with Sergun. Within months, the GRU’s cyber warriors were busily at work supporting Russia’s illegal annexation of Crimea.
Upon returning to the US, Flynn wanted to return the favor and invite Sergun to Washington. After Crimea, James Clapper nixed the idea.
Eventually Clapper and the Under Secretary of Defense for Intelligence Michael Vickers decided that Flynn wasn’t up to the task of managing a large Federal bureaucracy like the DIA and informed him that he wouldn’t be serving out the customary three years but rather would be forced into retirement after only two.
Clapper later suggested that Flynn became “an angry man” after his removal from office.
“I think the termination ate at him,” Clapper told NBC News.
Flynn interpreted events differently. He believed that he had been silenced by an administration that did not want to hear the truth about the threat of Islamic terrorism.
During his retirement speech, Flynn stated bluntly that the US was less safe from Islamist terror than it was before the 9/11 attacks and described himself as a “lone voice” in the administration arguing the point.
“This administration,” Flynn later wrote in The Field Of Fight, “has forbidden us to describe our enemies properly and clearly: they are Radical Islamists.”
He continued a bit further on, “In 2014, I was fired as the director of the Defense Intelligence Agency after telling a congressional committee that we were not as safe as we had been a few years back.”
Michael Flynn Travels to Moscow, Meets Vladimir Putin and Joins the Trump Campaign
In October of 2014, the DIA sent Flynn a letter outlining the restrictions the Emoluments Clause of the Constitution placed on him barring receiving payments from foreign governments without proper approval.
That same month, he established a consulting firm called Flynn Intel Group and registered it in the Alexandria, VA home of Stanley McChrystal.
His first clients included a Silicon Valley firm Palo Alto Networks and the software company Adobe.
Flynn also joined the board of GreenZone Systems, owned by an Iranian-American named Bijan R. Kian (aka Bijan Rafiekian).
Eventually, Kian and a former Army intelligence officer and friend of Flynn’s named Philip Oakley formed a rebranded Flynn Intel Group, now registered in Delaware, and marketed themselves as an elite private intelligence and cybersecurity firm.
In January of 2015, Flynn signed a contract with Leading Authorities, a speaker’s bureau which marketed him as an authority on terrorism, leadership skills and cyber issues.
By the Summer of 2015, in remarkably close succession, Flynn began to be courted by various interests connected to Russia and by the newly launched Trump campaign.
On July 31st, Flynn was paid $11,250 by an American subsidiary of the Russian cyber security firm Kaspersky Lab to make a speech. The company’s founder, Eugene Kaspersky, was educated at the High School of the KGB, where he studied cryptography. Kaspersky then served as a Soviet intelligence officer before founding his cyber security company.
Emails seen by Bloomberg establish that Kaspersky Lab has developed software for the FSB and even accompanied its agents on raids. Kaspersky’s chief legal officer, Igor Checkunov, is a former KGB officer.
Court documents leaked online indicate that Kaspersky Lab has cooperated with the FSB and that FSB agents have visited their Moscow office.
The US Government later banned Federal agencies from using Kaspersky software over fears of Russian espionage, though the company has denied these charges.
Nor was Kaspersky Lab the only Russian company that paid Flynn.
That same day, July 31st, Flynn was paid an $11,250 by a Russian charter airline company called Volga-Dnepr Airlines to make a speech at an event in Washington, DC.
In 2007, Volga-Dnepr was found to have been involved in an illegal kickback scheme involving a United Nations procurement officer. The UN ultimately suspended the company as a vendor.
In May of 2015, two months before Flynn received payment, the Pentagon deemed the airline “[u]nsuitable for use.”
Less than a month later, Flynn received his first outreach from the Trump campaign. On August 17th, an as-yet unidentified individual (their name is redacted from the materials released by the Department of Justice) put Flynn in contact with Steve Bannon.
As editor of Breitbart, Bannon, though not at that point working in an official capacity for the campaign, was close with its leadership. Bannon connected Flynn with Trump’s campaign manager Corey Lewandowski.
Flynn traveled to New York to meet with Trump. While only scheduled to meet for thirty minutes, they spoke for ninety. Flynn left the meeting enraptured by Trump.
“I knew he was going to be the President of the United States,” he later recalled to The New Yorker.
In early September of 2015, Flynn corresponded with Steve Bannon and Erik Prince, the infamous founder of the mercenary outfit Blackwater, conservative activist, and enthusiastic Trump suppporter.
As he had with Flynn, Bannon had connected Prince with Lewandowski and the Trump team. He then arranged for Prince to speak with Flynn, a fellow soldier and hardline Iran hawk.
Flynn and Prince discussed how the US could work with Russia on issues such as Libya, where Prince had significant mercenary interests. Both believed that the Russians were moving into areas of the Middle East that had been vacated by the US.
Flynn and Prince also discussed the United Arab Emirates (UAE), which they believed had been helpful in Afghanistan.
When later asked by the FBI if he and Prince had discussed a potential back channel to Russia through the UAE, Flynn replied that he “did not remember any such discussion.”
Flynn also recalled that Prince had “carte blanche” at Trump Tower and he often saw him there speaking with Steve Bannon and Jared Kushner.
After its investigation, the Senate Intelligence Committee wrote to DOJ requesting an investigation into Bannon and claiming that he may have lied about his interactions with Eric Prince.
On October 5th, Flynn appeared on RT and attacked the US strategy being pursued against the Islamic State terror group as incoherent, arguing that the US and Russia should confront the group together.
Following the broadcast, a Washington, DC-based representative from RT contacted Flynn’s son, Michael G. Flynn Jr., who served as his father’s chief of staff, and discussed the possibility of Flynn speaking before RT’s Tenth Anniversary celebration soon-to-be held in Moscow.
The RT representative told Flynn Jr. that she had “discussed with, [the] General an opportunity for him to visit Moscow this coming December as a guest of honor of RT’s conference that will mark the 10th anniversary of our news broadcast” and that he “looked very interested in it and asked me to check with you [on] his plans for December.”
After some negotiation regarding his speaking fees, which Alina Mikhaleva of RT suggested was “a bit too high,” Flynn agreed to speak at the event for $45,000, which would be routed to him through his speakers bureau.
Following the signing of the contract with RT on November 11th, the total amount of money paid to him from Russian sources over the course of 2015 approached $70,000.
RT also offered to pay for business class travel to Moscow for Flynn and his son and to put them up at the Metropole, a luxurious five-star historic hotel in the heart of the Russian capital.
Flynn used the opportunity to promote yet another of his business interests. He had been providing consulting services for a nuclear energy company called ACU Strategic Partners, which was planning to put together a group of US, European, Arab and Russian companies to build as many as 40 nuclear reactors across the Middle East.
In June of 2015 ACU changed its name to IP3 and toyed with various configurations of the companies involved, some of which excluded Russia.
That same month, Flynn traveled with IP3 co-founder Admiral Michael Hewitt to the Middle East to discuss a plan with officials from Egypt, Jordan and Israel.
On November 28th, 2015, three days before RT announced Flynn’s speaking engagement, he wrote to Hewitt that he would be willing to “relay any messages to specific people” while he was in Moscow.
He further explained that he was planning an “office call with RU AMBO [Russian Ambassador] before we depart.”
Shortly thereafter, in an email that cc’d Flynn and was sent on December 8th, the day Flynn arrived in Moscow, IP3’s General Counsel Alan Dunn described how he had just met with the Saudi Ambassador to the United States and explained “how the architecture of the project is intended to align Saudi, US and Russian interests on many important issues for the 80 year life of the project.”
Prior to leaving for Moscow, Flynn and his son met with Ambassador Sergei Kislyak at his residence for a mid-afternoon courtesy call.
Flynn also received a courtesy classified briefing on Russia from DIA. Agency officials later claimed that Flynn failed to disclose all the relevant details as to the nature and purpose of his trip.
Flynn stayed in Moscow from December 8th-11th, 2015. On the evening of the gala, he was seated at the head table directly next to Vladimir Putin.
Others seated around them included the former KGB agent Sergei Ivanov, Putin’s then chief-of-staff and fellow classmate at the Red Banner Institute, Kremlin spokesman Dmitry Peskov, RT Editor-in-Chief Margarita Simonyan, and Jill Stein, the Green Party candidate for the upcoming US presidential election.
When photos of Flynn sitting next to Putin became public, Greg Miller reports that Flynn’s replacement at DIA was so angry he had the agency change the rules around providing classified briefings to retired members.
During the conference, Flynn was interviewed by RT. While stating that Russia’s ally in Syria, Bashar al-Assad, was not the future of the country, Flynn argued that Russia and the United States had shared interests in fighting the Islamic State.
Other speakers at the event included Julian Assange, who was beamed in via telecast from the Ecuadorian Embassy in London.
At some point during his trip, Flynn met with the CIA’s station chief in Moscow and lectured him about Russian-American relations, suggesting that the US needed to “ease back.”
When Flynn asked for a follow-up meeting the next day the station chief refused, worried that Flynn had met with Russian officials in the interim and either had un-asked for suggestions, or possibly even information he wanted to collect.
Nine days after he returned from Moscow, Flynn wrote to Trump campaign chief Corey Lewandowski on December 19th. Attached to his email was an article from Sputnik, another Russian-state backed news organization, entitled US Must Cooperate With Russia, Arabs to Defeat ISIL.
In the article Flynn argues for increased US and Russian cooperation in Syria. Flynn wrote to Lewandowski that this was “something Mr. Trump should at least be aware of… I have been very outspoken on this issue.”
Flynn continued, “I met with President Putin last Thursday in Moscow. We actually sat at dinner together.
As 2015 passed into 2016 and the presidential election started to heat up, Flynn became an ever more prominent and vocal Trump supporter.
In February, he appeared on CNN and called for Hillary Clinton to drop out of the presidential race.
“If it were me,” Flynn told CNN news anchor Jake Tapper in reference to the Clinton State Department email saga, “I would have been out the door and probably in jail.”
Flynn further attacked Clinton for a “lack of accountability, frankly, in a person who should have been much more responsible in her actions as the secretary of state of the United States of America.”
At the same time, Flynn’s social media statements were becoming more strident. “Fear of Muslims is RATIONAL,” he wrote on Twitter at the end of February.
Shortly thereafter, he retweeted a picture of refugees streaming into Europe and featured text that read, “Historians will look back in amazement that the West destroyed its own civilization.”
On March 20th, Flynn emailed Trump campaign policy advisor Sam Clovis, copying Corey Lewandowski. “Below is a recent OPED from Russian Foreign Minister [Sergey] Lavrov,” Flynn wrote. “I strongly recommend Trump read this.”
Lavrov’s op-ed was a long and ponderous meditation on Russian history and its unique role in global affairs that blamed the current poor state of Western relations with Russia on the expansion of NATO. Flynn then suggested that Trump arrange to meet and speak with Henry Kissenger.
“Regarding Russia, Flynn continued, “we lack any serious strategic thinking in our current administration — they see Russia as an enemy — as long as we do that, nothing good will come of it. We have to directly confront Russia and take collective steps to figure out how we are going to deal with them going forward. We don’t need to be friends, but we need to start somewhere — and there are good and valid starting points that do exist.”