Keith Kloor is a writer in New York and adjunct professor of journalism at New York University.

On May 6, 2011, retired Lieutenant Colonel Bill Cowan appeared on Fox News to talk about the withdrawal of American troops from Iraq, which he opposed. At the time, Cowan had been a respected Fox News military analyst for a decade; his combat experience in the Marine Corps and background in special operations made him a favorite of Sean Hannity, Neil Cavuto and other hosts.

Although Cowan was in his 60s, the grizzled Vietnam veteran was no armchair analyst. “Just got back from Jordan,” he announced on the broadcast that day, “where I did meet with some senior Iraqi military people.” Cowan said he went there “to talk about business and what was going on inside Iraq.”


In fact, Cowan went as a covert operator on behalf of the U.S. military, as part of a highly classified program contracted out by the Pentagon. Over the next year, he would make more than a dozen such trips to Iraq and other parts of the Middle East, he told me, as part of a larger black ops portfolio for the Defense Department that began in 2002. That was the same year Fox News signed him to an exclusive contract to talk about terrorism, Islamic militants and, as time wore on, the wars in Afghanistan and Iraq—all areas that intersected with his clandestine activities.

His work for the Pentagon was so secret that only about a half-dozen people in the U.S. government were aware of it. According to Cowan and three former Pentagon officials and associates of his, the Pentagon tasked Cowan with running numerous unacknowledged “special access programs” (SAPs)—secretive assignments that “others couldn’t and wouldn’t do,” Cowan told me; these included, he says, working with the Iranian opposition in 2008 and helping to take down a so-called high-value target in Afghanistan around the same time. “The intel world is complex,” Cowan said to me in one email. “The office I supported had unusual latitude.”

The Pentagon declined to comment about Cowan’s contracts while he was a Fox contributor: “We don’t discuss Special Access Programs with the public,” a duty officer wrote in an email. Cowan says he never told anyone at Fox News about his undercover work for the Pentagon while he was being paid by the network to comment on military matters, which many in the journalism world would consider a conflict of interest. A Fox News spokesperson confirmed that Cowan did not inform the network of his clandestine government work. “Had he done so,” the spokesperson said, “Fox News would not have allowed him to serve as a contributor.”

Other Fox News commentators have had ties to the Pentagon, but national security and intelligence professionals I spoke with said Cowan’s case is unique: It’s odd for someone to work undercover on classified programs for the government while simultaneously being a public figure in the media. “It’s a gamble,” says retired Army Lieutenant General Jerry Boykin, who served as deputy undersecretary of defense for intelligence between 2002 and 2007 and knew of Cowan’s double life when he was at the Pentagon in the 2000s. “If you’re going to get into the world of espionage, you want to stay low profile.”

Now in his mid-70s, Cowan would likely still be pulling off this dual existence if not for a series of personal and professional troubles that beset him several years ago, primarily related to an unmet divorce settlement. The nadir came on September 24, 2015, when two police officers arrested him in front of his youngest daughter’s elementary school, in Leesburg, Virginia, after he had surprised her with a lunch visit. Cowan spent the next 45 days in the Loudoun County Adult Detention Center—he still owed his ex-wife $273,000.

By then, the Defense Department had already severed its relationship with Cowan—he believes it was retaliation for his outspokenness on TV. It’s been a hard fall for the hard-bitten Marine, whose legal and financial woes have mounted since his 2015 arrest. Last year, he was so short on cash that he briefly took a job stocking shelves at a supermarket. Today, there are outstanding warrants for his arrest in South Carolina and Virginia. Cowan says he is currently living in an unfurnished apartment somewhere out West to avoid being arrested again. A man who made his career on risky foreign operations is now carrying out one last mission: living on the lam.

How does someone with Cowan’s chops, who not that long ago was earning well north of six figures as a wily covert operative and popular Fox News pundit, wake up one day to find himself broke and on the run? Even more curious: How does such a highly visible media figure keep his military work secret? “I never let on to anyone, anywhere, that I was involved in some really sensitive stuff,” he told me.

Some of Bill Cowan’s many appearances on Fox News | FoxNews.com

That appears to be true. I have talked with many of his family members, friends and former business associates, plus more than half a dozen others who have served with Cowan in the military dating back to the Vietnam War. I have also spoken to people who worked closely with him in the “black” world, such as Boykin.

How does someone with Cowan’s chops, who not that long ago was earning well north of six figures as a wily covert operative and popular Fox News pundit, wake up one day to find himself broke and on the run?

Although Cowan’s downward spiral is largely a product of his personal life, his story opens a window into the workings of a clandestine world walled off inside the government, known to few and seemingly accountable to none—so much so that a man regularly on TV could do some of the Pentagon’s most covert work.

Then again, maybe there was something strategic about Cowan’s double life. As Boykin explains to me, when Cowan was traveling overseas for clandestine work, his Fox News profile gave him (in tradecraft terms) what is known as “cover for status”—reason for being in a particular foreign land. And if he happened to be spotted meeting with anyone under surveillance, then his Fox status gave him “cover for action.”

Cowan’s advanced age and pleasant demeanor on air at Fox News also “worked to his advantage,” Boykin says: “People looked at him on TV like he was an avuncular uncle, when in fact, he was a steely-eyed killer.”

***

I first became aware of Cowan’s peculiar saga in 2016, shortly after he reached out to me by email, under a pseudonym. He said he had information about a former employer who was refusing to pay him—a Virginia woman named Michele Ballarin, who had cultivated ties to East African politicians, warlords and members of the U.S. intelligence community and whom I had profiled for the Washington Post magazine. Soon enough, Cowan, who sports a white goatee and alternates between a shaved head and a crown of thinning hair, revealed himself; we met twice for lengthy interviews, in Maryland in the spring of 2017 and then a few months later at his home in Myrtle Beach, South Carolina, and spoke many times on the phone thereafter.

Cowan’s career dovetails with some of the most troubled chapters in American military history over the past 50 years, from Vietnam to Iraq. Over the course of that career, as the number of countries where the U.S. military has troops ballooned to some 150, Cowan often found himself in the thick of the fight.

A photo of Bill Cowan at a helipad in Quang Tri City, capital of Vietnam’s northernmost province, in March 1968. “I was waiting to lift off on a CIA operation,” Cowan said. | POLITICO

After graduating from the Naval Academy in 1966, Cowan was shipped to Vietnam—at the height of the war—as a young Marine officer and platoon commander. On his last tour, Cowan spent more than two years in the Rung Sat Special Zone, a 400-square-mile crocodile- and snake-infested mangrove swamp (nicknamed the “forest of assassins”) that the Viet Cong used for staging attacks. There, Cowan collaborated with the CIA in a notorious counterinsurgency initiative dubbed the Phoenix Program, which aimed to root out communist operatives and their supporters who had melted into rural hamlets. One of the program’s main components was the use of “Provincial Reconnaissance Units” (PRUs), local paramilitary militias comprised of Vietnamese soldiers and trained by the U.S. army and CIA. Rampant abuses within these units, including torture and assassinations, became synonymous with the Phoenix Program.

Cowan insists that the PRU unit he ran in the Rung Sat Zone had a purely military objective. “With me, the PRU were focused on enemy elements and base camps in the mangrove,” he says. “Our focus was always prisoners. A prisoner had much more to offer than a body.”

After returning stateside and starting a family, Cowan went where the military directed him, which included an educational stop at the Defense Intelligence College (since renamed the National Intelligence University). In 1983, he was recruited into a super-secret new U.S. Army unit called the Intelligence Support Activity (ISA). The group had been mandated to carry out covert intelligence collection and targeted military operations. Cowan was immediately deployed through the ISA as an undercover operative in Beirut, amid a brutal stretch of Lebanon’s civil war. One of his missions was to help track down those responsible for the truck bombing on the Marine barracks there, which had killed more than 200 U.S. military servicemen. The ISA drew up a plan for retaliatory strikes, but he says top Pentagon brass rejected it.

Disenchanted, Cowan left the unit and the military in 1985. Several years later, he vented about his Beirut experiences to journalist Steven Emerson for his book Secret Warriors: Inside the Covert Military Operations of the Reagan Era. Former ISA members tell me Cowan’s blabbering got him excommunicated from the unit’s fraternity. “Word went out that no one was to have anything to do with Bill,” I was told by one retired ISA agent, who requested anonymity because he still consults for the Pentagon and retains a top-secret clearance. “He couldn’t be trusted.”

Cowan again began a new chapter, as a legislative staffer to Republican Senator Warren Rudman. In 1987, he helped write legislation that established the U.S. Special Operations Command (SOCOM) in Tampa, Florida. Today, special operations are a heralded, core component in the fight against terrorism—think Delta Force or Seal Team Six—but back then, special ops commandos were treated like the military’s bastard children, a threat to the traditionalists. “The Pentagon fought [SOCOM] tooth and nail,” Cowan recalls. “They didn’t think it was necessary.”

Still blackballed by his old special operations comrades—ironically, at a time when he was helping to elevate their standing—Cowan decided to put his black ops skills to use in the private sector. In 1991, William Colby, the ex-CIA director who had also run the Phoenix Program in Vietnam, enlisted Cowan to oversee a private clandestine mission that rescued American businessmen stranded in Kuwait after Saddam Hussein had invaded the country. The operation became the subject of an episode on a Discovery Channel documentary show in which Cowan was interviewed.

Cowan bounced around in the 1990s between Washington and California. By then, his first marriage, of 17 years, had collapsed. He needed a new high-adrenaline outlet and perhaps a new band of brothers. So Cowan tricked out a Harley and joined a motorcycle club for Vietnam veterans. He shaved his head, grew a Fu Manchu mustache and openly embraced his club name, Bezerk, displaying it on his Harley and his car license plates. “All the big clubs were nervous about the Viet Nam Vets,” as the group was known, Cowan proudly says. “They didn’t fuck with us.”





***

Lucky for Cowan, not everyone in the military intelligence community got the memo that he was, as one former member of his old ISA unit put it to me, “persona non grata.” Once George W. Bush’s war on terror commenced, there was a need for crafty old hands like Cowan, who was now nearing 60 and long removed from his last government-sanctioned clandestine mission. Feeling duty-bound to serve his country, he told me, he agreed in 2002 to run a top-secret unacknowledged SAP that the Pentagon was taking over from the CIA.

The U.S. military has authorized SAPs for more than half a century (the ISA itself was born as an SAP). These secretive programs fall into three general categories: weapons or technology acquisition, intelligence collection and tactical support. SAPs are either “acknowledged” (but still classified) or “unacknowledged,” meaning information about them is restricted to only those with an absolute need-to-know clearance. “Program funding is often unacknowledged, classified, or not directly linked to the program,” according to a 2007 Special Access Security Manual.

Cowan wouldn’t tell me exactly what his assigned unacknowledged SAP was designed to do except to emphasize its “national strategic level” importance; he said it is still ongoing without him today. “Disclosure would create an international crisis of sorts,” Cowan says. Boykin told me Cowan had a contract with the Pentagon before Boykin arrived as undersecretary for intelligence in 2002, and that the contract was renewed during his tenure there, which ended in 2007. But he said he couldn’t give me “any specific or operational details about what [Cowan] was contracted to do. … It’s very sensitive.”

As Cowan describes it, his original SAP contract grew into multiple “tasks.” Some of them were actionable covert missions; others died in the planning stage—for example, an operation against Hezbollah, the militant Islamic group that has dominated Lebanon’s political landscape for decades. Cowan says he put together a team of advisers that included former journalists, such as his friend Richard Carlson (father of Tucker), who decades ago was the director of the Voice of America and then president and CEO of the Corporation for Public Broadcasting. “Nothing kinetic,” Cowan says. “All psy-ops and info-ops. Just mess with their heads a little bit, mess with the heads of people supporting them. Get pornographic magazines in their trash, alcoholic bottles, things like that.” Cowan says he also proposed using disinformation techniques, such as planting phony information on Facebook and other social media platforms. The schemes never came to pass, he says, because Pentagon higher-ups “don’t like creative thinking.”

At the Pentagon, there is zero tolerance for those in the know who discuss SAP work publicly, though Cowan seems surprisingly unconcerned. In 2006, a British journalist named Michael Smith published a book about ISA’s history and exploits. Cowan cooperated with the author, and, again, word went out—this time from the highest levels at the Joint Special Operations Command, according to a former ISA operative who served with Cowan, that no one in ISA, past or present, was to have any contact with Cowan.

Yet there he was, working in the black ops world for several more years—while also serving as a paid military analyst for the most watched cable news network in America. After 9/11, the late Roger Ailes, then the chairman and CEO of Fox News, assembled a roster of camera-ready retired military officers. Ailes wanted Fox to ooze muscular gravitas as the Pentagon went after the Taliban in Afghanistan and then Saddam in Iraq. Retired Army Major General Paul Vallely told me he was directed by Ailes to put together the team of military analysts and got a Fox contract for Cowan, who had already appeared on “60 Minutes” and “PBS Frontline.” Cowan distinguished himself at Fox as “a highly regarded go-to guy,” says retired Navy Captain Chuck Nash, another member of the Fox military analyst team at the time.

During this period, many of the military analysts seen on Fox and other networks, including Vallely and Cowan, were granted private Pentagon briefings and access to classified information in the run-up to the Iraq invasion and during the war. It was part of a coordinated Pentagon information campaign to “generate favorable news coverage of the [Bush] administration’s wartime performance,” the New York Times revealed in a blockbuster 2008 story.

In an unpublished, unfinished autobiography Cowan gave me, he writes that his media perch at Fox was a useful front while working secret government programs in the 2000s. “My public persona was in my being a Fox News Channel contributor,” he writes. “My real persona was something else.”

“My public persona was in my being a Fox News Channel contributor,” Cowan wrote in his unpublished autobiography. “My real persona was something else.”

But when I mentioned this dual life to one former ISA agent who had served in Cowan’s unit, the source was incredulous: “I find it a little hard to believe that Bill would be allowed a [security] clearance, let alone working on an SAP, while being such a visible, vocal talking head on Fox.”

“Maybe they [the Pentagon] didn’t care,” says Lucy Dalglish, Dean of the Philip Merrill College of Journalism at the University of Maryland. “The people who knew what he was doing may have been saying, ‘Good for you, buddy, what a great idea.’ I don’t think it is a conflict for them the way it is for journalism.”

Cowan, for his part, doesn’t see any conflict between his black ops work and his frequent appearances on Fox as a paid military analyst. He says he never considered himself a journalist. “I was a commentator,” he asserts. But that distinction doesn’t hold water for Dalglish. “No, if you’re an employee of Fox or any media organization, you have a certain duty to your employer under your contract, and one of those duties is not to essentially lie to them about your other contracted work.”

I tried to explain this to Cowan, but he rationalizes what he did. With the exception of a half-dozen times he accompanied country music singer Aaron Tippin to Iraq for charity events, Cowan says he never flashed his Fox News ID while he was working abroad for the Pentagon. “I went as a businessman. I went as a car salesman,” he says. “I have a briefcase full of Motor Trend and Car and Driver magazines.”

***

Cowan juggled his double life for well over a decade, until a series of events in his secret and private lives collided, with disastrous consequences.

The first big hit came shortly after he and his business partner got the green light from the Pentagon for a new, separate $85 million unacknowledged SAP. Boykin helped facilitate the contract just before he left the Pentagon, Cowan says. (Today, Boykin is executive vice president of the Family Research Council, an influential conservative Christian organization.) At the time, Cowan’s second marriage was collapsing; he would soon be on the hook for a six-figure alimony settlement, as well as child support for three young children.

Bill Cowan holds a gun in a "Newsmakers" segment from a local Fox affiliate. | YouTube

Cowan and his business partner spent six months laying the groundwork for the program, which he told me was designed to gain access to technology in China and Iran. But shortly after Boykin left, in 2007, a new senior Pentagon supervisor took over the program and terminated it, Cowan says. Cowan thinks the supervisor—who could not be reached for comment—was jealous of his Fox position or angry at him from a previous run-in.

In such a furtive, walled-off environment, supervisors of SAP programs have a lot of discretion and little accountability, says John Smith, who was deputy general counsel for intelligence at the Pentagon under Defense Secretary Donald Rumsfeld. There is an SAP oversight committee comprised of a few select officials in the Pentagon who are supposed to meet every six months to review all SAPs. But Smith says that SAP program managers “know that there is little chance, any chance, of them being accountable to someone above them who will say, ‘What is it that you are doing?’”

Despite losing the new $85 million contract, by the time Barack Obama became president in 2009, Cowan still held on to another contract, the SAP he had been working since 2002. Cowan had occasionally dinged President Bush on Fox and conservative radio shows, but he began denigrating Obama frequently on air, and often in biting terms. An associate of Cowan’s became concerned, asked him to dial down his rhetoric and, when that failed, enlisted “some fairly significant people—high-ranking folks” to do the same, the associate told me.

It didn’t work. In the waning months of the 2012 presidential campaign, Cowan and a group of former special operations soldiers and retired spies appeared in a short film called Dishonorable Disclosures, and accused the Obama White House of leaking details about the Osama bin Laden raid for PR purposes. The Obama administration denounced the video, and the central accusations against Obama were quickly refuted by the journalist Peter Bergen and rated “mostly false” by PolitiFact. The video still got attention for a few news cycles, particularly one soundbite near the end of the film from a smirking Cowan, who tells Obama to “shut the fuck up.” Cowan amplified his cutting remarks on Fox News, seeming to revel in the controversy.

According to Cowan, in early fall of 2012, he was handed a pink slip by his program manager, who, like Cowan, was a retired military officer contracted by the Pentagon. Cowan says he was told by this manager that the order came from top Pentagon brass, and that his dismissal stemmed from his harsh public criticism of Obama. Although Boykin had been retired by then, he told me Cowan had “pissed off people in SOCOM with that video.”

“He was bashing the Joint Chiefs of Staff,” added the individual who had tried to get Cowan to dial down his rhetoric. “They got tired of the criticism. It was clearly payback.” (The Pentagon declined to comment.)

The ultra-secret work had been Cowan’s livelihood and the primary source of his income: He had made roughly $300,000 that year from the SAP, he told me, clocking in 12-16 hours a day while on his undercover trips in the Middle East. As his income plummeted over the next several years, he fell behind on alimony payments to his second wife. She sued him, according to Virginia Circuit Court documents, triggering legal proceedings that would not go well for Cowan.

There was one bright spot in his increasingly tumultuous life: He got married again, on New Year’s Eve 2013, to his third wife, Velvet Leigh Shelton; she was 38, and he was 66. They moved to a sumptuous country house on five acres in Mount Airy, North Carolina, Velvet’s home state. She was active in the Tea Party and Republican politics there. Cowan remained in good stead at Fox, taping segments at the local affiliate in Winston-Salem, and he became a popular speaker on the local Tea Party circuit and wrote columns for the Daily Caller, continuing to criticize Obama.

But the media gigs weren’t enough to dig Cowan out of his deepening financial hole. He thought he would find relief in a procurement deal that he says had been in the works for some years, but in 2015, his conduit to Pentagon decision-makers, Richard Hagen, was indicted for a massive fraud scheme and shot himself dead in his New Jersey house. Another lucrative offer, working a vague project in East Africa with Michele Ballarin and her business partner Greg Christos, never materialized. (In an unrelated matter, Christos was arrested by federal agents in November 2017, after being charged with a 23-count indictment that includes money laundering and wire fraud.)

In June 2015, Cowan skipped out on a hearing related to his wife’s lawsuit. He was cited for contempt of court. He went about his life, remaining in contact with his three little girls from his second marriage. (Their mother, Cowan’s ex-wife, declined to comment.)

Then, one day that fall, Cowan paid a surprise visit to his youngest daughter at her Virginia elementary school. Two county deputies were waiting for him.

Cowan spent more than a month in the Loudoun County Adult Detention Center. He was ashamed. “I’ve never been in trouble with the law in my life. I didn’t want to tell anyone I was in jail,” he says.

The night before he was arrested, he had been on Hannity discussing Afghanistan.

***

It was Cowan’s friend Richard Carlson who bailed him out, loaning him $25,000 to make a good-faith payment to his ex-wife. Carlson had visited Cowan in his first week in jail. “We talked through a glass for 10 minutes,” he told me. “It was pretty bizarre.” The two men have grown close over the past decade and collaborated frequently on projects. In 2014, they co-authored a “satirical novel” premised on the kidnapping of Hillary Clinton. Until recently, they also co-hosted a weekly radio show called “Danger Zone.” It was billed as “insider information” on the troubled hot spots of the world.

Cowan’s arrest and incarceration in 2015 didn’t initially sideline him. He went back to making Fox appearances right away and continued to appear at Republican events. (At one South Carolina Tea Party gathering in 2016, Steve Bannon, the Donald Trump aide, introduced Cowan as an “American hero, a great patriot, a colleague and a friend … one of the great warriors in our country.”) At the end of 2016, Fox did not renew his contract; several other retired military analysts have seen their Fox contracts expire in recent years. Last year, a children’s court in Virginia stripped Cowan of all visitation rights to his three daughters. By then, he and Velvet had moved to Myrtle Beach, South Carolina, in search of a fresh start. But his legal woes dogged them.

In July 2017, Cowan emailed me to say another warrant had been issued for his arrest in South Carolina after he had missed the deadline for an agreed-on $104,000 payment to his ex-wife. As of today, Cowan says, he lives in a small city about a two- or three-day drive from his Myrtle Beach home, where his third wife has remained. His Facebook page says he’s in Silver City, New Mexico. In emails to close friends who are familiar with his current situation, Cowan signs off as “fugitive.” He says he spends his days on the phone in a nondescript office, trying to sell cars and heavy equipment overseas. He stays in periodic touch with a small circle of family and friends, including Carlson, who wrote about Cowan’s situation (without ever naming him) for a local paper in South Carolina paper, in an opinion article titled “Courtroom Savagery Worse than the Vietcong.”

The abrupt cancellation of Cowan’s $85 million SAP a decade earlier still eats at him. He believes that money—which was specifically earmarked for his SAP—got diverted to other pet black programs run by friends of the program manager who stripped Cowan of the contract. “It’s waste, fraud and criminal negligence,” he says.

He hoped to convince the Trump White House to do an audit of ultra-classified SAPs, and floated the idea to Rich Higgins, who joined President Trump’s National Security Council in 2017 as a director for strategic planning. But Higgins was fired from the NSC last summer because of a controversial memo he wrote that “globalists,” “Islamists” and the “Deep State” were trying to sabotage Trump.

Carlson and Cowan, however, have a new idea up their sleeves. The two told me they are now shopping around a proposal for a reality television show. Cowan described it to me as “true stories of people using guns to defend themselves,” with the title “The Right Side of Justice.” (They initially called it “Grannies with Guns.”) When I checked in with Carlson about it recently, he told me that a Hollywood producer has expressed interest in the idea.

But Cowan isn’t waiting around for a silver bullet to solve his problems. He seems resigned to his situation. “At some point, I’m going to get arrested and thrown back in jail,” he says. When that happens, Cowan figures he’ll finish the autobiography he started a few years ago, which he has titled Livin’ the Life: A Warrior Story of Excitement, Adventure, and Fox News.