By Keith Kloor

On May 6, 2011, retired Lt. Col 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 sixties, 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 Lt. Gen. 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.

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.

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 …read more

Read more here: The ‘Steely-Eyed Killer’ Who Became a Star on Fox News – Then Lost It All

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