The in-depth Vanity Fair profile of the infamous owner of Blackwater, Erik Prince, is remarkable on many levels–not least among them that Prince appeared to give the story’s author, former CIA lawyer Adam Ciralsky, unprecedented access to information about sensitive, classified and lethal operations not only of Prince’s forces, but Prince himself. In the article, Prince is revealed not just as owner of a company that covertly provided contractors to the CIA for drone bombings and targeted assassinations, but as an actual CIA asset himself. While the story appears to be simply a profile of Prince, it might actually be the world’s most famous mercenary’s insurance policy against future criminal prosecution. The term of art for what Prince appears to be doing in the VF interview is graymail: a legal tactic that has been used for years by intelligence operatives or assets who are facing prosecution or fear they soon will be. In short, these operatives or assets threaten to reveal details of sensitive or classified operations in order to ward off indictments or criminal charges, based on the belief that the government would not want these details revealed. “The only reason Prince would do this [interview] is that he feels he is in very serious jeopardy of criminal charges,” says Scott Horton, a prominent national security and military law expert. “He absolutely would not do these things otherwise.”

There is no doubt Prince is in the legal cross-hairs: There are reportedly two separate Grand Juries investigating Blackwater on a range of serious charges, ranging from gun smuggling to extralegal killings; multiple civil lawsuits alleging war crimes and extrajudicial killings; and Congress is investigating the assassination program in which Prince and his company were central players. “Obviously, Prince does know a lot and the government has to realize that once they start prosecuting him,” says Melanie Sloan, a former federal prosecutor and the executive director of Citizens for Responsibility and Ethics in Washington. “In some ways, graymail is what any good defense lawyer would do. This is something that’s in your arsenal.”

Perhaps the most prominent case of graymail was by Oliver North when he and his lawyers used it to force dismissal of the most serious charges against him stemming from his involvement in the Iran-Contra Affair. In another case, known as Khazak-gate, a US businessman, James Giffen, allegedly paid $78 million in bribes to former Khazakh Prime Minister Nurlan Balgimbayev in an attempt to win contracts for western oil companies to develop the Tengiz oil fields in the 1990s. In 1993, he was charged with violating the Foreign Corrupt Practices Act in the largest overseas bribery case in history. After Giffen was indicted, he claimed that if he did what he was accused of, he did it in the service of US intelligence agencies. The case has been in limbo ever since.

“This is as old as the hills as a tactic and it has a long track record of being very effective against the government,” says Horton. “It’s basically a threat to the government that if you prosecute me, I’ll disclose all sorts of national security-sensitive information. The bottom line here is it’s like an act of extortion or a threat: you do X and this is what I’m going to do.” Horton said that the Vanity Fair article was Prince “essentially putting out the warning to the Department of Justice: ‘You prosecute me and all this stuff will be out on the record.'”

According to Ciralsky’s article, Prince was a “full-blown asset” of “the C.I.A.’s National Resources Division [which] recruited Prince in 2004 to join a secret network of American citizens with special skills or unusual access to targets of interest:”

Two sources familiar with the arrangement say that Prince’s handlers obtained provisional operational approval from senior management to recruit Prince and later generated a “201 file,” which would have put him on the agency’s books as a vetted asset. It’s not at all clear who was running whom, since Prince says that, unlike many other assets, he did much of his work on spec, claiming to have used personal funds to road-test the viability of certain operations…

Prince was developing unconventional means of penetrating “hard target” countries–where the C.I.A. has great difficulty working either because there are no stations from which to operate or because local intelligence services have the wherewithal to frustrate the agency’s designs. “I made no money whatsoever off this work,” Prince contends. He is unwilling to specify the exact nature of his forays. “I’m painted as this war profiteer by Congress. Meanwhile I’m paying for all sorts of intelligence activities to support American national security, out of my own pocket.”

“I think that [Prince] will use all of his information and his knowledge of these secret dealings in basically what is an extortion play: ‘You come after me, and I’ll spill the beans on everything,'” says Horton. “That’s the essence of graymail and the Department of Justice will usually get its feathers all ruffled up and they’ll say, ‘You can’t deal with the government like this. This is unfair and improper.’ But in the end, it usually works.”

In the Vanity Fair article, Prince alleges that he was outed–by whom he does not say, but the implication is that CIA Director Leon Panetta named him in a closed door hearing of the Intelligence Committee last June, and then the name was leaked by one of the attendees of that hearing. Sloan, the former federal prosecutor, said that if what Prince says in the Vanity Fair article about his role in secret CIA programs is true, he has a case that laws were broken in revealing his identity. “I’m not his fan, but he’s not wrong. For somebody to leak his identity as a CIA asset clearly merits a criminal investigation,” Sloan said. “Whether they should have ever hired Erik Prince or made him into an asset is a separate question. Assuming he really was a CIA asset, basically a spy, an undercover operative, and somebody decided to leak that, that’s not acceptable and that is a violation of the same law that leaking Valerie [Plame]’s identity was. If you can’t leak one person, you can’t leak any person, not just the people you like versus the people you don’t like.”

While much of the focus in the Vanity Fair story was on Prince’s work with the CIA, the story also confirmed that Blackwater has an ongoing relationship with the US Special Forces, helping plan missions and providing air support. As The Nation reported, Blackwater has for years been working on a classified contract with the Joint Special Operations Command in a drone bombing campaign in Pakistan, as well as planning snatch-and-grab missions and targeted assassinations. Part of what may be happening behind closed doors is that the CIA is, to an extent, cutting Blackwater and Prince off. But, as sources have told The Nation, the company remains a central player in US Special Forces operations in Pakistan and Afghanistan.

Prince’s choice of Adam Ciralsky to tell his story is an interesting one as well. Ciralsky was a CIA lawyer who in 1997 was suspended under suspicion he was having unauthorized contacts with possible Israeli intelligence agents. Ciralsky vehemently denied the allegations, saying he was the victim of a “witch-hunt” at the Agency. In any case, there is no question that Prince would view Ciralsky through the lens of his own struggle against the CIA. “When I saw the article, the first thing that just leapt off the page was his name. I thought, ‘My god, why would he go to Adam?'” said Horton. “And then I read the article and I thought, of course he’d go to Adam. There is this legal theme being developed in the article and Adam, as a lawyer who had dealt with the CIA, fully understands that. I mean I think he fully understood he was going to do a piece that would help Prince develop his legal defense and that’s what this is. The amazing thing to me is that Vanity Fair printed it. Do the editors of Vanity Fair not understand what’s going on here?”