Feature

Draft Dodgers

The little Gmail trick that David Petraeus and Paula Broadwell used to communicate is actually old spycraft.

As it turns out, the Gmail trick David Petraeus and his paramour used to hide their correspondence is one commonly employed by CIA field operatives when agency bosses turn down their pleas for more sophisticated gear to communicate with their foreign spies.

According to the Associated Press, the erstwhile CIA director and his biographer girlfriend, Paula Broadwell, shared a Gmail account that allowed them to post private notes they could each read, rather than trade emails that could easily fall into the wrong hands.

And it wasn't just an amateur dodge: the Gmail trick can be safer -- and far cheaper -- than using sophisticated "spy gear," such as encryption software, that might have drawn more scrutiny, intelligence sources say.

The Gmail sharing gambit, former agency operatives note, became a common fallback option when more sophisticated gear was deemed unnecessary or possibly even incriminating if discovered in the hands of a CIA spy.

It was used mostly to communicate with low-level spies who had access to high-level documents, such as the minutes of cabinet meetings or the blueprints for a new fighter jet.

"There are some clandestine assets who mainly provide documents -- they handle memos, plans, reports," and these people don't require frequent personal meetings, says a former deep-cover CIA officer, since "the asset did not attend the meeting where the document was discussed, approved, or knew of the decisions made."

Planting stolen documents under rocks and bridges -- so-called dead drops -- was often too risky. The agency needed better places for their spies to squirrel away the materials until they could be retrieved by their CIA handlers.

Microsoft provided the answer. 

"When laptops and home computers became commonplace, even overseas, then lots of ops officers wanted [to be able to supply] their assets with ‘secure' commo -- laptops or PCs with special software that could hide a scanned copy of a document inside a normal letter or photograph," said the former deep-cover CIA officer about the sensitive espionage tradecraft.

It's called steganography, defined as "the art and science of writing hidden messages in such a way that no one, apart from the sender and intended recipient, suspects the existence of the message." Over the past decade or more, it's been a trick commonly used by terrorists and criminals as well, other CIA veterans say.

But CIA headquarters managers were wary of supplying it to the field. Possession of specialized steganography software would be every bit as incriminating as a radio set during World War Two and the Cold War.

"The agency fought back against the field ops officers on this, because if one asset got compromised, then that particular version of the software would have been assumed to be compromised and have to be removed" from circulation, the former operative continued.

So the field operatives did a work-around, this person said, "by asking their assets to give them their passwords for their work or personal e-mail accounts. Then the asset would write up a phony e-mail and leave it in ‘drafts,' perhaps with a document attached. The ops officer would log on remotely, collect the document, and then debrief the asset about it when they met in person."

But why not use at least some commonly available commercial encryption software, such as PGP (Pretty Good Privacy) to further obscure the messages and documents?

Because a spy -- and above all a spy chief -- would have a hard time explaining why he was using encrypted email out of approved channels.

"Using PGP was also an indication that you were using spy gear," the former operative said. Foreign security services constantly scan email traffic looking for encrypted messages, he said. So does the FBI and NSA, who have the tools to break it.

As for Petraeus, his agency-approved and encrypted message channels are monitored -- he couldn't risk tapping mash notes via those. But he would be trusted not to use his personal email to discuss business. And according to news accounts, no one would have paid attention to his personal accounts had his girlfriend not started sending harassing emails to a perceived rival, who then called a male friend in the FBI.

The shared Gmail account Petraeus and Broadwell used on their home and office computers was good enough to hide evidence of their liaison from coworkers and unsuspecting spouses, another operative points out, but not much else.

"Once law enforcement zeroes in on you, if you're using your home computer, it doesn't matter what technique you use," he said. The origin of the Gmail is the smoking gun.

Allison Joyce/Getty Images

Feature

Covert Affairs

A short history of spies and their sex scandals.

As long as there have been spies, there have been spy scandals. Usually, however, it's because a senior official got hooked up with an enemy spy, most famously like British Secretary of War John Profumo, who in 1963 was "dating" an alleged call girl who was also involved with a Soviet naval official suspected of being a spy. Down he went.

That was a long time ago. And in the half century since, there's no known record of a Western intelligence chief resigning over the love of a person not his wife.

Until Friday, that is, when the once unsinkable David Petraeus announced he was resigning because of his  "extremely poor judgment by engaging in an extramarital affair."

The target of his affection was quickly identified as Paula Broadwell, the author of a recent hagiographic book about him, All In: The Education of General David Petraeus.

According to veteran intelligence reporter Ron Kessler, who has a well-drilled pipeline into the FBI, the resignation of Petraeus "followed an FBI investigation of many months" prompted by the interception of an email he sent to the "girlfriend."

Nothing remotely like that has touched the 19 CIA directors who preceded Petraeus.

The late William Colby, who headed the agency briefly during the tumultuous post-Watergate congressional investigations into assassinations in the mid-1970s, abruptly divorced his wife of 30 years and took up with a younger woman, but that was long after he resigned.

Which is not to say other senior CIA officials haven't been entangled in messy affairs and indiscretions, and easily survived.

A chief of the CIA's operations wing after 9/11 was caught on a security camera in an agency garage getting oral sex from a female subordinate, according to a widely circulated story. It didn't dent his reputation, perhaps because he was poorly regarded anyway, three agency sources said, and already on the way out.

Likewise, one of the CIA's chiefs of station in Baghdad after the 2003 invasion was "notorious for sleeping with subordinates," as one senior ex-agency official put it, in an account echoed by several other sources over the years. "He was put in the penalty box a couple of times," the source said, "but it was never never anything fatal," despite the written complaints of at least one woman serving there. He went on to to other higher-ranking agency jobs.

CIA operatives are supposed to be outliers of a sort, so no one should be surprised. But there's some invisible line that can't be crossed.

"In the [training] class before mine," another former operative recalled Friday, one [trainee] was ejected for dropping his pants in a bar in front of female trainees. He later ran (unsuccessfully) for congress, and actually had the nerve to refer to his CIA background during the campaign, I'm told, confident that the CIA wouldn't comment on why he no longer worked there."

"That one definitely happened," the source said. "They made things tougher on my class because of that moron."

In contrast, lower-level operatives who get entangled in affairs with foreigners often pay a steep price, usually because they failed to report it fully, although men who did the same got off scot-free, according to memoirs by former operatives like Melissa Boyle Mahle.

The problem is that affairs can leave operatives, or officials, open to blackmail. While the KGB had a training program for "swallows," women (and men) deployed to seduce officials and spies in the United States and other western governments, the CIA wasn't adverse to using the technique as well.

Usually, the gambit is employed as subtly as a stiletto: cameras are deployed in hotel rooms to record the target in flagrante. Presented with the evidence, the target either meekly succumbs to blackmail, or if he or she is smart, quickly reports it to superiors and the matter is discreetly deep sixed.

The Russians are still at it, judging by numerous instances, including the 2001 discovery by a British MP that an aide was suspected of being a Moscow spy.

The game is played many ways. In 1941, the FBI discovered that a young Navy lieutenant in Washington, John F. Kennedy, was dating a Danish beauty by the name of Inga Arvad, whom it had under surveillance as a suspected Nazi spy. Kennedy was warned to stay away -- or else.

These days, the CIA's ranks are honeycombed with women, many in senior positions. Since they, like their male counterparts, are recruited in part for their naturally wily ways, which are encouraged by spy training, it's not surprising that some use sex to get ahead.

"I went through training with a very hot young ops officer trainee," recalled another former agency operative Friday, "who slept her way to the top with a COS [chief of station], managed to get stationed with him on Cyprus, and then they both had to resign in disgrace because the COS was trying to buy and smuggle out rare Greek Orthodox Icons via dip pouch. They both got cashiered."

Win some, lose some.

"Then there was the female NOC officer who slept with all of her Brazilian agents to get information on their rocket program and nuclear weapons program," this former operative continued. NOCs -- an acronym for non-official cover, are CIA spies who work outside a U.S. embassy, without benefit diplomatic protection.

"The sex with agents was overlooked because she produced good intelligence. So they promoted her to be the first NOC officer in Moscow. Where she promptly fell in love with an FSB officer named Yuri and moved into his apartment. They never did get back her commo [communications] gear. Then they sent another female NOC officer to Moscow, and didn't tell her about the ‘fate' of the first NOC.  When she found out, she quit the agency and was never heard from again."

Such stories, whispered with glee at agency watering holes along Route 123 in McLean, Va., always seem to be mostly true, but who knows?

Several CIA sources were curious about why Petraeus was forced to resign, rather than just admit to an affair, separate from his wife, and move on.

But those who know him called it "an honor thing" that "violated his personal code."

In any event, these days the CIA's director, like other agency employees, has to submit at some point to a polygraph exam on "lifestyle" questions, which certainly would have prompted a confession to the affair. 

"There's no way he'd make it through without talking about that," said former agency official Charles Faddis. "That's gonna blip."