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Behind the email trail that brought down General Petraeus

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On November 9th, David Petraeus stepped down as Director of the Central Intelligence Agency, after an FBI investigation revealed an affair with biographer Paula Broadwell. His departure was sudden, and while an official resigning over infidelity didn’t break any new ground, the investigation was far more unusual. Initial reports said that the FBI had believed someone else to be accessing Petraeus’ personal Gmail account and began monitoring it, uncovering the affair in the process. Some questions have been resolved as more details emerged, but the surrounding story remains murky, touching on security issues, petty rivalries, and the risks of communicating through "anonymous" channels that are ultimately anything but.

Why was the FBI monitoring Petraeus' email? Well, it may not have been

One of the biggest initial questions was why the FBI had been checking Petraeus’ email at all. It’s now believed he wasn’t the original target, and it’s not even clear that he was being monitored. The bureau was actually investigating anonymous threats to Jill Kelley, a Tampa woman who helped organize military social events at the base where US Central Command is located. Petraeus ran Central Command from 2008 to 2010, and Kelley said in a statement that she had known him and his family for over five years.

The Associated Press and The Wall Street Journal report that Kelley contacted the FBI about "five to ten" anonymous emails that started in May. While their exact contents is still unknown, some reportedly accused Kelley of having or contemplating an affair, and they were apparently enough to launch an investigation. According to The New York Times, it didn’t hurt that Kelley was also friends with an FBI agent, who was able to kickstart the process.

The threats, the FBI soon deduced, were from Petraeus biographer Broadwell

The emails, the FBI soon deduced, were from Broadwell. While she had created a throwaway address, the bureau was able to connect her by matching email metadata (likely IP addresses) to hotels and other locations that Broadwell had stayed. Once the bureau suspected she was to blame, The Wall Street Journal reports, it obtained a warrant to monitor her email, starting with an account she shared with her husband — and soon after, it found a separate Gmail account with sexually explicit messages between her and someone who appeared to be Petraeus.

The FBI apparently believed someone had hacked Petraeus’ personal account or was posing as him

At first, the FBI apparently believed someone else had hacked Petraeus’ personal account or was posing as him to send the emails, a suspicion that was hinted at in the first reports. It’s unknown whether this led them to monitor his email too, or whether they looked for other ways to check the messages’ veracity. Either way, when investigators determined that they had found an affair between Petraeus and Broadwell, it raised other fears. Besides creating a scandal, an affair can leave officials open to blackmail, something that’s especially pertinent when discussing the director of the CIA. In either late September or mid-October, depending on the source, the FBI quietly called Broadwell in for an interview.

When Broadwell was brought in, she confessed the relationship and turned over her computer, adding another layer of intrigue: it contained classified documents that the FBI suspected came from Petraeus. A probe that started with some harassing emails had, it seemed, stumbled onto a serious security breach. Though the exact timeline isn’t known, the bureau seems to have kept quiet after finding the documents, continuing its investigation and asking for a meeting with Petraeus. But Petraeus — who admitted to the affair — denied giving Broadwell the documents, and in early November, Broadwell said they had come from elsewhere.

"Speaking as a friend, colleague and fellow general officer, Gen. Clapper urged Gen. Petraeus to step down."

At this point, the bureau seems to have decided that Petraeus and Broadwell’s affair, which had ended in early summer, posed no security risk. The probe’s conclusions were reported to Director of National Intelligence James Clapper on November 6th — Election Day. By then, however, the news had already leaked. House majority leader Eric Cantor (R-VA) says that a "whistleblower" contacted him in late October through Representative Dave Reichart (R-WA), "concerned that sensitive, classified information may have been compromised." According to The New York Times, it was the same agent who had started the investigation, frustrated by what he saw as stalling progress in the case.

It’s not clear what difference — if any — the leak made on Petraeus’ decision to resign. But a spokesman for General James Clapper says Clapper had asked him to do so on the 6th: "Speaking as a friend, colleague and fellow general officer, Gen. Clapper urged Gen. Petraeus to step down." Afterwards, Clapper notified White House officials, who told Obama on Thursday morning. Petraeus offered his resignation later that day, and Obama accepted it on Friday. Petraeus’ statement to friends and colleagues would be widely reported soon after.

A long-standing departmental rivalry? Technological incompetence? A conspiracy?

Some details may always be missing from the story, but what’s been perhaps most confusing is trying to figure out just what kind of story it is. Is Petraeus’ resignation the result of a long-standing rivalry between the FBI and CIA? Another case of an official being undone by technological incompetence? Was it announced late to give Obama a better shot at the election, or rushed to stop Petraeus from testifying at a hearing regarding the Libya consulate attacks? All these stories have been circulated, and they’re all — as far as we know — wrong.

The FBI / CIA rivalry, former Justice Department inspector general Glenn Fine told The New York Times, "might have been true 20 years ago. But it is hard to believe that is going on today." The connection between Benghazi or the election is also tenuous. An October speech in which Broadwell claimed that the CIA had captured Libyan militia members before the attack has been reported as evidence of a leak from Petraeus, but the anecdote could easily be a garbled version of an earlier Fox News report. It would also have been surprising if this had not come up in the FBI’s report; in fact, the speech was given during the investigation, and the CIA has called the claim "baseless." The election and hearings were almost certainly on the minds of Petraeus and others, but there’s no reason to believe the timing wasn’t coincidental.

A compromised email account bringing down the CIA director would be poetic, but it's not what happened

The idea of a compromised email account bringing down the director of the CIA would certainly be poetic, but reports suggest that if anyone failed to grasp the nature of the internet, it was Broadwell. Without her alleged attempts to threaten Kelley, her Gmail account likely would never have been discovered. Enhanced security wouldn’t have helped Petraeus either, if the affair came out through Broadwell’s email. And it’s possible that the entire situation would have gone unnoticed had Kelley not been friends with a member of the FBI — email harassment, after all, is fairly common.

Petraeus could have encrypted his messages or maintained a false name (he reportedly created the Gmail account under a pseudonym), but the truth is that when everything is connected, it’s difficult to be really unknown. The FBI stumbled across evidence of the affair while tracking Broadwell over at least three email accounts, only one of which had an incriminating connection to Petraeus. Last month, ordinary citizens on Reddit grappled with the implications of matching a real face to an online identity. Now, some of the most secretive parts of the US government are doing the same.

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