David Petraeus, Hillary Clinton and the Perils of Email

They screwed up—just like the rest of us. Jason Reed/Reuters

The New York Times's scoop that Hillary Clinton used her personal email account for her digital correspondence as Secretary of State has a lot to do with David Petraeus's plea deal for leaking classified material. Both concern the perils of the modern age.

Clinton may or may not have broken federal regulations when she blew off her official email account and instead used one from her domain, "clintonemail.com." Clinton's office said she hewed to the letter and spirit of the law regarding federal archives, but experts quoted in the piece expressed doubt that what Clinton did—hand-culling her personal emails and deciding which ones were official and archivable—was in keeping with the statute. Either way, it looks at least for now more like a case of, at most, misinterpreting regulations than violating the law.

In Petraeus's case, there's no doubt that he broke the law. He admitted it as part of a plea deal. At issue was his sharing of secrets with a woman who would become his mistress. In his position as a military commander and director of the CIA, Petraeus's very location was often classified, meaning that quotidian notes such as "I'm in Omaha" were as classified as "I told the president this morning..." Either way, Petraeus was impossibly reckless not only in his choice of words but in his lover as well. Had Paula Broadwell, his paramour, not lobbed angry emails at a Tampa socialite, Jill Kelley, whom she considered to be too close to Petraeus, none of this might have come to light. Kelley took her complaints to the FBI,and the investigation was born. If it were a movie, there would have been gunplay. Instead we have the smoking gun of gmail.

Alas, Petraeus and Clinton are not alone when it comes to tripping over work and personal email. Virtually anyone in a white-collar job has both a personal email account and a work one and few people practice the kind of rigid hygiene required to keep them apart. You use work email to say you'll be late for dinner, and a private one to tell your boss the project is over budget. Either way, I'd be hard-pressed to think of anyone who is hypercautious about which to use—even though the consequences are considerable. Your company could go after you for taking sensitive information out of its system. Put personal things in your company email, say about your health, and who knows where that could end up?

Efforts to avoid getting caught usually fail. Petraeus and Broadwell made some efforts to avoid detection. Instead of corresponding between two email accounts they each logged into the same account, creating drafts for each other. But Broadwell corresponded with that account from her own, leading investigators to Petraeus's disclosures.

As for Clinton, I've never heard of anyone in government completely blowing off their government email to use their personal email for everything. I've written to government officials I know on their personal and business accounts and sometimes the messages have gotten crossed. Most have been pretty judicious about their use. I served on a government commission in 2009 and 2010 and I remember being quite mindful about what went where—even if one occasionally cringed at the thought that some historian would eyeball one's catty comments.

We're about 25 years into the era of widespread email use. You would think by now people would have learned the basics about deletion, keeping things offline, etc. On the other hand, 50,000 years of evolution never quite prepared us for the day when our exact thoughts could be captured and distributed instantly. People forget about discretion when they're sitting in a cubicle farm. Little surprise then that while David Petraeus may have been the soldier of his generation but in the adrenaline rush of war, and the endorphin swelling rush of a love affair, he was reckless with his email in a way that he never would be with his sidearm. For Clinton, it's hard to understand why, if she and her staff believed her email use to be legal, she would not have gotten an opinion saying as much. After all this is pretty unusual. Given the scrutiny that she's always under for opacity, why she and her staff wouldn't have been more careful is puzzling. Then again, you can never go wrong betting that smart people will make the most obvious mistakes—especially when it comes to email.