The Obama Administration’s Litany of Email Scandals

President Barack Obama and his administration have long embraced modern technology. He’s the first sitting president to use a BlackBerry and is active on social media; he’s even used a selfie stick. This love of technology has been contagious, with the chairman of the Joint Chiefs of Staff, Gen. Martin Dempsey, now reading classified briefings on his iPad each morning.

But technology hasn’t always embraced the Obama administration back. Here are five examples of high-tech creating old-fashioned political problems for senior officials.

1. Hillary Clinton

The alleged crime: Clinton used a private email account as secretary of state, not an @state.gov address. Emails were routed through a server at her family’s Chappaqua, New York, home.

The charges: Republicans are up in arms, alleging that Clinton was able to hide emails connected to their investigation of a 2011 attack on an American outpost in Benghazi, Libya. The House Select Committee on Benghazi subpoenaed Clintonmail.com Wednesday afternoon. “The American people have a right to a full accounting of all the former secretary’s emails, and the committee is committed to working to uncover all the facts,” Jamal D. Ware, communications director for the Select Committee on Benghazi, said in a statement Wednesday.

The outcome: This is a fresh scandal, but given the GOP’s bloodlust over finding wrongdoing on Clinton’s connection to the Benghazi attack, it’s unlikely to be resolved soon.

2. Lois Lerner

The alleged crime: The Internal Revenue Service could not recover two years of emails from Lois Lerner, the former chief of the agency’s tax-exempt status department.

The charges: Republicans accuse the IRS of politically motivated targeting of conservative groups that opposed the president. “This kind of thing fuels the deep concerns many people have about political targeting by the IRS and by officials at the highest levels,” Sen. Chuck Grassley (R-Iowa) said in a June 2014 statement.

The outcome: Lerner, who refused to answer questions about the missing emails, retired in September 2013 and Republicans, incensed, held her in contempt of Congress. In May 2013, the IRS apologized for targeting groups with “tea party” or “patriot” in their names. An Internal Revenue Service watchdog found 30,000 of her missing emails in November 2014 and is now investigating whether to file criminal charges over their disappearance.

3. Lisa Jackson

The alleged crime: The former Environmental Protection Agency chief created a fake email account in the name of Richard Windsor, a name she stole from a family dog.

The charges: The EPA said she created the account so that certain emails wouldn’t get buried under the 1.5 million messages she received in 2012. The agency called it a common practice but Republicans insisted that she used the identity to dodge congressional oversight. “If those Richard Windsor e-mails weren’t produced during a FOIA request for Jackson’s emails, then that certainly goes against the spirit and intent of FOIA,” Rep. Darrell Issa (R-Calif.) wrote in a January 2013 letter to Jackson.

The outcome: Jackson resigned from the EPA in December 2012 — a few weeks before Issa sent the letter. She’s landed on her feet, taking a job with Apple.

4. Gen. David Petraeus

The charges: Petraeus, who won widespread acclaim for turning around the Iraq war and for heading the CIA, was craftier than most: He and his mistress, Paula Broadwell, shared “intimate messages” in a drafts folder of a shared Gmail account, eliminating a metadata trail.

The alleged crime: However, he wasn’t so shrewd when he emailed her the old-fashioned way, agreeing to share classified black books, which he turned over to her a day after the message was sent.

The outcome: Petraeus resigned as CIA chief in 2013 and pleaded guilty Tuesday to giving highly classified journals to Broadwell, a deal that appears to allow the more embarrassing details about his affair to stay under wraps.

5. Gen. John Allen

The charges: The former top U.S. commander in Afghanistan was collateral damage from the Broadwell affair. Petraeus’s mistress sent anonymous nasty emails to Jill Kelley, a Tampa socialite friendly with military brass who in turn passed them on to a friend in the FBI, prompting the probe which ultimately felled Petraeus.

The alleged crime: In total, Allen and Kelley exchanged a blizzard of emails between 2010 and 2012 that, when all the strings of the messages were printed, took up between 20,000 and 30,000 pages. The content of those emails is largely still under wraps. Some Defense officials initially said they contained “racy” and “flirtatious” conversations, although Pentagon inspectors later said the emails were not so inappropriate that he would be penalized.

The outcome: Allen retired in 2013, shortly after the FBI’s investigation began. He is now the president’s special envoy to the global coalition to fight the Islamic state.

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