Former White House chief of staff Rahm Emanuel used his private Gmail account to communicate with Attorney General Eric Holder during his time in the White House, according to the results of Freedom of Information Act request we filed. Though the Department of Justice has acknowledged just one email exchange with Holder using Emanuel's unofficial address, the disclosure raises questions about whether Emanuel may have sought to skirt the Presidential Records Act by conducting government business using Gmail rather than his White House address. (Or not. See the update below.)

Emanuel, you may recall, was one of the many victims of the massive iPad data leak that disclosed the private email addresses of tens of thousands of movers and shakers in June 2010. Having been privy to his Gmail address, last year we filed requests under the Freedom of Information Act with a variety of federal agencies looking to see if he ever used it to talk to Administration officials—a tactic that the Bush White House perfected as a way to keep email communications off the historical record and out of the hands of prying congressional investigators.

And according to the Justice Department, Emanuel did just that—but only once, and allegedly for personal reasons. "We located one document, totaling one page, consisting of a personal record of Attorney General Holder," the DOJ wrote in response to our request for emails from Emanuel's Gmail address. "Specifically, the document consists of an e-mail exchange concerning a purely personal matter." The DOJ contends that, since the exchange is a "personal record" of Holder's, it isn't subject to the FOIA and refused to release it.

Using private addresses in the White House can be a big no-no. When Karl Rove and other Bushies were caught routinely using accounts supplied by the Republican National Committee to conduct the people's business, it sparked a congressional inquiry. In May 2010, the White House reprimanded deputy chief technology officer Andrew McLaughlin for using his Gmail account for official communications. The Presidential Records Act requires all White House records to be systematically preserved and archived, so using private addresses can introduce huge gaps into the system and violate the law—unless the users conscientiously forward all such emails to their official accounts.

Beyond records laws, doing government business on a personal email account raises security concerns. The iPad breach exposed Emanuel's Gmail handle, a necessary first step toward a targeted hack. The username is not public, and the security group that exposed the iPad security hole said they shared their data, including Emanuel's username, only with Gawker. But the handle could have leaked from AT&T's servers at any point between the device's April 2010 launch and the breach being fixed two months later. The security group, Goatse Security, shared the script behind their iPad exploit with third parties prior to AT&T plugging the leak, as we originally reported, and believed it likely the breach went far beyond their own collection of data. When we asked AT&T last year if anyone other than Goatse had accessed exposed iPad data, the company's flacks, who had been sending us statements, fell silent.

Normally, this might be an academic concern. A username is a necessary but not sufficient component of an account compromise. But this past June, Google disclosed that Chinese hackers had obtained Gmail passwords and silently reconfigured accounts to surreptitiously forward copies of all incoming email to another address. The victims included "senior U.S. government officials," Google added. It's not clear when the compromise occurred, but Chinese hacker attacks on Gmail went back to at least April 2009, and by January 2010 were so bad that Google began pulling out of the country. It's conceivable that Emanuel was swept up in the Gmail hacks.

As for the value of his inbox, there's only evidence so far of one off-label Emanuel-Holder exchange, and it very well may have been innocuous. (We're appealing the DOJ's claim that it's a "personal record.") But given the scrutiny that the Bush Administration received for its email hijinks, and the ongoing pressure the Obama White House has been under from Oversight and Government Reform Committee Chairman Rep. Darrell Issa to account for its use of Gmail and other unofficial communication systems, it seems unlikely that Emanuel would simply carelessly lapse into a Gmail account he never used to send a single email Holder. It is more likely that he regularly used the Gmail account and either scrupulously maintained a distinction between work- and play-related messages, or exclusively sent messages to Holder and other officials' Gmail accounts (and slipped up this one time), which would have kept them out of the ambit of the FOIA. Either way, the contents of that Gmail account might be of intense interest to, say, the congressional investigators currently looking into the Solyndra loan.

We sent requests to the State, Treasury, Homeland Security, Health and Human Services, and Justice departments, as well as the CIA. So far, only Justice has come up with a hit on Emanuel's Gmail; the CIA has yet to respond.

Neither the White House, the Justice Department, nor Emanuel's office responded to requests for comment.

UPDATE: On Friday, November 18, four days after I first contacted them and three days after this item was published, the White House responded to my inquiry. "The e-mail that you identified was sent January 21, 2011, which is several months after Emanuel left the Administration," a senior administration official said via email. That date came as a surprise to me because, as you see from the Department of Justice's response letter above, I sent my initial request on November 16, 2010—two months before the email in question was sent. In my experience, FOIA requests are understood to be backward-looking—agencies explicitly refuse to search for documents that may be created after you file your request. I don't know why the Department of Justice did so in this case. In any event, Emanuel left office on October 1, 2010. Based on my understanding that the Department of Justice was searching for records created prior to my November 16, 2010 request, that left a six-week window when Emanuel could have emailed Holder from his Gmail account after leaving office—a possibility I should have noted in the item. Since the Department of Justice obviously searched for emails after that date, that left a full year after Emanuel left office.