Accessing the black hole of the CIA

Answer

As an initial matter, you should determine whether or not an Executive Order classifies as confidential CIA employment records (at least those for “operatives” employed at any time during the last 25 years, as the federal government recently announced that documents classified for national security reasons that are more than 25 years old will generally be declassified).  There are cases going back a few years that indicate that the CIA does not have to produce any records that would identify any current or “former” agents at least to the extent it would reveal sources or methods of information gathering or any other classified information (in fact, even former agents who have publicly acknowledged their status as an ex-CIA operative have been unable to use FOIA to get CIA records relating to themselves).

If you get over that hurdle, you would have to convince the CIA (and, perhaps, a judge), that confirming whether the mayor was a CIA operative is not an unwarranted invasion of privacy.  That is because the FOIA exemption for personnel records only applies to information in those records the disclosure of which would constitute a clearly unwarranted invasion of privacy.  There are cases holding that the release of the names of employees of a particular department (including even the Transportation Security Agency) is NOT an unwarranted invasion of privacy, at least where the public has a substantial interest in the information, and other cases holding that the release of names of employees of a particular department (say, for example, the CIA) IS an unwarranted invasion of privacy at least absent a strong public interest in the information.  Compare Gordon v. FBI, 388 F. Sup. 2d 1028 (N.D. Cal. 2005) (ordering FBI to release the names of certain TSA employees) with Davy v. CIA, 357 F. Supp. 2d 76 (D.D.C. 2004) (CIA could withhold names of employees involved in projects related to JFK because disclosure would constitute an unwarranted invasion of their privacy).

Interestingly, in the Davy case the CIA apparently did not claim that the names of its employees were classified by an Executive Order classifying national security material, but only “argue[d] that a privacy interest clearly exists because the withheld information would identify CIA employees.”  357 F. Supp. 2d at 87.

In short, I don’t think it’s a matter of how you word the request.  It’s more a matter of pointing out the public interest in confirming whether the mayor is accurately describing her employment history with the CIA.