That’s what the FBI was asking itself in 1988. That year is not a typo. Gawker  has scans of the FBI documents showing that the reputed Godfather of neo-conservatism was a person of interest in an ongoing investigation into a potential Soviet spy.
The FBI heavily redacted the documents—citing national security in many instances—so it’s difficult to make out exactly what happened. But it seems fairly clear that, sometime around May of 1988, the FBI’s counterintelligence division came to possess a notebook or address book belonging to a suspected Soviet agent. And Irving Kristol’s name was in it. That launched a five-month investigation into Kristol’s background, including criminal record checks, interviews with “assets” at the school where he taught, and eventually an interview with Kristol himself, conducted under a “pretext” so as to avoid letting him know the true nature of the investigation. This despite the fact that Kristol had already been subjected to an FBI background check in 1972, when he was considered for a job in the Nixon White House, and came up clean.
Now it would be easy to make too much of these. Soviet spooks could have easily written Kristol’s name in their notebooks to throw investigators off the scent, or just for a few late-Soviet era giggles. Kristol had been strongly identified with anti-communism for a long time by 1988. The FBI report is funny – it includes a section describing the American Enterprise Institute written as if by foreigners. It notes “AEI employment appears to be a viable option to those having already achieved a successful career” before mentioning Robert Bork.
The writer of the FBI report seems to conclude on the basis of a Nexis review that Irving Kristol would naturally be of interest to their suspected Soviet spy, and seems to conclue that Kristol’s denial of ever meeting with him as sufficient evidence to close the investigation. I’m not sure that would qualify even as good journalism, but it sufficed for the FBI. What a fascinating late Cold War era document.
Of course committed conspiracy theorists will make the most of this sort of thing. The John Birch Society still promote the idea that William F. Buckley Jr.’s National Review was a CIA operation aimed at destroying nothing else but the John Birch Society. This one will surely take on a life of its own as well.