Update (2020-11-16): Craig Shirley has taken us full circle now. As described in detail in the Wikipedia article’s Talk page, his online bio at CraigShirley.com has now restored the claim that he “…was also a decorated contract agent for the CIA”, and now cites the Wikipedia article as the source! The citation is stale, of course, sicne the Wikipedia reference was long ago removed as it cited only Craig Shirley’s own bio as its source. I just now asked the Internet Archive’s Wayback Machine to snapshot his site’s bio page, so we can track any future developments in Craig Shirley’s past.
Update (2015-08-26): The claim of CIA employment has since been restored to Craig Shirley’s Wikipedia page, this time with a citation pointing to… craigshirley.com itself as the source! I discuss this in more detail in the Wikipedia Talk page for the Craig Shirley article. (That link is to a specific version of the Talk page, in case it later gets edited and the material I wrote is removed for some reason.)
Last week I wrote about how historian Rick Perlstein had been falsely accused of plagiarism by author Craig Shirley. In the course of writing that post, I looked at Craig Shirley’s Wikipedia page, and found something really surprising. At that time, the page contained this — completely unsourced — assertion about Craig Shirley:
He was a decorated contract agent for the Central Intelligence Agency.
“Whuh?” I thought to myself.
Before going on, I want to make something very clear:
Just because an assertion is on a person’s Wikipedia page, that doesn’t mean a) that the assertion is true, nor does it mean b) that the person who is the subject of the page added it. In other words, Craig Shirley himself might have nothing to do with this claim, and there is no proof here either that he is ex-CIA or that he wanted people to think he was.
Since the claim was unsourced, I added a standard  tag to it (in this change, for those keeping score at home).
A couple of hours later, an automated Wikipedia maintenance bot came along and added a date to my tag. Then a day later, John Broughton, a pretty experienced Wikipedian, came along and removed the claim entirely, on the grounds that contentious assertions must be sourced, and if they are not, the proper remedy is to simply remove them. (John Broughton was quite right, by the way; I’d been tempted to make that edit myself, before settling on just marking it as needing a citation.)
Naturally, I became curious about when and how the CIA claim had first appeared on the page, so I looked deeper into the page history. It turns out it’s been there since 29 December 2012, when it was added as part of a bunch of changes to the page by a user named Reagan1988. Here are all the substantive changes added in that revision by Reagan1988:
His books have been hailed as the definitive works on the Gipper’s campaigns of 1976 and 1980. He is a member of the Board of Governors of the Reagan Ranch and has lectured at the Reagan Library. …
Shirley is the founder of the Ft. Hunt Youth Lacrosse Program, was coach there for 14 years, compiling a record of 121 wins, 19 losses and 4 ties, winning several championships. In the 20 plus years since Shirley founded the program, thousands of boys and girls have enjoyed learning and playing for Ft. Hunt. He was also an editor of Coaching Youth Lacrosse, published by the Lacrosse Foundation.
… His varied interests include sailing, waterskiing, sport shooting, renovating buildings, and scuba diving. He was a decorated contract agent for the Central Intelligence Agency.
This is so embarrassing that I think there’s a real possibility it’s a false-flag operation, by someone who doesn’t like Craig Shirley, to make it look as though Shirley had made these edits to his own Wikipedia page. On the other hand, the CIA assertion stayed in the page from late 2012 until last week. I don’t know Craig Shirley personally, but my guess is that a person who runs a public relations firm is aware of what his own Wikipedia page says, and unlikely to be so concerned about maintaining good Wikipedia form  that he would have let an error remain in his own page for more than a year without doing something about it.
So that’s where things stand. I don’t know how seriously to take the claim that he was a “decorated contract agent” for the CIA, and I don’t know if Craig Shirley had anything to do with its presence in his Wikipedia page.
I wonder who the user “Reagan1988” is. Whoever they are, all they’ve ever done (at least while logged in as that user) is edit Craig Shirley’s page, for a short period between 29 December 2011 and 10 January 2012. They have apparently made no edits since then.
: There isn’t a hard-and-fast rule against editing one’s own page, by the way, though if one can say that one has never done it it’s a nice way to shut down certain trolling arguments. For example, my own page has had an uncorrected error for a few months now. I didn’t put it there, but I also haven’t corrected it since I feel it would be bad form to edit my own page. What Wikipedia’s Conflict-of-Interest Policy says on this is:
If you have a personal connection to a topic or person, you are advised to refrain from editing those articles directly, from adding related advertising links, links to personal websites and similar, and to provide full disclosure of the connection if you comment about the article on talk pages or in other discussions.
An exception to editing an article about yourself or someone you know is made if the article contains defamation or a serious error that needs to be corrected quickly. If you do make such an edit, follow it up with an email to WP:OTRS, Wikipedia’s volunteer response team, or ask for help on WP:BLPN, our noticeboard for articles about living persons.
: Thanks to my friend Sumana Harihareswara for clueing me in to the link for getting all of Reagan1988’s contribution history on Wikipedia.