If your interpretation is correct, I don't think the jester analogy holds, since it is the jester who acts/looks absurd.

No I think you just don't understand what a jester is. In the literate tradition (mostly Shakespearean), the fool is a character of uncommon wit that illuminates the ridiculousness of the system around him. While the joke may sometimes appear to be on the fool, the real joke is on his subject. In this way, Jon Stewart is probably the closest we have to a modern jester.

The character that simply looks and acts ridiculous for the amusement of others (your definition) is properly called a buffoon.

I doubt that was the author's intended definition. His article does not seem to be an attempt to distance himself from the sort of behavior your definition of a jester would commit.

Now you're just being obtuse. The author's intent is abundantly clear even if you didn't understand the allusion.

I'm not intending to be obtuse. Even after a second reading, I still don't think the description you give quite matches Drew's use of the term. In his description, wikileaks is being brash and causing trouble, not just shining a light on absurdity through wit. Further, wikileaks is not using any wit, simply publishing everything verbatim.

If Drew hopes to be taken seriously by the US Government and keeping his security clearance (probably highly valuable in his career path) he can't exactly cheer about Wikileaks. This sort of measured, slightly negative review is essentially a bow to power (and there seems like little reason for him to write such an article other than to bow conspicuously before authority).

Drew is also a Homeland Security Fellow, whatever that is.