I liked this bit from Megan McArdle on Elena Kagan because it fit so well with a category of people I saw all the time at Princeton (Kagan and I overlapped somewhat though I did not know her).
But I do think that David Brooks is onto something when he notes that her relentless careerism, her pitch-perfect blandness, are a little creepy. Not in themselves, but because they're a symptom of a culture that increasingly values what Brooks calls Organization Kids: the driven, hyperachieving spawn of the Ivy League meritocracy who began practicing Supreme Court nomination acceptances and CEO profile photo poses long before they took notice of the opposite sex.
The discussion of late is whether these Ivy Leaguers really are representative of the broader country, but I would add that these folks really were not liked even within Princeton. A great example is Eliot Spitzer. His treatment of Princeton and its student government as a sort of minor league tryout for future political ambitions drove everyone nuts, to the point that he even triggered an outlandish opposition party, the Antarctic Liberation Front.
Back when I was an undergrad at Princeton, one of my fondest memories was of a bizarre Student Body Governing Council (USG) election. The previous USG administration, headed by none other than fellow Princetonian Eliot Spitzer, had so irritated the student body that, for the first time in memory, the usually apathetic voting population who generally couldn't care less who their class president was actually produced an energetic opposition party. Even in his formative years, Spitzer was expert in using his office to generate publicity, in this case frequent mentions in the student newspaper that finally drove several students over the edge.The result was the incredibly funny and entertaining Antarctic Liberation Front. I wish I had saved their brochures, but their proposals included things like imposing a dawn to dusk curfew on the school and funding school parties by annexing the mineral rights between the double yellow lines of the US highways. All of this was under the banner of starting jihad to free Antarctica. The ALF swept the USG election. This immensely annoyed Spitzer and other USG stalwarts, who decried the trivialization of such an august body. The pained and pompous wailing from the traditional student council weenies (sounding actually a lot like liberals after the last presidential election) only amused the general student population even further. After a few student-council-meetings-as-performance-art, the ALF resigned en mass and life went back to being just a little bit more boring.
(Don't miss Virginia Postrel's take on the whole episode, occasioned by Spitzer whining about the episode 20 years later in the New Yorker.)
One other data point: Two years later, after drinking a few adult beverages, it came into my head that it would be a really good idea to moon the USG meeting being held nearby. I asked for volunteers, expecting a handful, and got over 40. The episode saddens me only because I did not think of it soon enough to have mooned Spitzer.