In The American Scholar, William Deresiewicz writes 

The
world that produced John Kerry and George Bush is indeed giving us our
next generation of leaders. The kid who’s loading up on AP courses
junior year or editing three campus publications while double-majoring,
the kid whom everyone wants at their college or law school but no one
wants in their classroom, the kid who doesn’t have a minute to breathe,
let alone think, will soon be running a corporation or an institution
or a government. She will have many achievements but little experience,
great success but no vision. The disadvantage of an elite education is
that it’s given us the elite we have, and the elite we’re going to have.

He writes that elites who have been funneled through these Ivy League schools are not exposed to normal people and freeze up when forced to have a conversation with a normal people. They are so accustomed to success that they fear taking risks or experimenting. Once they make it through the test preps, honors classes, student government nonsense in high school, they coast through colleges that give them chance after chance. 

I grew up in a town that was a feeder for Ivy League schools. The top 20% of my high school class attended Ivy League schools — some because of merit, some because of family pedigree. My best friend got into Harvard early admission, despite her best intentions of sabotaging her parent’s pressure to attend the family school. Instead of writing the college admission essay, she drew a lovely cartoon of astronauts jumping in and out of craters on the moon carrying flags with question marks on it. A Harvard admissions counselor misunderstood and thought this was deep stuff and admitted her. Then she spent the next four years doing her best to flunk out. Drugs and boys. Still, she graduated. Another friend did get tossed out of Harvard, but it took some major drug use for that to happen.

Deresiewicz compares the treatment of students at Cleveland State v. Yale. 

In short, the way students are treated in college trains them for the
social position they will occupy once they get out. At schools like
Cleveland State, they’re being trained for positions somewhere in the
middle of the class system, in the depths of one bureaucracy or
another. They’re being conditioned for lives with few second chances,
no extensions, little support, narrow opportunity—lives of
subordination, supervision, and control, lives of deadlines, not
guidelines. At places like Yale, of course, it’s the reverse. The elite
like to think of themselves as belonging to a meritocracy, but that’s
true only up to a point. Getting through the gate is very difficult,
but once you’re in, there’s almost nothing you can do to get kicked
out. Not the most abject academic failure, not the most heinous act of
plagiarism, not even threatening a fellow student with bodily harm—I’ve
heard of all three—will get you expelled. The feeling is that, by gosh,
it just wouldn’t be fair—in other words, the self-protectiveness of the
old-boy network, even if it now includes girls. Elite schools nurture
excellence, but they also nurture what a former Yale graduate student I
know calls “entitled mediocrity.” A is the mark of excellence; A- is
the mark of entitled mediocrity. It’s another one of those metaphors,
not so much a grade as a promise. It means, don’t worry, we’ll take
care of you. You may not be all that good, but you’re good enough.

Steve and I are in frequent talks about whether or not we should move to a town with an Ivy League feeder school. I worry that he’s not getting polished or groomed for excellence. But then a lot of kids I knew burned out early or hit major league depression at not achieving all they were supposed to. (We had a good chat about all this here.) I have to say that I was very assured when I learned that our town’s high school produced Tyler Cowen and David Remnick, but I’m probably the only person in town who knows who they are.

(Thanks to Melissa for the link!)