There's something a little silly about Hillary Clinton's efforts to label Barack Obama "the establishment candidate" considering that she's also bragging about her lead in superdelegates, is running on experience, and is backed by the bulk of the senior leadership cadres from her husband's administration. And of course, her husband used to be president.
At the same time, it's clearly true that many well-established figures have flocked to the Obama banner at this point. It's not like he's running a small gritty insurgent campaign based on a handful of longtime loyalists from his home state plus a rogue political strategist. From Day One in the Senate, Obama's attracted very experienced, very high-profile people to his cause and the further he goes the more that happens.
The main difference is that the establishment that's behind Clinton comes much closer to being worthy of talked about as a unitary entity. Team Clinton is composed of people from all dimensions of politics -- from interest groups like AFSCME to national security hands like Holbrooke and Albright to pure politics people like Wolfson and Penn -- who've all been working together and working for the Clintons for a long time. Obama has behind him a much more disparate group of people. They're not "outsiders" -- Peter Rouse worked for the Senate Minority Leader, Ted Kennedy's been important forever, Samantha Power won a Pulitzer Prize, all kinds of random prominent pundits like him, Zbig Brzerzinski was National Security Advisor -- but they weren't on the inside of the Clinton administration.
In that sense, an Obama win would represent an alternation of elites. Important left-of-center people who haven't happened to be the most important left of center people over the past 15 years or so would rise to leadership. A Clinton win would be the return of the people who ran the show in the late 1990s and who continued to be the predominant influence in the 21st century. But in neither case are you getting a real toppling of hierarchies and massive infusion of outsiders.