Richardson associates Hillary with Bush as part of the status quo when he says we've had the same families running the show since Bush Sr., and also says that she feels entitled to the presidency. He doesn't say why she feels entitled, but the only logical conclusions are that she was the First Lady, let her political career take a backseat to Bill's, or that she "has 35 years of experience" and has made connections within the party and is extremely loyal to the party, and thus deserves the nomination over a newcomer.
Every single time Hillary utters the word "experience," she plays into the role Obama has written for her as the establishment candidate. This is the same thing Reagan did to Democrats. As Obama puts it in The Audacity of Hope, "Reagan offered America a common sense of purpose that liberals seemed no longer able to muster. And the more and more his critics carped, the more those critics played into the role he'd written for them -- a band of out-of-touch, tax-and-spend, blame-America-first, politically correct elites."
In a speech the same day as Richardson's endorsement, Obama mentioned "[Hillary Clinton, George Bush, and John McCain]" eight times, in reference to the war in Iraq. Now, not only did Hillary support Bush in Iraq, but she also will continue the dual bloodline that's held the last three Presidencies. He paints his opposition into roles very well, and both Hillary and McCain have fallen into playing them or, in McCain's case, has been forced to be more conservative to energize the GOP base; McCain's role will be running for a third Bush term, and no amount of back-peddling will erase his flip-flopping on tax cuts nor his support for the "Bush-McCain War."