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Illustration by 731, Photograph by Getty Images Illustration by 731, Photograph by Getty Images

Mitt Romney’s fundraising events in the Hamptons yesterday wouldn’t have looked much different if the Obama campaign had organized them on his behalf. From the ostentatious mega-mansions, to the Bentleys and Ferraris, to the guests’ crass boasting about their yachts and condescending put-downs of the poor and middle class, the whole scene seemed designed to reinforce Team Obama’s preferred image of Romney as an out-of-touch plutocrat concerned only for those with a comparable net worth.

For Romney, just back from a jet-skiing vacation at his lakeside manse in New Hampshire, the events will raise lots of money and put further distance between himself and the president. In June, he and the Republican National Committee outraised President Obama and the Democratic National Committee $106 million to $71 million. But every time Romney draws attention to the unseemly aspects of his wealth (or when his supporters do, like the Hamptons crowd), he undercuts that fundraising advantage and hurts his candidacy. He does this a lot: bragging about his multiple Cadillacs, proposing a $10,000 bet during a GOP debate, boasting of his friendship with NFL owners. Romney’s problem is that while he was very good at getting rich, he isn’t any good at being rich. In fact, he’s downright terrible at it.

This is partly Romney’s fault and partly the fault of his party.

As the GOP primaries revealed, Romney has a strange compulsion to talk about his wealth in unbecoming ways: joking to a group of unemployed people, for instance, that he, too, is unemployed. James Fallows dubbed this Romney’s “gaffe Tourettes.”

More often, though, Romney invokes his wealth as a political defense in a way that’s clearly intentional and no less unattractive. Questions about everything from his business practices at Bain Capital to the problem of growing income inequality are routinely met with the claim that people are just jealous of all his money. A good example is this Today Show interview with Matt Lauer wherein Romney dismisses Lauer’s questions about income inequality as “very envy-oriented” and a matter best discussed in “private rooms.”

Wealthy presidents from John F. Kennedy to George W. Bush were far more gracious and thoughtful about the subject of their wealth, and, not coincidentally, more successful politically than Romney has been when speaking about his own. Democrats have it easier, since their policies skew more toward helping the poor. But Republicans have managed. Bush’s approachable, rough-hewn friendliness and “compassionate conservatism” blunted the problem of his wealth; the spirit of noblesse oblige instilled in George H.W. Bush’s generation of Republicans helped him.

But that spirit is all but gone from today’s Republican Party, replaced by an intense devotion to laissez-faire capitalism that’s often accompanied by a sense of entitlement and persecution, which was vividly on display in the Hamptons. This scene from the Los Angeles Times story on the fundraisers captures it well:

“I don’t think the common person is getting it,” [a Romney donor] said from the passenger seat of a Range Rover stamped with East Hampton beach permits. “Nobody understands why Obama is hurting them.

“We’ve got the message,” she added. “But my college kid, the baby sitters, the nails ladies — everybody who’s got the right to vote — they don’t understand what’s going on. I just think if you’re lower income — one, you’re not as educated, two, they don’t understand how it works, they don’t understand how the systems work, they don’t understand the impact.”

Everything Obama and his allies have done to date—from the Bain attack ads to the questions about Swiss bank accounts to today’s proposal to extend the Bush tax cuts only for those making less than $250,000—is designed to convince voters that Romney holds this view of them and would govern in a style commensurate to these values. And Romney has shown little aptitude for convincing them otherwise.