Republicans in Washington are feeling pretty confident. This is always a bad sign. Right now, things do seem to be going the GOP’s way. President Obama continues to suffer dismal re-election numbers, and the economy remains as sluggish as Facebook stock.

The latest news ought to give even the White House pause: Mitt Romney and Republicans outraised the president and the Democrats by $16 million in May. Of special note, Romney beat Obama in contributions from Wall Street.

Therein lies a potential problem for the GOP. In the race to define Romney to the American electorate, his friends on Wall Street are not going to be of much help. 

Past and present advisors to Governor Romney are aware that, despite the candidate’s earnest efforts, he is never going to come across as a regular Joe. Often when he attempts this, something delightfully terrible happens: from “I like to fire people” to “I’m also unemployed” to my personal favorite, “Who lets the dogs out?”

Mitt Romney is not the guy who hangs around our local bowling alley gorging on pizza. Romney is the guy who gives nice tips to his caddies every Christmas, wears crisp and colorful shirts with ponies on them, and always remembers to say please when asking Jeeves to bring one of the cars around.  Miraculously, Romney might even make Barack Obama, the Harvard-trained multimillionaire who sniffs at Middle American gun-and-God-clingers, look like Fred Flintstone.

Romney isn’t going to win the election by being the guy with whom America wants to share a beverage.  Romney wins the election if he can convince the country that, though he may be an awkward milquetoast guy, he knows how to save the economy. Voters tends to like the idea of a president with business experience—see Lee Iacocca, Ross Perot, Donald Trump—until, that is, those business leaders turn out to be inexperienced, nutty, or oily (see Iacocca, Perot, and Trump). To that end, Romney’s association with venture capitalists on Wall Street is going to be a problem.

During the Republican primary, questions about Romney’s tenure at Bain Capital tended to backfire, as Republicans took to talk radio and Fox to express umbrage at people daring to offer the slightest criticism of America’s capitalist system. You know, people like left-wing radical Sarah Palin, who complains about “crony capitalism,” and noted Marxist George W. Bush, who said “Wall Street got drunk” during the financial crisis. This week members of Congress from both parties went after Jamie Dimon, the CEO of JP Morgan Chase, who admitted to blowing $2 billion during the financial crisis. The general reaction to that hearing was not that members of Congress were too tough on the guy, but that Congress wasn’t tough enough.

The Romney campaign may believe it can wrap the American flag around his Wall Street associations in the general election. If so, they are probably in for a surprise. Most Americans, struggling to pay their bills and find jobs, aren’t likely to equate anyone with a Harvard MBA with our Founding Fathers.  In fact, most believe the folks at the big investment banks played a major role in screwing up the economy. With good reason, by the way, since they did. Not too long ago, in fact, conservatives also railed against billion-dollar bailouts of Merrill Lynch and Goldman Sachs. And to this day, astonishingly, more Americans blame Bush (and free market Republicans) than President Obama for our current economic mess. The question Americans are in the process of asking about Mitt Romney is not whether capitalism is a good thing, but whether he is a Mr. Fix-It or a Mr. Screwed-It-Up. A Warren Buffet or an Ivan Boesky. How the majority of Americans answer those questions will decide the election.

Romney’s team, then, is going to have to do more than label any attack on Wall Street an attack on America.  Instead he needs to differentiate himself (and Bain Capital) quickly from the Hank Paulsons and Jamie Dimons of the world.  He needs to demonstrate, in a systematic way, how his efforts created new companies and new jobs. Oh, and it might help to get his facts straight too. The last thing anyone wants to be in this election, in this economy, is the candidate of Wall Street.