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Photo's afterlife leaves Romney rueing the day he flashed the cash

But the presidential contender is far from the first to count the cost of an unfortunate image

It is a photo of six corporate raiders, grinning and brandishing dollar bills to underline the success of their company. And none is preppier, more handsome and more delighting in his trade than the man the middle – who just happens, 20 years later, to be front-runner for the Republican presidential nomination.

Political candidacies in the US are defined by many things: words, personality and money. Perhaps above all, however, they are defined by images. This picture of Mitt Romney at the helm of private equity firm Bain Capital could sum up a man making his pitch based on his record as a super-competent executive: the man who rescued the 2002 Salt Lake City Olympics; who was a well-regarded governor of Massachusetts.

Alas, the photo might suggest another Romney, the master of the leveraged buyout and dark financial arts, that made a few people like himself extremely rich, but cost the jobs of thousands of people employed at companies acquired by such techniques. Were this to happen, the moment could scarcely be worse.

On the Tea party right as well as the Democratic left, disgust at high finance and its cosy links with government grows by the day. The protest movement "Occupy Wall Street" is catching the national imagination; just this week a hedge fund king was handed a record jail sentence for insider trading. Could Mitt Romney morph into a latter-day Gordon Gekko, at a time when greed is most definitely not good? The answer is: probably not.

Yes, a photo can have a devastating effect on a presidential campaign. Exhibit A is probably the shot of Michael Dukakis, the Democrats' 1988 candidate, grinning from beneath a helmet, inside a battle tank. It was meant to show support for the military. It managed only to look ridiculous, b oosting Republican claims that a Democrat could not be trusted with national security.

Dukakis atop the tank has entered the chamber of horrors of American political lore. Ronald Reagan's pollster, Richard Wirthlin, later described it as "one of the classic political blunders. You can't stretch the candidate. You've got to portray who he naturally is."

In truth, though, that can also prove dangerous– as evidenced by a strong contender for Exhibit B in the gallery of unfortunate photos. In 2004, John Kerry played the populist in a bid to unseat that child of privilege, George W Bush.

Yet an image of Kerry windsurfing off the exclusive resort of Nantucket reminded people that this champion of the working man was (thanks to his wife Teresa, heiress to the Heinz grocery fortune) the richest man in the Senate.

The Romney picture hardly meets these standards. It is not new. He left Bain in 1999, a dozen years ago, and the picture probably was taken well before then, and first published in 2007. The ones that really wound are contemporary – the Dukakis photo in 1988, the Kerry windsurfing shot from 2004.

This is not to say he is immune. A new photo that nails Mr Romney's vicar of Bray-like ideological slipperiness could become the emblem of his campaign.

But even "flip flopping", one suspects, is not the Republican front-runner's greatest vulnerability. How about a juicy photo of Mitt in Mormon garments, girded up to engage in a"cult" ritual? In God-fearing Republican America, that may turn the primary campaign on its head.

Snapped: Pictures they lived to regret

1. Mitt Romney

When Mitt Romney and his colleagues at Bain Capital had taken the company brochure picture, they decided it might be fun to take another – and posed brandishing $10 and $20 bills. Romney himself, grinning broadly, is pictured with a note poking out of his suit jacket. The picture was dug up by the Boston Globe in 2008, when Romney last ran for the presidency; now it has been revived by Gawker.

2. David Miliband

David Miliband's Labour leadership ambitions hit an early snag when he was widely mocked for an ill-advised photo opportunity with a banana at the 2009 party conference.

3. John McCain

Snapped leaving the stage after the final debate in the 2008 US Presidential elections. "Zombie McCain" became an online sensation.

4. Michael Dukakis

An attempt to prove his bravado backfired when the photo of Democratic hopeful Michael Dukakis in a tank was made into an ad ridiculing him as soft on defence during the '88 presidential campaign

5. William Hague

What started as a publicity stunt to promote a more youthful image of the Conservative Party ended in ridicule: the Daily Mail said the leader "looked like a child-molester on a day-release scheme".

6. David Cameron

The owner of the famous Bullingdon Club photo may have withdrawn publishing rights, but the notorious 1986 image of the Prime Minister and Boris Johnson posturing alongside other Bullingdon members has irrevocably tied the party to the elitist Eton dining club.