Mitt Romney is one of the richest men to run for President of the United States.
Wealth is a challenge for a Presidential candidate, because it can set up a essential "otherness" to the politician that creates a barrier between them and the voter.
George H.W. Bush was (inaccurately) believed to have been caught unawares by a grocery check-out scanner in 1992, reinforcing an image of an out-of-touch elitist who sent his chauffer to pick up his milk.
John Kerry was merciless ribbed for his wealth, in part because it was his wife's in most part.
Steve Forbes never gelled with the public, in part due to his other-worldliness as a man worth half a billion dollars.
But some of American's greatest presidents were also clearly wealthy.
George Washington, James Madison and Thomas Jefferson were among the largest landholders in Virginia.
Theodore and Franklin Roosevelt and John Kennedy were all born into privilege.
How did these earlier Presidents "overcome their handicap" and win?
The Extension of the Franchise
For Washington, Madison and Jefferson, wealth wasn't an issue because the electorate was wealthy.
The franchise was limited in a variety of ways in the early days of the Republic.
Beyond the limitations on voting rights for women, blacks and Natives, property was a requirement for voting among white men until 1820. Voting restrictions on the poor – in the form of "poll taxes" – were used in disenfranchise blacks until the 1960s.
Championing the People
Teddy Roosevelt's road to the White House is rather extraordinary.
Author. State Assemblyman. Rancher. Civil Service Commissioner. New York Police Commissioner. Assistant Secretary of the Navy. War Hero. Governor.
Roosevelt spent his life fighting for the average American, be it against corruption, patronage, crime, or imperialism.
He was a national figure and exceptional personality, with a combination of intellect, physical courage and masculinity that is without equivalent in our day. He's as if Norman Mailer wrote books about naval warfare and played tight end for the 49ers.
What is clear about Roosevelt is that he was fearless in taking on powerful interests to better the lot of the common man.
A Famous Name
Both Franklin Roosevelt and John Kennedy inherited famous names that helped their careers.
FDR was a distant cousin of Roosevelt, but his famous surname got him the vice presidential nomination in 1920 on a thin resume and 38 years of age.
Jack Kennedy was the son of a famous banker, investor, SEC chairman and Ambassador to Britain. That legacy cut both ways, but his father's ambitions for his sons gave Jack Kennedy the push into political success few other enjoy.
Many men have had wealthy dads who wanted them to be President. What made FDR and JFK successful was not just the early boost their wealth provided.
Both enjoyed the political skill and charm that this wealth was seen as making them independent of powerful forces, not their servant.
For FDR especially, he was consistent in taking on Wall Street and the wealthy. In fact, one of the best biographies of Roosevelt is called " Traitor to His Class."
Conrad Black's also excellent biography describes Roosevelt as saving the capitalists from socialism in spite of their own pigheadedness through policies that preserved the free market with reform rather than revolution.
Many of Jack Kennedy's bitterest enemies were the wealthy and their organs like the Wall Street Journal and Fortune.
Sadly for Mitt Romney, there isn't a lot of opportunity to mimic history.
The franchise won't be tightened (at least not by November). Few would accuse Mr. Romney of championing the people.
There is some hope in his name, but his father is famous outside of Michigan for saying he was brainwashed into supporting the Vietnam War.
Perhaps Mr. Romney's only hope is to be a traitor to his class.
The best way for him to make a virtue of his money is to run openly and consistently against Wall Street.
Right now, people are suspicious of his motives. The best way to address concerns that you are the ally of powerful and unpopular interests is to give the powerful and unpopular interests a good kick.