President Donald Trump has a big ego, to say the least. Before taking office, he loved nothing more than flying around in his private jetliner, talking about his billions of dollars in wealth and plating his surroundings with gold.

As unseemly as Trump’s talk of his own wealth may have been, there is one silver lining: The other very wealthy men the United States has elected to the presidency have, by most accounts, done a good job in office. Looking at their accomplishments and their faults may provide some insight as to what Trump will do.

While it’s difficult to convert holdings of the distant past into modern dollars, it appears that three previous presidents almost certainly would have ranked among the 500 or so wealthiest Americans in their times: President George Washington, President Thomas Jefferson and President John F. Kennedy. Kennedy ranks high in polls that ask the general public to name the great presidents and does fairly well among professional historians, as well. Nearly every poll of historians puts Washington among the top three presidents in American history and Jefferson is generally in the top five.

Like Trump, none of the three mega-wealthy presidents were self-made. All had significant inherited wealth and the one who managed it most directly (Jefferson) lived beyond his means and died deeply in debt. While none matched Trump for ostentation, the other very wealthy presidents weren’t modest about wealth. Washington owned one of the largest houses of his day and Kennedy became famous for his upper-class playboy lifestyle. Jefferson and Kennedy, like Trump, were also known for having active sex lives and a number of rumored relationships outside of marriage.

Like Trump, the three super-rich men elected to the presidency all had strong maverick streaks. In office, all three turned against their own presumed bases and stated interests. Washington, a British military officer and member of the New World British establishment, turned his back on the country he had vowed to serve, taking up arms in violent rebellion to create a new nation. Jefferson, ever the believer in limited government, stretched the then-ill-defined powers of his office to more than double the country’s territory with the Louisiana Purchase. Kennedy took on the left of his own party when he took a hard line against communism and for tax relief, while simultaneously angering the same party’s racist right wing by standing in support of civil rights

All three were quite willing to use military force when displeased: Washington led the Continental Army in the Revolution, Jefferson dispatched naval forces to fight the Barbary pirates in the first major overseas engagement by the U.S. military, and Kennedy escalated the war in Vietnam.

Jefferson and Kennedy each also engaged in one truly spectacular blunder. Jefferson, for his part, caused an economic depression by declaring a near-total trade embargo on foreign goods. Kennedy’s high-flying rhetorical support of freedom dragged the country into an expensive, corrupt and futile war in Vietnam.

It’s difficult to know whether any of these similarities are tied, even indirectly, to their wealth, but it’s tempting to think that some might be. While no former president in the modern era will face anything other than a very comfortable life post-presidency, having great wealth allows people to know that they can retain influence and power, even if they alienate their own bases, which may explain the very rich president’s tendency to go against the grain.

Likewise, it seems plausible that men used to having every material need satisfied might be more willing to use force when a foreign power acts against what they perceive as the national interest. The same “consequences don’t matter” attitude may lead to a heightened willingness to pursue sexual relations outside of marriage. Since the very wealthy almost always attract sycophants, it’s possible that major blunders come from failing to seek a wide enough circle of counsel.

It’s impossible to know for sure if any historical patterns will hold when it comes to Trump. To date, the man has defied every historical rule. But history tells us that very wealthy men have made pretty good presidents.

Image by STILLFX


Featured Publications