Plenty of presidential candidates have pointed to their business acumen in making a case for the White House, most recently Republican Mitt Romney in 2012.
But Trump is a rarity for a major party nominee, since he's never held elected office, a top government post or a high military rank.
In recent election cycles, candidates from the private sector have surged, suggesting voters are more open to politicians with business resumes, though no others have made it as far as Trump.
Many historians, however, see the feat as less a modern development than a throwback to the early days of the republic.
A brief history of the 'businessman president'
"The idea of presidents as businessmen has a long history," Dan Mahaffee, director of policy at the Center for the Study of the Presidency & Congress, told CNN.
Mahaffee noted that many of the earliest Founding Fathers, including George Washington and Thomas Jefferson, had various business interests as plantation owners.
Indeed, America's first president was quite the entrepreneur.
In addition to running the large Mt. Vernon plantation in northern Virginia, Washington also served as head of the Potomac Company, which made canal infrastructure improvements along the Potomac River. And the whiskey distillery he operated on his property was the largest whiskey distillery in America at the time of his death in 1799, producing 11,000 gallons a year, according to the Fred W. Smith National Library for the Study of George Washington.
However, Washington's business success was not without controversy. Like many plantations at the time -- including other plantations owned by presidents -- Mt. Vernon used slave labor. The slaves were only freed after the death of Martha Washington.
But Mahaffee said that in subsequent years, "stronger political institutions and a political class developed," leading to "a shift towards lawyers, career politicians and candidates with military experience -- usually a general who had distinguished himself in a recent war."
The notion of a businessman-president enjoyed a bit of a resurgence during the so-called "Roaring Twenties," a time of economic prosperity for the nation.
Republican Calvin Coolidge, who was president from 1923-1929, famously said, "The chief business of the American people is business." Although Coolidge had been a career politician, he had also been the vice president of the Nonotuck Savings Bank in Northampton, Massachusetts. His administration was defined in part by its hands-off approach to the economy.
His successor, Herbert Hoover, was perhaps the most prominent American businessman to rise to the presidency. His career as a mining engineer made him a multimillionaire, amassing a fortune that The Atlantic Magazine estimated at about $75 million in today's dollars.
But the start of the Great Depression in 1929 marked a shift away from presidents with substantial business experience.
The GOP's 1940 nominee, Wendell Willkie, was the last person before Trump to have never held government office prior to winning the nomination. He had been president of Commonwealth & Southern, a major electric utilities holding company based in New York.
Willkie campaigned against Franklin Roosevelt's New Deal -- he called it an "attack on business" upon accepting the nomination -- but was easily defeated.
But in the 1970s, presidents with entrepreneurial expertise once again emerged.
Jimmy Carter had been a successful farmer prior to being elected, making him a bit of a return to the tradition of the Founders.
And George H.W. and George W. Bush both worked in the Texas oil industry, with the elder Bush having founded his own company and the younger working for various oil firms. Bush also helped lead the purchase of the Texas Rangers professional baseball team, making a profit upon the team's sale in 1998.
Independent candidate and billionaire Ross Perot mounted third-party bids in 1992 and 1996 largely on the strength of his business credentials, getting almost 20% of the vote in the first contest.
And former Massachusetts Governor Mitt Romney, a successful founder of Bain Capital, a private equity firm, and former CEO of Bain and Company, a consulting company, won the Republican nomination in 2012 touting his record in business.
Benefits of private sector experience
It may be no surprise that Republicans have put forward more candidates with business backgrounds. An October Associated Press-GfK poll found that Republican voters preferred private sector leadership experience over experience holding elected office 76% to 22%
. Only 33% of Democrats, meanwhile, saw private sector experience as more important.
Republicans have argued that the qualities of businessmen make them especially fit to be good political leaders, emphasizing their ability to motivate and manage others and make prudent decisions with both short-term and long-term consequences in mind.
Business experience can also provide candidates with a broader understanding of economic issues, which tend to be the top concern of modern voters.
And the Republican Party itself has been increasingly identified with corporate America, advocating business-friendly policies like lower taxes and few regulations. The 2016 platform reads: "Republicans will pursue free market policies that are the surest way to boost employment and create job growth and economic prosperity for all."
While running for president in 2012, Romney even pitched the idea that private sector experience should be a constitutional pre-requisite for the presidency.
And while Romney lost the election to incumbent Barack Obama -- whose background is in constitutional law -- there are indications voters are more receptive to candidates from the private sector than in previous eras.
Given all the news of American debt, said William Seale of the White House Historical Association, "people think that a businessman could come in and fix the situation, manage the books."
And also drawbacks
Yet Trump's business ties also pose a liability. His many international business holdings could create conflicts of interest for him if elected.
In a recent CNN poll, 70% of voters said Trump should cut his business ties
while running for president, demonstrating the sensitivity of the issue.
And if the past is a guide, experience in business hasn't always led to celebrated White House success.
Hoover was blamed for a lackluster response to the Great Depression, and he along with Carter and H.W. Bush were voted out of office after a single term.
George W. Bush, the only president with an MBA, from Harvard Business School, left office as the 2008 recession was underway.
The business record of candidates also hasn't always been a selling point.
Amity Shlaes of the Coolidge Foundation noted that many, including President Harry Truman, a former owner of a haberdashery, were "hard-up financially."
The experience, according to Shlaes, actually caused Truman to lose his faith in commerce, making him less inclined to support big business as president.
"In fact," Seale of the White House Historical Association said, "an awful lot of them were bad businessmen."