Editor's note: This article has been updated to be more up to date with the current presidential administration. Updated on January 20, 2017.

When Donald Trump is sworn in on January 20, 2017, he will officially be the president with the least experience entering office in modern history. It is not rare to see political novices run for high office, but their much broader success in winning support is a more contemporary trend.

Ted Cruz, Rand Paul, and Marco Rubio, all young senators with little experience, ran in the 2016 presidential election along with Trump, as did Ben Carson, a neurosurgeon with no political experience. The anti-establishment tone that was set on both sides of the political aisle resulted in the candidates with the least executive (or political) experience gaining significant grassroots support.

The following list briefly highlights 5 presidents with the least experience prior to taking office. Each man on this list realized varying levels of success and failure and represent many different eras in post-Civil War American history. These facts were taken into account when creating this list.

1. Ulysses S. Grant (1869-1877)

Ulysses S. Grant was elected president less than 4 years after accepting Robert E. Lee's surrender to effectively end the Civil War in April 1865. A West Point graduate and a veteran of the Mexican War, Grant was failing at farming and business when he rejoined the army at the start of the Civil War.

As president, Grant habitually appointed cronies to cabinet positions and "Grantism" became a watchword for "Gilded Age" political corruption. The most notorious scandal was the "Whiskey Ring," where distillers were bribing federal agents not to collect excise taxes. When the ring was broken, Grant's personal secretary was indicted.

2. Grover Cleveland (1885-1889 and 1893-1897)

Typically remembered as the only president elected to two non-consecutive terms, Cleveland emerged rapidly. Prior to becoming president, Cleveland served as mayor of Buffalo, New York for less than one year. His service impressed his party (the Democratic Party) so much that he was nominated to represent Democrats in the 1882 New York governor's race and won.

Although a Democrat, Cleveland enjoyed a renaissance among modern conservative Republicans due to his opposition to tariffs and imperialism and his support for the gold standard. Cleveland lost re-election in 1888 despite narrowly winning the popular vote, but he returned to win in 1892.

However, his second term was hobbled by the Panic of 1893 and the conservative Cleveland was replaced in 1896 as the Democrats' standard-bearer with the firebrand William Jennings Bryan.

3. Woodrow Wilson (1913-1921)

An academic and president of Princeton University, Woodrow Wilson was governor of New Jersey for two years before winning the presidency. The GOP's split between Theodore Roosevelt and William Howard Taft allowed Wilson to become the second Democrat to win the White House since 1856.

A progressive, Wilson oversaw the enactment of the Federal Reserve, the income tax, and the direct election of U.S. senators. Wilson was re-elected on the slogan, "He kept us out of war," but involved the country in World War I one month after his second inauguration.

Wilson, perceived by many to be a stubborn partisan, signed the Espionage Act of 1917 and battled the Senate's Republican majority over ratification of the Treaty of Versailles.

4. Dwight Eisenhower (1953-1961)

The Supreme Commander of Allied Forces in World War II was such an unknown to the political world that he may not have even voted prior to running for president. His party affiliation was so murky that Democrats considered drafting him in 1948 to replace sitting president Harry Truman.

Although lacking political experience, Eisenhower successfully resolved the Suez Canal crisis in 1956 and refused to involve the U.S. in Indochina. Eisenhower won two terms as president, establishing the Interstate Highway System and signed the Civil Rights Act of 1957.

5. George W. Bush (2001-2009)

The son of a president, grandson of a senator, and a graduate of Harvard and Yale, George W. Bush had the pedigree of a president. After losing a congressional race in 1978, achieving sporadic success in the oil industry, and minority-owning the Texas Rangers baseball club, Bush was elected governor of Texas in 1994. Critics at the time and since have noted that the Texas governor does not hold as much power and influence as other governors and therefore was not a relevant formative guide for the presidency.

Bush experienced unusually high approval ratings in response to his leadership after the September 11, 2001 terrorist attacks -- reaching as high as 92 percent. However, the lingering war in Iraq, the sluggish federal response to Hurricane Katrina, and a financial crisis marred Bush's time in office, particularly his second term. By the time he left office in 2009, Bush had the lowest approval ratings since Watergate.

6. Donald J. Trump (2017-)

Donald Trump's campaign focused on the fact that the businessman and real estate mogul was a political outsider. His campaign was mocked by members of the press, and his positions and style were rebuked by leaders of both major political parties. Before taking the Oath of Office on January 20, 2017, Trump never held an elected office of any kind, making him the least experienced president in modern -- perhaps all -- U.S. history.

Trump ran on a populist message that he was going to "Make America Great Again," focusing on trade, jobs, immigration, fixing health care, infrastructure, and other issues that tend to resonate with the average working class American. It worked. Trump's anti-establishment campaign was able to flip districts in key states previously won by President Barack Obama, giving him an electoral victory.