Grover Cleveland was an American politician and lawyer who was the 22nd and 24th president of the United States, the only president in American history to serve two non-consecutive terms in office (1885-1889 and 1893-1897).

In 1870, he secured the Democratic nomination for Sheriff of Erie County, New York. He won the election by a 303-vote margin and took office on January 1, 1871 at age 33. During his two-year term, he personally carried out the death sentence (by hanging) of three convicted murderers.

With the American Civil War raging, Congress passed the Conscription Act of 1863, requiring able-bodied men to serve in the army if called upon, or else to hire a substitute. Cleveland chose the latter course, paying $150 (equivalent to $3,115 in 2019) to George Benninsky, a thirty-two-year-old Polish immigrant, to serve in his place.

Cleveland grew up in upstate New York. In 1881, he was elected Mayor of Buffalo and later, governor of New York. His defiance of political corruption won him popular acclaim, as well as the enmity of the influential Tammany Hall organization in New York City.

In 1874, Cleveland had courted a widow, Maria Halpin. She later accused him of raping her. In an attempt to discredit her, he had her institutionalized, and their child taken away and raised by his friends. The institution quickly realized that she did not belong there and released her. The illegitimate child became an issue during his first presidential campaign, prompting Cleveland's opponents to adopt the chant, "Ma, ma, where's my pa?" After Cleveland won the election, the chant was answered by, "Gone to the White House, ha, ha, ha!"

Cleveland was one of only two Democrats (with Woodrow Wilson) to be elected president during the era of Republican political domination dating from 1861 to 1933.

The 1884 campaign focused on the candidates' moral standards, as each side cast aspersions on their opponents. Cleveland's supporters rehashed old allegations that Republican James G. Blaine had corruptly influenced legislation in favor of the Little Rock and Fort Smith Railroad and the Union Pacific Railway, later profiting on the sale of bonds he owned in both companies. Although the stories of Blaine's favors to the railroads had made the rounds eight years earlier, this time Blaine's correspondence was discovered, making his earlier denials less plausible. On some of the most damaging correspondence, Blaine had written "Burn this letter."

Thomas A. Hendricks defended the Southern position in the U.S. Senate during the American Civil War and Reconstruction era and voted against the Thirteenth, Fourteenth, and Fifteenth Amendments to the U.S. Constitution. Although he had been in poor health for several years, he was selected as Grover Cleveland's running mate and served as vice president during the last eight months of his life, from his inauguration on March 4 until his death on November 25, 1885. After Hendricks' death, the vice presidency remained vacant for the remainder of Cleveland's first term.

Unlike the previous bachelor president James Buchanan, Cleveland did not remain a bachelor for long. In 1885, the daughter of Cleveland's friend Oscar Folsom visited him in Washington. Frances Folsom was a student at Wells College. When she returned to school, President Cleveland asked her mother's permission to correspond with her, and they were soon engaged to be married. On June 2, 1886, Cleveland (age 49) married Frances Folsom (age 21) in the Blue Room at the White House. He was the second president to wed while in office.

He pushed for the passage of the Dawes Act, which provided for distribution of Indian lands to individual members of tribes, rather than having them continued to be held in trust for the tribes by the federal government. While a conference of Native leaders endorsed the act, in practice the majority of Native Americans disapproved. It ultimately weakened the tribal governments by allowing individual Indians to sell land and keep the money.