The size and placement of the bronze equestrian statue portraying Ulysses S. Grant is a testament to Grant's relationship to Chicago and the state of Illinois. Though born in Ohio, Grant was a central figure in Illinois' Civil War experience. The majority of Illinois men fighting for the Union were assigned to the Army of the Tennessee and the Army of the Cumberland, both of which at various times were under Grant's command. Additionally, Grant's capture of Confederate prisoners at the Battle of Fort Donelson led to the conversion of Chicago's Camp Douglas from a training camp for Union soldiers into a prison for Confederate captives.

Grant was in the minds of Chicagoans again in 1868 when the Republican National Convention nominated him for president from Chicago's Crosby Opera House. Grant went on to win the election and served two terms as president.

The city of Chicago dedicated Grant’s equestrian monument in Lincoln Park in 1891, six years after his death. 250,000 Chicagoans attended the ceremony. Louis Rebisso, an Italian immigrant, designed the statue, which was placed on top of a granite base constructed by William LeBaron Jenny. Jenny had served as a military engineer under Grant during the Civil War.

Statuary was a popular choice for memorializing Civil War figures in the late nineteenth and early twentieth centuries. Not far from here stands the famed “The Man" (also known as "The Standing Lincoln") memorial of President Lincoln, dedicated in 1887, and a statue of Civil War General Philip Sheridan, dedicated in 1924. A statue of Lincoln (known as "The Sitting Lincoln") done by Augustus Saint-Gaudens stands in Grant Park (which was named after Grant in 1901). Also in Grant Park is Saint-Gaudens’ memorial to Civil War General John A. Logan, dedicated in 1897.

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