The man on the horse is Andrew Jackson. The cigar is a Rocky Patel Edge.
Wiki: During the Revolutionary War, Jackson, at age thirteen, informally helped the local militia as a courier. His eldest brother, Hugh, died from heat exhaustion during the Battle of Stono Ferry, on June 20, 1779. Jackson and his brother Robert were captured by the British and held as prisoners; they nearly starved to death in captivity. When Jackson refused to clean the boots of a British officer, the officer slashed at the youth with a sword, leaving Jackson with scars on his left hand and head, as well as an intense hatred for the British. While imprisoned, the brothers contracted smallpox.
Robert Jackson died on April 27, 1781, a few days after their mother Elizabeth secured the brothers' release. After being assured Andrew would recover, Elizabeth Jackson volunteered to nurse prisoners of war on board two ships in Charleston harbor, where there had been an outbreak of cholera. She died from the disease in November 1781, and was buried in an unmarked grave. Jackson became an orphan at age 14. Following the deaths of his brothers and mother during the war, Jackson blamed the British for his losses.