John Paine and his brother, Sumner, came from a notable sporting family. Their father, Gen. Charles Jackson Paine had thrice defended the America’s Cup for the United States – in 1885, 1886, and 1887. In 1896 Lt. John Paine was a member of the Boston Athletic Association, which was sending several track & field athletes to the Olympic Games. Paine decided to go over to Athens and on the way, stopped in Paris to meet his brother, who was working at the Gastin-Renette Galleries. John convinced Sumner to join him in Athens and, once there, John easily won the first competition, the military pistol event, over his brother. So easily did he win, in fact, that John thought it unsporting to enter any further events and withdrew from the remaining pistol event. John Paine, an 1891 graduate of Harvard, returned to Boston after the Olympics, but left again in 1898 to fight in the Spanish-American War He later settled in a suburb of Boston, where he became a wealthy investment banker.