A five-time Olympic track and field medallist (four golds), Meyer Prinstein won his first gold medal in the 1900 Paris Olympics Triple Jump with a leap of 47' 53/4" (14.47 meters). That year, he also took a silver medal in the Long Jump event with a mark of 23' 61/2" (7.175 meters).

At the 1904 St. Louis Olympiad, Prinstein captured gold medals in the Long Jump, setting an Olympic record of 24' 1" (7.34 meters) and the Triple Jump with a mark of 47' 1" (14.35 meters).

At the unofficial Athens Olympics in 1906, Prinstein again took gold medal honors in the Long Jump with a leap of 23' 71/2" (7.20 meters). Prinstein's lone silver medal was a subject of controversy at the 1900 Games. At the completion of the Long Jump trials on Saturday, he was leading the competition. The finals were scheduled for the following day. As a Methodist Syracuse University student, Prinstein was instructed, along with many other American student athletes, not to compete on Sunday, the Christian sabbath. While he followed instructions, a few other American athletes did compete on that Sunday, including his Long Jump arch rival, University of Pennsylvania's Alvin Kraenzlein.

In Prinstein's absence and with six unchallenged leaps, Kraenzlein managed to top the Syracuse undergraduate's event-leading mark to win the gold medal. Prinstein also won many National U.S. track titles, his first in 1898. In 1900, he set the World Long Jump record at 7.50 meters.