Prinstein won the silver medal in the long jump at the 1900 Summer Olympics in Paris, France, losing to Alvin Kraenzlein after being denied permission by Syracuse officials to compete in the final because it was contested on a Sunday – despite the fact that Prinstein was a Jew, and Kraenzlein, who was a Christian, did compete. The two had had an informal agreement not to compete on Sunday, and when Prinstein learned that Kraenzlein had competed he became angry and, depending on the account, punched Kraenzlein in the face or was restrained from doing so. The following day, he won the gold medal in the hop, step and jump (triple jump), beating 1896 champion James Connolly with a leap of 14.47 meters which simultaneously set the Olympic Record.