Benedict Freedman, the son and grandson of writers, was born in New York City in 1919. While in high school he studied accelerated courses for gifted boys and graduated with a medal for mathematics. At fourteen he entered Columbia University as a premed student, but had to drop out at sixteen because of his father's sudden death. For a time Benedict continued private study of higher mathematics. Freedman’s chief interest was in games and recreational mathematics, but he also assisted in writing a textbook and worked on actuarial problems as clerk to a consulting actuary.