Freeman graduated from high school at the age of 12 and enrolled at the University of Chicago, earning a bachelor’s degree in liberal arts by the age of 15. At the age of 21, he had earned another bachelor’s degree (in business administration) and a law degree from George Washington University in DC.

Freeman became the ACBL’s youngest Life Master in 1952 at the age of 18. In the mid-Fifties, he began directing and became legendary for his speed with a pencil in the days when games were posted and scored by hand.

He won his first North American championship in 1955 — the Men’s (now Open) B-A-M Teams — playing with Edgar Kaplan, Norman Kay, Ralph Hirschberg and Al Roth.

Freeman is best known, however, for his partnership with Nick Nickell and for the success their team — Bob Hamman–Bobby Wolff, Paul Soloway, Jeff Meckstroth–Eric Rodwell — enjoyed for many years: the Spingold in 1993, 1994, 1995, 1996, 1998 and 1999; the Reisinger in 1993, 1994 and 1995; the Vanderbilt in 2000 and the Bermuda Bowl in 1995 and 2000.

Freeman says he considers bridge to be more than a game, more than a sport — "it broadens your perspective." He credits his wife, Louise, with teaching him how to win.