He graduated from the Collegiate School, a co-ed private school in Richmond, in 1981. He enrolled at George Washington University (GW) in 1981; as a freshman he worked as an intern for House Republican Tom Bliley of Virginia, and was Bliley's driver in the 1982 campaign. Cantor was a member of Phi Sigma Kappa fraternity while at GW and received his Bachelor of Arts in 1985. He earned a Juris Doctor degree from William & Mary Law School in 1988, and received a Master of Science in Real Estate Development from Columbia University in 1989.