Randy is a 1973 graduate of Oceanside High School in Nassau County on Long Island where he played varsity football.

He left Major League Baseball to become New York City's Deputy Mayor for Economic Development, Planning and Administration from 1997 to 2000.

In January 2000, he announced his resignation from Rudy Giuliani's administration, citing a return to private practice; he was named president of the Yankees the next day.

[7] In December 2018, Levine's name was leaked as a potential replacement for departing White House Chief of Staff John F. Kelly.

Levine is very active in animal rescue efforts and is a proponent of equine-assisted therapy for military veterans.