Winter caught his biggest break in December 1968, when Mike Bloomfield, whom he met and jammed with in Chicago, invited him to sing and play a song during a Bloomfield and Al Kooper concert at the Fillmore East in New York City. As it happened, representatives of Columbia Records (which had released the Top Ten Bloomfield/Kooper/Stills "Super Session" album) were at the concert. Winter played and sang B.B. King's "It's My Own Fault" to loud applause, and within a few days, was signed to what was reportedly the largest advance in the history of the recording industry at that time—$600,000.