Trevor Smith was born in East Flatbush, Brooklyn to Jamaican parents Geraldine Green and Trevor Smith, Sr. When he was 12 his family moved to Uniondale, New York, a suburb of Nassau County, where he was raised and eventually met up with other artists from the growing area hip hop community. He graduated from Uniondale High School in 1991.

Smith's musical career began at the age of 17 as a member of the hip hop crew Leaders of the New School along with fellow Long Island natives Charlie Brown, Dinco D, and Cut Monitor Milo. They began recording in 1989 and released their debut album A Future Without a Past in 1991 on Elektra Records. In 1993, they released T.I.M.E. (The Inner Mind's Eye). Soon after, however, internal problems arose within the group, and the group broke up on the set of Yo! MTV Raps. Rumors persisted that Smith clashed with Charlie Brown over creative control of the group's direction.

Soon after their debut, The Leaders of The New School became associated