In 1997, he enrolled at the University of Rochester and later dropped out to move to New York City and pursue a career in journalism.

[2] He worked there until moving to the Village Voice, where he investigated poverty pimps, and cases against the wrongfully accused.

[3] In 2003, Gray began covering boxing for the New York Times, writing about underdogs in their industries, laborers and legends like Mike Tyson.

In 2008, he produced and narrated a segment of the Showtime series This American Life, which featured a pair of troubled boxers in Tennessee.

"[15] In 2013, Gray produced a feature film, Patrolman P, a documentary about a legendary and corrupt police detective in the 1970s.