He is the author of multiple books and a play, and is an outspoken critic of American drug laws.

Gray also introduced Orange County to the Peer Court system, where juvenile defendants travel to a school outside their district to have their actual cases tried by other teenagers.

[1] In 2012, Gray was nominated by Libertarian Party convention delegates as the running mate of former New Mexico Governor Gary Johnson.

[7] In November 2003, he declared his candidacy for the U.S. Senate seat occupied by Barbara Boxer in California.

[14][15][16] He was a proponent of the Regulate, Control and Tax Cannabis Act of 2010,[17] a statewide referendum measure that was defeated in the 2010 California state elections.

While the measure failed to collect the minimum number of signatures needed for qualification to be placed on the ballot in the 2012 statewide election, Gray's active role in the effort prompted media speculation regarding his future in the Libertarian Party and in national politics.

[21] Gray then confirmed his candidacy for the Libertarian vice-presidential nomination in an open letter to the party's Convention delegates.

[24] On April 13, 2020, Gray announced his intention to seek the Libertarian Party's nomination for president with Larry Sharpe as his running mate.