Was he a bad teacher? He worked as a writer and held several odd jobs before borrowing his roommate's license to investigate teaching. Gatto also ran for the New York State Senate, 29th District in 1985 and 1988 as a member of the Conservative Party of New York against incumbent David Paterson. He was named New York City Teacher of the Year in 1989, 1990, and 1991, and New York State Teacher of the Year in 1991. In 1991, he wrote a letter announcing his retirement, titled I Quit, I Think, to the op-ed pages of the Wall Street Journal, saying that he no longer wished to "hurt kids to make a living." He then began a public speaking and writing career, and has received several awards from libertarian organizations, including the Alexis de Tocqueville Award for Excellence in Advancement of Educational Freedom in 1997.