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Gregory used his newfound fame to become a civil rights activist and opponent of the Vietnam War. He made friends with Martin Luther King Jr. and Malcolm X; honored a request from Medgar Evers to speak at a voter registration rally in Jackson, Miss.; delivered food to NAACP offices in the South; marched in Selma, Ala.; got shot while trying to keep the peace during the 1965 Watts riots; was arrested in Washington for protesting Vietnam; performed benefit shows for the Congress of Racial Equality; and traveled to Tehran in 1980 to attempt to negotiate the hostages’ release.
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Gregory ran for mayor of Chicago in 1967 but lost to Richard Daley, then entered the race for U.S. president a year later. A write-in candidate on the Peace and Freedom Party ticket, he received some 47,000 votes.
“Had I won, the first thing I would do is dig up that Rose Garden and plant me a watermelon patch,” Gregory said in 2016. “And it would be no more state dinners, but watermelon lunches. We’d eat watermelon and spit the seeds on Pennsylvania Avenue.”