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Two notable examples of people who have won elections while in jail or prison are:
Eugene V. Debs: In 1920, Debs received one million votes in the U.S. presidential election on the Socialist Party ticket while serving a 10-year sentence for his speech protesting World War I. He was imprisoned in the Atlanta penitentiary during the election.
Joel Caston: In 2021, Caston became the first incarcerated person in Washington, D.C., to win elected office. He won the race for advisory neighborhood commissioner of a district where he would oversee the Harriet Tubman Women’s Shelter and D.C. Jail, where he was an inmate.
These examples highlight that while it is uncommon, it is possible for individuals to win elections while in jail or prison. However, the process of voting and running for office while incarcerated can be challenging, as access to crucial information and election forms is often limited.
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Nov. 2, 1920: Imprisoned Eugene V. Debs Received One Million Votes for U.S. President
https://www.zinnedproject.org/news/tdih/debs-received-million-votes/