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Jessie Wallace Hughan was a trailblazing 20th century woman who was a New York City public school teacher and fervent antiwar activist. Although her role in founding the War Resisters League (WRL), the oldest secular antiwar organization in the United States in 1923, is well documented, there is a gap in the scholarship that focuses on Hughan’s academic background and teaching career during the first Red Scare. Therefore, the purpose of this paper is to explore Hughan’s biography—including but not limited to her childhood, her teaching career, and her political influences— in order to analyze how current matters of academic freedom continues to impact 21st-century education.