Dr. Jessie Wallace Hughan was a trailblazing New York City public school educator and pacifist. Hughan was a socialist, and she was among numerous teachers who faced investigations for anti-patriotic activities at the turn of the 20th-century, when teachers across the country faced intense scrutiny and legal challenges if they were suspected of being socialist. Examining the causes and impact of these investigations may bring deeper understanding about Hughan's teaching career, as well as how the ramifications of these investigations from 100 years ago may shed light on current matters of academic freedom in the education profession. The purpose of this paper is to analyze the basis for, and consequences of, the investigations of Hughan in order to provide educational historians, teachers, and other stakeholders insights into why teachers become targets of politically motivated investigations, how educators can be supported and informed about how to navigate teaching controversial issues, and the potential effects such investigations can have on the education profession.