For personal or political reasons undocumented and controversial to this day, Greenwich Village lesbian photographer Angela Calomiris joined forces with the Federal Bureau of Investigation (FBI) during the Second World War to infiltrate the Communist Party of the United States (CPUSA). As Calomiris rose through CPUSA ranks in New York City, espionage efforts resulted in the Attorney General's office declaring the avant-garde Film and Photo League to be a subversive communist organisation in 1947, and the conviction of communist leaders during the Smith Act trial two years later. Interestingly, despite J. Edgar Hoover's indeterminate sexuality and well-documented harassment of gays and lesbians in public life, what mattered to him was not whether Calomiris adhered to heteronormativity, but that her ultimate sense of duty lay with the US government. This article demonstrates how this distinction helped Calomiris find personal satisfaction in defiance of patriarchal conservative expectations and heteronormative cold war gender roles. This article, which utilises FBI files, press coverage, some of Calomiris's papers and her memoir, concludes with a brief discussion of Calomiris's later life in Provincetown, Massachusetts, where she continued to craft her identity as a left-liberal feminist, with no mention of the service to the FBI or her role in fomenting the second Red Scare.