This research examines three case studies involving four pregnant women facing capital punishment in seventeenth and eighteenth century colonial America. A relevant biography, background, and criminal history are given for each woman as well as a thorough overview of related legal proceedings. This work implements trial transcripts, letters, journals, and newspaper articles to fully portray each woman’s story as precisely as possible, as well as modern sources to help interpret laws and procedures. This work also includes an overview of the legal process a woman must go through if facing capital punishment when pregnant. The purpose of this work is to tell the women’s stories and explain why the courts made the decisions they did in each case. In order to understand the courts’ decisions, the role of women in crime is examined. By allowing the women to “plead their bellies,” the courts acknowledged motherhood as significant enough in women’s societal roles to override a death sentence. Although crime itself was seen as masculine, pregnancy allowed criminals to assume a feminine role once more. The aftermath of a plea when granted or denied is also examined, as each individual case differs.