Born male, Shupe grew up in southern Maryland as one of eight children. He and his wife, Sandy, were married in 1987; and has one daughter. He served in the U.S. Army for 18 years, receiving a number of military decorations, and retired in 2000 as a sergeant first class. Shupe has written that he was physically and sexually abused by relatives during childhood. He recalls his mother punishing him for behaving like a "sissy", and says that he was denied the right to explore his gender expression or gender identity. That suppression continued through his military career, which included periods before and during Don't ask, don't tell. After he retired, Shupe began living as a transgender woman in 2013. He chose the gender-neutral first name "Jamie" and convinced the Army to change his sex marker to female on military records. In June 2016, Shupe successfully petitioned a Multnomah County, Oregon, court to change his sex designation to non-binary, in the first legal recognition of a non-binary gender in the United States. That November, he was issued a birth certificate in Washington, D.C., with a sex marker of "unknown". Lambda Legal later cited Shupe's petition as a legal precedent for non-binary gender markers in the passport lawsuit Zzyym v. Pompeo. Shupe is a critic of transgender surgeries, cautioning against what he says are high complication rates. He has also expressed opposition to transgender people serving in the military. In 2018 Shupe and his wife moved to Ocala, Florida where Shupe says he feels safe and in a community that aligns well with his values. In January 2019, Shupe announced that he no longer identified as non-binary and was returning to identifying as male. He said that his original motivation for transition was autogynephilia and that he was experiencing symptoms of psychosis when he sought a non-binary sex marker. In March, Shupe changed his first name back to James. In December of 2019, Shupe successfully petitioned the court which granted the "non-binary" gender designation to revert the sex listed on his birth certificate to "male." The petition filed by Shupe described the sex designation of non-binary as "psychologically harmful legal fiction."
