Last year, Jacobson’s dreams came true when California taxpayers footed the bill for his gender transition surgery, a move made possible thanks to policies and precedents set during Kamala Harris’s time as the state’s attorney general.

"I did receive gender affirming surgery and breast augmentation on April 5th 2023," Jacobson, who now goes by Skylar Deleon, wrote in a letter to the Washington Free Beacon. That letter was sent in response to a Free Beacon inquiry into the status of his transition. Jacobson said he is now awaiting transfer to a women's prison from San Quentin.

Harris's support for inmates like Jacobson emerged as a campaign issue when a CNN report revealed that she pledged in a 2019 ACLU questionnaire to support taxpayer-funded sex-change surgeries for illegal immigrants and prisoners in federal custody. But her history on the issue dates back to at least 2015, during her stint as the Golden State's top cop—a period that Harris has cited on the campaign trail as proof of her tough-on-crime approach.