Dolly Parton’s Chauffeur and Assistant of 30+ Years Was a Trans Man She Supported and Loved

As the world is still reeling from the news of the death of legendary Queen of Country Music Dolly Parton on Tuesday, many of her LGBTQ+ fans have resurfaced evidence of her long and enduring support of the LGBTQ+ community.That support included a job and a lasting friendship with a transgender chauffeur, Jason Pirro, who previously spoke with the press about Parton, saying that the singer “knows all about me and is a very nice lady.”Twenty Minutes, a transgender newsletter that circulated in the late 1980s and early 1990s, wrote about then 44-year-old Pirro in its August 1990 issue, pulled from a story in which the tabloid Star spoke to Pirro about his relationship with Parton.The newsletter item gained renewed traction on social media following Parton’s passing when it was shared by writer Gillian Branstetter, who works as a communications strategist for the American Civil Liberties Union but posts online in a personal capacity. Per Twenty Minutes, Parton was then being “chauffeured around Hollywood” by Pirro, whom the newsletter claims “had an operation to change from a woman into a man” — most likely language pulled directly from the Star article, though the contents of that issue were not immediately available for independent confirmation that it is a reprint.The cover of that particular issue of Star — dated July 10, 1990 — remains online, however. In one eBay listing, the headline reads: “Sex change shocker in Dolly’s limo,” with a subheadline stating: “Her driver is a man who used to be a woman.”The Twenty Minutes issue highlighting the Star article remains widely accessible through the Digital Transgender Archives, an online hub of materials meant to preserve trans history. That newsletter itself is housed in the Sexual Minorities Archives in Holyoke, Massachusetts, which also holds the research materials of late trans author and activist Leslie Feinberg.In quotations selected from Star, Pirro seems to suggest that Parton was a