John Pilley

Silhouette image via Wikimedia Commons

John / Jane Anne Pilley, a violent male who identifies as a trans woman, was sentenced to life imprisonment for the attempted murder and kidnapping of a female taxi driver Linda Charlesworth, in 1981. Pilley became the first prisoner in England and Wales to undergo gender reassignment surgery when he had an orchiectomy (surgical removal of testicles) at the age of 46 in April 1999.

Having taken hormones for seven years and developed breasts, Pilley’s legal case successfully argued it was unfair of the Prison Service to block his demands for genital surgery and  “leave him in the limbo of being part-man and part-woman.” Following the operation, Pilley was reportedly transferred to women’s prison HMP Holloway. 

Pilley created a precedent in 1999 for at least five other prisoners seeking sex-change operations and pursuing legal cases against the Prison Service, including Philip Taplin, Matthew Richardson who murdered a woman, double murderer Douglas Wakefield and armed robber David Cross.

Pilley subsequently decided to reverse the operation to identify as a man again and it was reported he was waiting to have this second operation on the NHS in 2006. The Metro reported that after spending 10 years identifying as a trans woman, Pilley had a second operation, took hormone treatments and was reintroduced to the male prison estate in spring 2018.

See also

Media reports:

The Times  archive

The Independent archive

Evening Standard 13.03.99 archive