Douglas Wakefield

Douglas/Tai Wakefield (aka Tai Pilley and Dee Wakefield), a violent male who identifies as a trans woman, was convicted of the murder of a male relative (Wakefield’s uncle, Derek Wakefield) in 1974 and subsequently sentenced to life in prison. Wakefield brutally strangled the victim, beating him with a hammer and stabbing him 48 times with a garden fork in Gipton, Leeds.

In 1978, Wakefield strangled fellow prisoner Brian Peake with a shoelace, then stabbed and beat him to death in the psychiatric wing of HMP Parkhurst. Wakefield also twice took prison officers hostage and tried to kill one of them, and clocked up more than 1,000 hours in solitary confinement.

After having gender reassignment surgery in prison, Wakefield was transferred to the women’s closed-category prison HMP New Hall and in 2010 and 2013, then aged 61 and 63, was linked to relationships with female prisoners, one of whom was transferred out of the prison when their relationship broke down as Wakefield was sexually pursuing yet another female prisoner.

It’s unknown if the adoption of the surname Pilley (as reported in some media articles) relates to a relationship with John Pilley (another violent male who identifies as a trans woman) or whether the newspapers have muddled up the two trans-identified male prisoners. Certainly, John Pilley’s case created the legal precedent in 1999 for at least five other prisoners (including Wakefield) to have gender reassignment operations in prison. 

In 1996, Wakefield’s lawyer claimed in the Daily Telegraph that the killings were directly related to Wakefield being transgender. She said: “Her [Wakefield’s] uncle was taunting her about her transsexual situation when she snapped.” As if that would somehow be an explanation or justification for strangling Derek Wakefield, beating him with a hammer and stabbing him 48 times until he was dead.

Photo via Gender Variance Who’s Who

Media reports

Yorkshire Evening Post  archive

Daily Star  archive

Stoke Sentinel  archive

The Independent  archive

Daily Telegraph 12.11.96 archive

The Courier Mail