Case Studies: 

‘Alex Stewart’ (AKA Alan Baker) & Sophie Eastwood (AKA Daniel Eastwood)
Karen White
Karen White

Alan Baker was convicted of murder in 2013 at High Court in Dunbarton after he killed a man he had met through an online gay dating service by stabbing him in the chest at least 16 times.  He was sentenced to life imprisonment.  At the trial it was revealed that Baker had a history of domestic violence, inflicting abuse on five other male partners (Keith McLeod, Daily Record, 14 February 2018).

By 2018, Baker had ‘transitioned’, had changed his name to Alex Stewart and was imprisoned in the female estate at HMP Greenock.  Although he had not had any ‘reassignment’ surgery, he was reported to be ‘living as a woman’.  His ‘womanly’ activities included working in the prison hair salon, learning about make-up application, showering with the female inmates and winning the prison’s coveted Miss Fitness trophy.  A prison source elaborated, “The rest of them shouldn’t have bothered even entering.  It was surreal.  Everybody knew it wasn’t very fair, but nobody was allowed to say it.  The women inmates have had to accept that Stewart is being allowed to live as a woman, despite not having had surgery.  That means she is in the showers at the same time as other inmates, which some have found quite awkward (sic).” (Keith McLeod, Daily Record, 14 February 2018)

As well as the Miss Fitness trophy, Stewart received a goodie bag that included high value items: chocolate, crisps, snacks, coffee, tea, juice, soap and toiletries.  The source explained, “That kind of stuff in jail is real currency.  You can use it to exchange for anything you want.” (Keith McLeod, Daily Record, 14 February 2018)

2018 was a busy year for Stewart.  As well as showering with women and demonstrating his sporting prowess, he began a relationship with fellow ‘transitioner’, Daniel Eastwood, AKA Sophie.  


Eastwood and Stewart have much in common: they are both males serving time in a women’s prison, both received life sentences for murder, neither have had any surgery.  At HMP Greenock their love bloomed.  A prison source stated, with what we can only hope was intentional irony, “Alex has always said that her preference is men.  But she did say she would consider going with a woman and it looks like Eastwood has fitted the bill (sic).”  However, their ardour increased and they ended up having sex in the grounds of HMP Greenock in front of the female inmates.  The authorities intervened and Eastwood was transferred to the women’s section at HMP Polmont (Mark Henry, The Scottish Sun, 7 May 2018).  Stewart remained at HMP Greenock.