An ‘infatuated’ prison officer who embarked on a secret sexual relationship with a convicted gangster has been jailed for two-and-half years after a judge branded the case one of the worst of its kind.
Charlotte Winstanley, 27, began the forbidden affair with inmate Jabhari Blair, 30, while working at HMP Lindholme, South Yorkshire.
A court heard how Winstanley had illicit trysts with Blair on prison grounds and sent him messages saying she was ‘literally praying’ to have his baby. The couple also had a ‘date night’ on Mondays at the prison.
Their covert relationship continued for around three years, with the shamed officer continuing the romance even after she was suspended from her post.
Winstanley is the latest in a string of young female prison officers to be jailed for engaging in inappropriate relationships with inmates.
She was told by a judge at Sheffield Crown Court that the extent of her offending was ‘by far the worst’ he had dealt with.
Jeremy Richardson, KC, the Recorder of Sheffield, said: ‘Regrettably I have dealt with several cases of woman prison officers having intimate relationships with prisoners and occasionally taking in to the prison various prohibited items.
‘All have been imprisoned. ‘By some considerable margin this case is by far the worst with which I have had to deal.
‘It is an exceptionally serious case of its kind.’
Charlotte Winstanley was jailed for two-and-a-half years for the illicit thing with a prison inmate
The court heard she was infatuated with Jabhari Blair who was serving a 13-year sentence
Winstanley became besotted with Blair, a member of a crime gang serving 12-and-a-half years for stabbing a man, while monitoring him on the prison’s J Wing in August 2022.
The pair swapped explicit WhatsApp and Snapchat messages on a phone smuggled in by the guard in which the couple professed their love.
In one exchange, Blair said he wanted to give her a ‘beautiful baby’, prompting Winstanley to reply: ‘I’m literally praying to have your baby.’
She also bragged to a colleague that she was ‘having sex daily and it was the best sex she ever had.’
Judge Richardson said of the explicit messages: ‘It is unnecessary for me to sully these sentencing remarks with the various intimate observations that were being made.
‘What is important is that it was clear between the two of you that you were regarding Monday evenings as “date night”.
‘You exchanged explicit photos and videos between each other, you also spoke about deleting messages in order to eliminate any possibility of anyone being able to trace these messages.
‘It is utterly clear that you both knew that what was happening was unlawful and corrupt.’
Winstanley, 27, pictured outside Doncaster Magistrates Court following an earlier hearing
The court heard how Winstanley was seen leading Blair into a locked office at the category-C prison, where they remained alone for three minutes.
On another occasion, she arrived an hour early for work and took Blair into an office before her shift began.
The pair emerged from the room 14 minutes later, the court heard. Winstanley’s phone was seized in November 2022 following concerns from prison bosses that she was ferrying contraband into prison.
Searches revealed Blair directing Winstanley to buy items on his behalf, including SIM cards and SD cards, and even pointing her to the Argos website to select what he wanted smuggled inside.
Winstanley also met with Blair’s mother outside prison and shared confidential information, including sensitive plans to move him to another jail.
She also furnished Blair with confidential intelligence concerning other inmates’ medical records and a raid carried out on his own cell.
Judge Richardson told Winstanley: ‘You knew this was comprehensibly wrong and against all the training you had received.
‘Not only was there a sexual relationship which endured for a prolonged period but you took in items which were prohibited and sent a photo of the interior of the prison outside the prison.
‘The prison authorities also had some suspicions about your conduct. Consequently, meetings were held with you where it would have been possible to reveal any pressure which was being placed upon you.
‘But instead, you brazened it out and continued your corrupt affair.’
After being suspended from the prison service in November 2022, Winstanley registered to visit Blair at HMP Ranby in Nottinghamshire.
In one video call, she was recorded telling Blair she ‘hoped’ she was pregnant with his baby and professed her love.
Winstanley also created a fake email account under the name ‘Debbie Embleton’ to continue to contact her lover.
In one graphic message, she told him: ‘Just thinking about it – I miss it.’ In another she wrote: ‘Every sacrifice I made I did it so I could be with you. I love my job but I love you more.’
Blair meanwhile responded talking of her ‘sexy lips’ and ‘lil booty’. Judge Richardson said: ‘Those messages depict explicit sexual relations between you and him and there are a variety of messages that reveal the level of intimacy.
‘There can be no doubt whatsoever you were having a substantial sexual relationship with him whilst in prison.
‘You were, it would seem, comprehensively infatuated with him.’
The court heard how Winstanley spoke about her ‘boyfriend’ with fellow officer Morgan Farr Varney, who had also recently joined the prison service.
Varney was herself jailed for 10 months last year after also having a relationship with an inmate at HMP Lindholme.
Winstanley, of Doncaster, South Yorkshire, admitted misconduct in a public office.
She also admitted sending a photograph from inside the prison. Her barrister Khadim Al-Hassan said she was ‘deeply remorseful for her behaviour and her actions’.
Judge Richardson told Winstanley: ‘Once a prison officer has succumbed to corruption, by any form of impropriety, it is a state of affairs from which it is bordering impossible to retreat.
‘Here was not a case of a young woman facing a kaleidoscope of competing loyalties.
‘It was a case of right and wrong. In your case, Winstanley, you chose the wrong path and knowingly did so.
‘The corruption went from bad to worse and lasted for a protracted period.’
Blair, originally from Leeds, West Yorks, was jailed in 2014 after stabbing a man during a gang brawl in Bradford and remains in prison.
He has previous convictions including robbery, violent disorder, wounding with intent, firearm possession and assaulting police officers.
Blair was jailed for 13 months after admitting possessing cannabis, a phone and a USB stick found in his cell. Their sentences were reduced to reflect delays in bringing the prosecution.
