A disgraced prison officer who had an illicit affair with a convicted gang member and told him she was ‘literally praying’ to have his baby has been released after serving just six months of a two-and-a-half year sentence.
Charlotte Winstanley, 28, flaunted her new-found freedom on TikTok after walking free from HMP Drake Hall in Staffordshire in August.
The shamed former guard was jailed in February after she admitted misconduct in a public office over her forbidden relationship with violent inmate Jabhari Blair, 30.
Winstanley had been working as an entry-level officer at HMP Lindholme when she embarked on an affair, with arranged secret trysts inside locked prison offices.
The pair swapped explicit WhatsApp and Snapchat messages, in which Winstanley told him she was ‘literally praying’ to have his baby.
Blair, serving 12-and-a-half years for stabbing a man during a mass brawl, meanwhile wrote of her ‘sexy lips’ and ‘little booty’, describing how ‘your body used to respond to my touch’.
Disgraced prison officer Charlotte Winstanley, 28, has walked free from prison after serving just six months of her two-and-a-half-year sentence for having an illicit affair with a prisoner
Winstanley flaunted her new-found freedom on TikTok after walking free from HMP Drake Hall in Staffordshire in August
The shamed former guard, seen smiling with friends and family on her release, was jailed in February after she admitted misconduct in a public office
Winstanley admitted her forbidden relationship with violent inmate Jabhari Blair, 30
Winstanley was jailed at Sheffield Crown Court where a judge described her case as worst of its kind he had dealt with ‘by some considerable margin’.
Yet despite being handed a 30-month sentence, Winstanley returned to her home in Stainforth, near Doncaster, in mid-August having served barely half a year.
Announcing her return on social media last month, Winstanley posted on TikTok: ‘Took a couple months off I’m still good over here though.’
She later uploaded a black-and-white video showing the moment she left prison to be greeted by family and friends, who showered her with confetti.
Alongside the clip, Winstanley wrote: ‘My sister always told me ‘this too shall pass’ and oh it did.
‘You never feel true love and adoration until the day you walk out the gate and restart your life at 28! It turns out life really does go on, no matter how much you mess up or how many times you fall down.
She added: ‘Love conquers all and always will’.
Aged 22, Winstanley was tasked with maintaining order among the 900 inmates inside HMP Lindholme, a Category C jail near Wetherby in West Yorkshire.
Yet Sheffield Crown Court heard how she struck up a relationship with Blair while monitoring him on the prison’s J Wing in August 2022.
She bragged to a friend about having ‘sex daily’ and declared it ‘the best she had ever had’.
In one graphic message Winstanley crudely told how having been with Blair she ‘would now never go back’.
Their covert relationship continued for around three years, prosecutors said, with the shamed officer continuing the romance even after she was suspended from her post.
Passing sentence, 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.’
The court heard how Winstanley was seen leading Blair into a locked office at the prison, where the pair remained alone for three minutes.
On another occasion she arrived an hour early for work and took Blair into an office before emerging 14 minutes later.
Judge Richardson told Winstanley: ‘It is utterly clear that you both knew that what was happening was unlawful and corrupt.’
Winstanley’s phone was seized in November 2022 after prison bosses became concerned she was taking contraband inside.
Searches of the device revealed Blair directing her to buy items on his behalf, including SIM cards and SD cards.
At one point, he even directed her to the Argos website so he could choose what he wanted brought into prison.
Winstanley also met with Blair’s mother outside prison and shared confidential information, including sensitive plans to transfer him to another jail.
She also furnished Blair with confidential intelligence concerning other inmates’ medical records and a search carried out on his own cell.
Judge Richardson told her: ‘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.’
Even after being suspended from the Prison Service in November 2022, Winstanley registered to visit Blair after he was transferred to HMP Ranby in Nottinghamshire.
During one video call she was recorded telling Blair she ‘hoped’ she was pregnant with his baby and professing her love for him.
She also created a fake email account under the name ‘Debbie Pendalton’ so she could continue contacting him.
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.’
Winstanley’s barrister Khadim Al-Hassan said she was ‘deeply remorseful’, adding that the relationship was her first since school aged 15.
He said: ‘If there was ever a job that required an age of maturity requirement, this is one.’
Blair, originally from Leeds, West Yorkshire, was jailed in 2014 after stabbing a man during a gang brawl in Bradford. It is believed he remains in prison.
It is unclear exactly how Winstanley has come to be released on licence having served just a fifth of her sentence.
The Mail has approached the Ministry of Justice for clarification.
Her freedom, however, comes ahead of Labour’s latest early release scheme which will see automatic release dates for tens of thousands of prisoners brought forward.
Under the scheme, which will take effect next month, some criminals who faced serving two-thirds of their sentence before being released will now be let out after only half their term.
Less serious offenders will be released after serving just a third of their sentence in a bid to ease prison overcrowding.
Around 700 eligible offenders will leave jails in England and Wales on October 1 and 2,550 will have been released by the end of the year.
Winstanley bragged to a friend about having ‘sex daily’, declaring it ‘the best she had ever had’
Blair, originally from Leeds, West Yorks, was jailed in 2014 after stabbing a man during a gang brawl in Bradford. It is believed he remains in prison
During one video call Winstanley was recorded telling Blair she ‘hoped’ she was pregnant with his baby and professing her love for him
Even after being suspended from the Prison Service in November 2022, Winstanley registered to visit Blair after he was transferred to HMP Ranby in Nottinghamshire
Prime Minister Andy Burnham was forced to U-turn on plans to release those convicted of manslaughter early after it emerged two killers of PC Andrew Harper would be eligible for freedom.
Jessie Cole and Albert Bowers were among three teenagers jailed over the death of the Thames Valley officer, 28, who died in August 2019 when he was dragged by a car.
More than one million people signed a petition calling for the pair to remain behind bars.
At the weekend, Mr Burnham excluded anyone convicted of unlawful killing from the scheme, saying extra prison space would instead be created by deporting foreign prisoners.
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