Prison guard who bragged about 'sex daily' with gang member freed early
Prison guard who bragged about 'sex daily' with gang member freed

Charlotte Winstanley, the former prison guard jailed for an illicit affair with a gang member, has been released early after serving six months of her two-and-a-half year sentence.

The 28-year-old was spotted walking out of HMP Drake Hall in Staffordshire last month, appearing cheerful with family members and lifting up a child for a cuddle in footage shared on TikTok.

Boasted about 'daily sex'

Winstanley was jailed in February after admitting misconduct in public office over her relationship with Jabhari Blair, 30, a convicted gang member. Her role as a guard at HMP Lindholme, near Doncaster, had included maintaining order among the 900 inmates.

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Sheffield Crown Court heard how she began the illegal relationship with Blair while monitoring him in the Category C jail in August 2022. She bragged to a pal about having "sex daily" with Blair and claimed it was "the best she’d ever had."

Messages and gifts

The pair also swapped x-rated WhatsApp and Snapchat messages, in which Winstanley told him she was "literally praying" to have his baby. The relationship lasted around three months, and she continued it even after being suspended from her post.

Her phone was seized, and searches revealed Blair directing her to buy items on his behalf, including SIM cards and SD cards. He even told her to go to the Argos website so he could decide what he wanted her to bring into prison. Winstanley also met Blair's mother outside jail and shared confidential information, including plans to transfer him to another jail.

Sentence and release

Passing sentence, Jeremy Richardson, KC, the Recorder of Sheffield, said: "Regrettably I have dealt with several cases of women prison officers having intimate relationships with prisoners and occasionally taking into 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."

At the time, Blair was serving a 12-year sentence for stabbing a rival in a mass brawl in Bradford. Once Winstanley was suspended in November 2022, Blair was transferred to another jail. In her TikTok video, Winstanley wrote: "Took a couple months off I'm still good over here though," and added: "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!"

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