Jail for Lindholme prison officer over 'date nights' with inmate in 'worst corruption case' judge has seen
A disgraced prisoner officer who held “Monday date nights” with her jailed boyfriend and “prayed to have his babies” has been jailed.
The judge who sentenced the prison guard said it was “the worst corruption case” he had ever seen.
Charlotte Winstanley, of Coronation Road, Doncaster, threw herself into a sexual relationship with gang member Jabhari Blair, 30, who is serving a 12-year sentence at HMP Lindholme for wounding, robbery and possessing firearms.
But the 27-year-old prison officer - who was 22 when she began her job - seemingly saw the best in Blair, supplying him a mobile phone so she could swap messages about their next illicit meet up inside.


She also smuggled him cannabis, disappeared into private offices with him while on duty, warned him about upcoming searches of his cell, and shared details about other inmates’ health conditions.
“This is an exceptionally serious case of corruption,” said The Recorder of Sheffield His Honour Judge Jeremy Richardson KC at the pair’s sentencing today (February 2).
“Regrettably, I have dealt with several cases of women prison officers having intimate relationships in prison - by some considerable margin, this is by far the worst.”
A packed public gallery made up of Winstanley’s friends and family observed the sentencing hearing as the prison officer, who appeared in a maroon tracksuit, quietly sobbed as details of her offending were read out.
Winstanley and Blair began their relationship shortly after she started at HMP Lindholme in South Yorkshire in October 2020.
She became his link to the outside, smuggling him a phone and even taking instructions of items he wanted from Argos and brought into prison.
The court heard Winstanley was “infatuated” with the gang member as they swapped hundreds of intimate, sexual messages. Texts to him included: “Life starts now, baby. Every sacrifice I make I do so I can be with you.”
Others included “I love my job but I love you more,” and one which read: “I’m literally praying to have your babies.”


The court heard Winstanley received anti-corruption training, and had two meetings with prison officials were she could disclose if she was under any undue pressure from inmates. She said nothing.
CCTV later used in evidence showed the pair acting intimately on staircases and corridors around prison, including several occasions of disappearing into cells and offices together.
She provided him confidential information about prisoners across HMP Lindholme, such as transfers and even medical conditions. She warned him about upcoming searches of his cell, then pulled him aside to speak privately with him when they were over. She also sent a photo from inside the prison to an unnamed party.
Meanwhile, Blair told his prison officer girlfriend he had used his contacts to ensure she was “protected” while on duty, with other inmates “ready to fight immediately” if necessary.
She even became close with Blair’s mother.
However, anti-corruption officers at HMP Lindholme grew wise to Winstansley and Blair’s relationship, and she was arrested in November 2022.
She later pleaded guilty to misconduct in a public office and transmitting a photograph from inside a prison. Blair also pleaded guilty to possessing cannabis and prohibited items, namely a phone and a USB stick.
The court heard Winstanley is today “filled with remorse” about the affair and accepts full responsibility.
Judge Richardson noted she was young and immature when she began the relationship, and accepted a letter she wrote where she detailed her desire to “focus on the future.”
But, in sentencing, the judge said: “This case is a very serious example of its kind.
“It is a case of right or wrong - and, I’m afraid to say in your case, you chose the wrong path and knowingly did so.
“The corruption went from bad to worse.”
Blair, who is serving a 12-year sentence following a recall to prison, was told he had “personally corrupted a prison officer” in a way that was “about as bad as it gets.”
Winstanley was sentenced to two-and-a-half years in prison, with Judge Richardson remarking: “I’m very conscious that prison for you as a former prison officer will fall very hard on you.”
Blair received a 13-month prison sentence consecutive to his 12-year sentence.
