A judge has heard details of what was described as one of the most serious cases of an inappropriate relationship between a prison officer and an inmate to come before the courts.
Proceedings at Sheffield Crown Court revealed that Charlotte Winstanley, 27, engaged in a “romantic and intimate” relationship with prisoner Jabhari Blair, 30, over a three-year period while working at HMP Lindholme, near Doncaster.
The court was told that Winstanley smuggled a mobile phone into the prison, enabling the pair to exchange intimate photos, videos, and frequent messages. Texts read out in court included one in which she wrote: “I’m literally praying to have your babies.”
Other messages referred to Mondays as their “date nights” and expressed long-term commitment, with Winstanley telling Blair that she loved him more than her job.
Prosecutor Aaron Dinnes said Winstanley acted as Blair’s “link to the outside”, helping him obtain items through online retailers and visiting his mother at her home. Investigators also found she passed on confidential information about prison searches, prisoner movements, and healthcare matters.
CCTV footage shown to the court captured the pair engaging in inappropriate physical contact and disappearing together into private rooms within the prison.
The judge was told that Blair belonged to an organised crime group and had previously been jailed for serious violent offences. Prosecutors said he promised Winstanley protection through his criminal contacts, further increasing the security risk posed by the relationship.
Judge Jeremy Richardson KC described the case as “arguably the worst” of its kind he had dealt with, citing the length of the relationship, the smuggling of contraband, and the breach of professional responsibility.
He said the conduct had seriously undermined prison security and public confidence in the justice system.
In mitigation, Winstanley’s defence said she had been young and emotionally inexperienced when she began working at the prison, and that Blair was her first serious relationship. Her lawyer described her lack of maturity as a “recipe for disaster”.
However, the judge noted that her training had included clear warnings about inappropriate relationships and corruption risks.
Winstanley has admitted misconduct in public office and transmitting images from inside a prison. Blair has admitted possessing cannabis and prohibited items, including a mobile phone and a USB stick.
Both defendants have been remanded in custody and are due to be sentenced at a later hearing.