An “infatuated” prison officer who carried out a secret sexual relationship with a convicted gang member — while smuggling contraband into the jail — has been sentenced to two and a half years behind bars.

Charlotte Winstanley, 27, was working at HMP Lindholme near Doncaster when she began a “substantial sexual relationship” with inmate Jabhari Blair, 30. The affair included explicit photos and videos, secret meetings inside the prison, and the illegal delivery of mobile phones, SIM cards, and other banned items.

The scandal was described by a judge as the worst case of its kind he had ever handled.

A Dangerous and Secret Affair

Sheffield Crown Court heard that Winstanley smuggled a mobile phone into the prison so she and Blair could communicate via WhatsApp and Snapchat. The pair exchanged dozens of intimate messages, including one in which Winstanley wrote:

“I love my job, but I love you more.”

Another message read:

“Life starts now, baby. Every sacrifice I make I do so I can be with you.”

Blair, who was jailed in 2014 for 12½ years due to his involvement in organized crime, reportedly told Winstanley he “couldn’t wait” to give her a baby.

The court was told the pair even referred to Mondays as their “date nights.” Prison CCTV captured them touching and then disappearing together into rooms while on duty.

Training Ignored, Rules Broken

Winstanley joined HMP Lindholme in October 2020 as an operational support officer and later became a prison officer. She had received full anti-corruption training — yet still pursued the relationship.

Judge Jeremy Richardson KC said:

“You knew it was wrong and against all the training you’d received — but you brazened it out and continued the corrupt affair.”

Despite suspicions from colleagues, Winstanley continued her relationship with Blair and even took screenshots of news articles detailing his serious crimes.

She went on to smuggle SIM cards into the prison and shared sensitive information with Blair, including:

• Prisoner movement details

• Healthcare information about other inmates

• Advance warning of a cell search

A Security Risk Inside the Prison

The court heard Blair told Winstanley he had people inside the prison who would protect her, claiming someone was ready to “fight immediately if necessary.”

Winstanley also developed a close relationship with Blair’s mother, who the judge said was “clearly aware” of the nature of the affair.

Sentencing

Winstanley admitted to misconduct in public office and transmitting an indecent photograph from inside the prison. She was sentenced to two and a half years in prison.

Blair pleaded guilty to possessing cannabis and a prohibited mobile phone and USB stick. He received an additional 13-month sentence.

Judge Richardson concluded:

“It is utterly clear that you both knew that what you were doing was unlawful and corrupt.”

The case stands as a stark reminder of how personal relationships behind bars can quickly turn into serious security threats — with devastating consequences for everyone involved.