A 32-year-old prosecutor faces serious charges after allegations surface of intimate relationships with multiple prison inmates and unauthorized access to hundreds of confidential files.

Alleged Relationships with Inmates

Vanessa O’Bryan, a solicitor with the New South Wales Office of the Director of Public Prosecutions (DPP), allegedly engaged in a romantic relationship with convicted gangland killer Joshua Baines. Baines serves a 27-year sentence for his involvement in the 2016 murder of crime figure Pasquale Barbaro in Sydney’s Earlwood suburb. O’Bryan previously represented Baines as a criminal defense lawyer.

Authorities claim O’Bryan maintained hundreds of conversations with Baines between May 8, 2023, and January 16, 2025, aimed at facilitating intimate sexual relations. A police prosecutor stated in court that O’Bryan had no legitimate reason as a DPP solicitor to contact inmates.

“She’s not only willing to have sexual relationships with inmates, but also compromise police investigations as a result of those relationships,” the prosecutor said. “Police don’t know what the actual impact of her accessing the records is because they are still investigating.”

O’Bryan also allegedly had an intimate relationship with inmate Terry Sampson. She reportedly alerted police after receiving abusive text messages from Sampson’s then-girlfriend, Sharna Cain. One message read: “I swear you and Terry aren’t getting away with this hahaha big lawyer I’m coming for you.”

Cain pleaded guilty to intimidation and received a 12-month community correction order. During a three-way call involving O’Bryan, Cain, and Sampson, O’Bryan made comments suggesting a sexualized relationship. She sent Cain a selfie of a shirtless Sampson captioned “I love you so much Vanessa” to confirm the relationship.

Unauthorized Access to Confidential Files

Police documents allege O’Bryan improperly accessed 1,439 pages related to 284 criminal matters with which she had no connection. “The accused is a DPP solicitor and former defense solicitor who has had access to high-level criminals on a professional and personal level,” the documents state. “The extent of the impact of the information that she has provided to these persons is not known and is potentially extremely damaging to other court matters and/or the safety of individuals.”

Legal Proceedings and Bail

O’Bryan was arrested in November 2025 and initially charged with misconduct in public office, illegal access to restricted data, and hindering evidence. She received police bail but later faced remand custody after additional charges of benefiting from a criminal group and concealing crime proceeds.

She has since been granted bail following months on remand. On Friday, in the New South Wales Supreme Court, Justice Sarah McNaughton lifted suppression orders on the case. “There is a higher public interest in open justice where a solicitor has been charged with serious criminal offences,” McNaughton ruled.