Playboy rapist Simon Monteiro complains about mental health as legal battle hits rocky ground

The “playboy rapist” legal bid to get out from court-ordered supervision is on rocky ground as the convicted man complains about his mental health and misses crucial deadlines.

The infamous “playboy rapist” will have one last chance to free himself from court-ordered supervision after telling a court he’s caring for his sick dad and nursing a PTSD diagnosis.

It comes a week after he fronted court facing allegations of harassment against another woman in a new matter.

Monteiro, a former model and spiring actor, was jailed for more than a decade in 2009 after violently raping an ex-girlfriend.

His flashy lifestyle and boasts about dating celebrities including Mariah Carey earned him the nickname “the playboy rapist” when he was jailed for 12 years.

Monteiro walked out of prison in 2020 and was put on a five-year supervision order known as an ESO.

Simon Monteiro appears in Gosford court turning his camera on waiting media Tuesday 9th April 2019. He was dubbed the "playboy rapist"for sexual assault charges. Picture: Sue Graham

The sex offender has fought the supervision order since it was imposed and, last month, was warned he’d missed important deadlines.

Monteiro, on Monday, appeared before the NSW Court of Appeal to argue why his legal battle against the ESO should be allowed to continue.

Simon Monteiro appears in Gosford court turning his camera on waiting media Tuesday 9th April 2019. Picture: Sue Graham)

Justice Anthony Meagher noted that Monteiro’s appeal against the ESO was interrupted when the rapist breached the order dozens of times within a month of release in 2020 and ended up back in prison.

It meant Monteiro was filing handwritten documents and fighting the ESO from behind bars until his release in February this year.

Since then Monteiro has missed multiple crucial court dates without explanation.

Monteiro, on Monday, assured Justice Meagher he had applied for LegalAid, despite being rejected numerous times by the publicly funded lawyers and claimed he had assets in the United States.

He also said he was helping his elderly and unwell father but, as the judge noted, it was “not explored” how this has limited his capacity to fight his case.

Simon Monteiro says that he suffers from mental health and its affected his ability to be part of the proceedings.

“Mr Monteiro says that he suffers from a post-traumatic stress disorder which has affected his ability to prosecute the proceedings, either representing himself or, perhaps, in instructing lawyers,” Justice Meagher said in his judgment on Friday.

“The Court has no explanation as to why this evidence might not have been obtained (after earlier hearings).”

Justice Meagher handed Monteiro one final chance to get his case together.

“In this state of affairs, it seems to me that a way forward which has regard to the interests of both parties to the appeal is to give Mr Monteiro one further opportunity to get his appeal ready for hearing and heard,” he wrote.

The judge ordered that the appeal will fail if Monteiro does not file written documents by the hearing date of September 15, 2022.

Unusually, Judge Meagher said Monteiro had sent him an email at the end of Monday’s hearing but had not sent it to the lawyers for the government, his opponents in the case.

“The email contains allegations directed to judges or former judges of the Court,” Justice Meagher said.

“Depending on the circumstances, the making of those allegations, which address matters wholly irrelevant to any issue before the Court, would constitute a serious contempt of court on the part of Mr Monteiro.”

“Nothing more need be said.”

Justice Meagher is not the first magistrate or judge to take a dim view of Monteiro’s conduct in court – it’s not even the first time this month.

Monteiro, last Friday, quarrelled with Magistrate Peter Feather as he fronted a Local Court accused of harassing a woman over the phone.

Magistrate Feather muted Monteiro’s videolink to the court and punted him to the end of the busy court’s queue.

When Monteiro was allowed to speak again, 45 minutes later, he continued bickering about his alias “Simon Lowe”.

He insisted it is not an alias.

Monteiro is accused, in the Local Court matter, of using a mobile phone to harass the woman during a five-hour period on the evening of April 1 this year.

He told the court he would represent himself and call six witnesses in the hearing slated for February.

Monteiro is banned from Neutral Bay and must not contact the woman involved in the meantime.