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‘Playboy rapist’ a ‘psychopath’: court

Supplied Editorial Simon Monteiro
Simon Monteiro has been described as a ‘psychopath’ in court.

A notorious sex offender dubbed the “playboy rapist” has been described as a “psychopath” with a compulsion to lie as he fights to have his personal devices given back to him by police.

Simon Monteiro was handed a two-year jail sentence in June 2021 after he was convicted of breaching a five-year extended supervision order (ESO) imposed after he finished a 12-year sentence for raping and bashing a Sydney woman.

But Monteiro walked out of Cooma Correctional Centre early in February 2022 after successfully appealing the severity of the sentence.

He previously led a reportedly glamorous playboy lifestyle and boasted about having a relationship with Mariah Carey before he landed in prison.

Despite his criminal case being concluded, Monteiro returned to court in July and applied to have NSW Police return $6000 worth of laptops and phones seized during the breach in 2020.

The application has been opposed by the police commissioner, with barrister Nicholas Regener on Tuesday telling the court Monteiro can’t be believed, as he is diagnosed with “psychopathic traits”.

Supplied Editorial Simon Monteiro
Simon Monteiro was sentenced to 12 years in jail for aggravated sexual assault.

“Psychiatric evidence shows he has a compulsion to lie and he has had those psychopathic trains since before he was 15 years of age,” Mr Regener told the court.

“He has narcissist personality disorder and anything which he says really ought to be treated with, I’d say, a grain of salt, but perhaps it should be an entire shaker.”

Mr Regener told the court that Monteiro, who was not in court on Tuesday, had continuously said he had an intention to appeal his conviction for the ESO breach with the NSW Court of Criminal Appeal.

Police needed to keep the devices as evidence for future proceedings, Mr Regener said.

He told the court that Monteiro was not entitled to lawful possession of the devices as he continuously told police he was not the owner.

The court was also told that police had concerns Monteiro may contact women and witnesses, as the devices had their personal information.

“Police are worried he will make contact and harass these people,” Mr Regener said.

“Those devices ought to be forensically wiped clean so the applicant is unable to retrieve that information … the only way to obliterate that data so it can never be recovered is to destroy those devices.”

Monteiro previously took to the witness stand and told the court “harassment by police” had destroyed his relationship and swore he was the sole owner of the devices.

Supplied Editorial Simon Monteiro
Monteiro in his younger years lived a playboy lifestyle.

Richard Cummins, representing Monteiro, told the court that police holding onto the items was “extremely spiteful”.

Mr Cummins told the court that his client had been compliant with the ESO and said there was a rare chance he would appeal his conviction.

“The computer and the phones are sitting and gathering dust, there’s no need for it to be in police possession,” Mr Cummins said.

“It is very pedantic and petty, to say the least, to keep these items just gathering dust … there are personal photographs of him and his partner at the time he wishes to have back.”

Magistrate Daniel Covington told the court that Monteiro gave evidence he was “agitating a CCA appeal” for both the ESO and the charges relating to the breach.

He said there were two main circumstances – the items are yet to undergo formal analysis with the forensic unit at NSW Police, and Monteiro gave sworn evidence he wished to appeal his convictions.

“He wishes to agitate both the unwinding of the ESO or have it set aside,” the magistrate said.

“Further, he wishes to change his plea or traverse his plea and have the matter considered by way of a retrial … I’m not saying it will be successful, but it’s certainly his intention.”

Mr Covington said the discretion fell in favour of refusing the application, as they were two “significant factors”.

He said the application would have failed “in any event” and refused it.

The magistrate also granted costs, meaning Monteiro has to pay the police commissioner’s legal costs.