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Forensic psychiatrists who assessed convicted “playboy rapist” Simon Monteiro warned he was a deceitful, aggressive psychopath with no remorse and who was “well above the average risk of reoffending”.
Monteiro, a serial abuser, former model and aspiring actor from Sydney’s eastern suburbs, was sentenced in 2009 to 12 years in prison for rape and assault of a former girlfriend.
His denials, personality disorder and rejection of authority presented a “far more ominous scenario” than sex offenders who simply lacked insight into their offending, one psychiatrist warned when assessing his suitability for release in 2020.
Years later, Monteiro will on Thursday face a Sydney court charged with stalking and attempted stalking of a woman, and failing to comply with the conditions of his release. In July, he will also face a District Court trial on five counts of failing to comply with his supervision orders.
The NSW government has sought to tighten bail laws and increase punishments for domestic violence offences in response to the domestic violence murder of Molly Ticehurst.
The ‘playboy’ with a sinister reputation
Monteiro had a reputation for abuse, but also a reputation for worming his way out of convictions.
Between 1997 and his 2009 imprisonment, police received scores of complaints from women who said they had been in an abusive relationship with Monteiro and, when they broke off contact with him, faced stalking, harassment, sexual assault or other violence, court records show.
In 2000, he was convicted of threatening a witness after blackmailing a model with whom he had secretly filmed himself having sex. In the same year, he faced a rape charge, which resulted in a hung jury.
The following year, he was given a suspended sentence for assaulting his ex-partner, showing up at her house, and throwing a rock through her window. He was given a suspended sentence and placed on a two-year bond.
Monteiro was charged with aggravated break and enter and kidnapping an ex-partner in 2005, and issued an apprehended violence order, which he breached numerous times. His trial was withdrawn at his ex-partner’s request.
He then changed his name from Simon Lowe to Bonito Monteiro, telling women it was Portuguese for “beautiful hunter” to distance himself from his reputation.
In 2008, his then-partner connected the dots, unmasking him as Monteiro. He raped and assaulted her. When she went to the police, he returned to the home they had shared, dumping her clothes and discarding one shoe of every pair in her collection.
He was found guilty in 2009 and sentenced to 12 years in prison.
Risk to the community
In custody, Monteiro assaulted prison staff and threatened to rape a guard’s wife. He was denied parole in 2015 and 2016 before being released in 2018.
More than 30,000 people signed a petition to keep him behind bars and to reform the parole system “to ensure that offenders, who are not truly reformed and continue to pose a risk to the community, are not released, even if their sentence is up”.
However, his parole was short-lived: he was returned to jail when it was revoked 11 days later for threatening his former barrister.
Following his release in 2020, Monteiro was placed on strict supervision orders, during which the two psychiatrists assessed him as being at high risk of committing further violent and sexual offences. The supervision orders were extended to February 2027 due to continual breaches and periods of incarceration.
Twenty-six orders were made, including wearing an ankle bracelet, a curfew, a requirement to give the name and contact details of anyone staying overnight and not to be able to spend the night elsewhere, to inform the departmental supervising officer within 24 hours of anyone he had a sexual intimate relationship with, not to change his name and to provide all logins to any internet sites he visited.
Those warnings have become reality several times since then. In 2021, he was convicted of eight breaches of his supervision order and sentenced to two years and eight months in prison. This sentence was reduced on appeal, and he was released in February 2022 with the same 26 supervision conditions in place.
In 2024, several of his supervision conditions were revoked, including the need to wear an ankle monitor.
But a year later, Monteiro allegedly began reoffending. In December, he was charged with two domestic violence intimidation offences, along with half a dozen breaches of his supervision orders. In February this year, he was charged with three more bail and supervision breaches. He has not been convicted of these charges, and they are before the court.
A vexatious prisoner
Monteiro has lodged scores of appeals against his convictions, sentencing, supervision orders and prison conditions, sending him broke and forcing him to apply to the courts for pro bono legal representation.
In 2015, he unsuccessfully attempted to challenge his prison treatment, arguing against being charged photocopying fees, attempting to change the correctional centre he was in, and arguing against the use of prison trucks and prison vans, claiming he should be transported only in sedans, station wagons or four-wheel drives.
During his second jail stint in 2021, he unsuccessfully fought decisions including refusing him $200 gel sneakers or orthopedic shoes, a sleep apnoea machine and treatment, aviation textbooks and access to TAFE courses; not reducing him to minimum security categorisation and issuing an extreme threat inmate status and “forcing” him to be associated with other prisoners, which would endanger his physical and mental health. The case was dismissed with costs to be paid by Monteiro.
In his cases, he used “colourful” language to fight his case, judges have noted, including “making statements which were offensive to, and defamatory of, present and former Judges of this Court”.
Reforms introduced by the NSW government include making it harder for those charged with serious domestic violence offences to get bail and fitting those released with electronic monitoring bracelets. The non-parole period for intimate partner homicide was also increased to 25 years.
Anyone needing support can contact National Sexual Assault, Domestic and Family Violence Counselling Service 1800RESPECT (1800 737 732); Lifeline 131 114; Beyond Blue 1300 224 636.
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