Trinity Grammar School teacher sentenced for sending explicit messages to 13yo girl

By day he was a teacher at one of Sydney’s elite schools. By night he sent explicit messages online to who he thought was a 13-year-old girl.

A former senior teacher at one of Sydney’s most elite private schools has avoided jail for sending sexual messages to who he thought was a 13-year-old girl.

Alexander David Simpson, who taught at boys’ school Trinity Grammar in the city’s inner west, was on Friday sentenced to 24 months imprisonment but was released immediately under a recognisance order.

Simpson was arrested in his crisp school suit in front of students last August after he fell for a trap police set in an online chatroom the teacher used to “escape the stresses” of life.

Alexander David Simpson (right) was working at an elite boys’ school at the time of the offences. Picture: Adam Yip

The 40-year-old was again suited when he appeared before the Downing Centre District Court via video link this week having pleaded guilty to using the internet to send indecent material to a person under 16 and soliciting child abuse material.

Judge Leonie Flannery said in sentencing Simpson that such crimes “exploit the vulnerability of youth and inappropriately sexualise young people before they are able to protect themselves”.

Judge Flannery, however, decided not to send him to jail. She found he was unlikely to reoffend after hearing he had thrown himself into rehabilitation and was deeply remorseful.

The court heard the vile messages Simpson sent the girl – who was actually an undercover cop – saying he was a “horny old man” and made persistent requests for photos.

Alexander Simpson said he was ashamed of the messages.

Using the name ‘Sydneyman’, the man trusted with forging young minds exchanged messages with the online persona between August 17 and 26, 2020 via the chatroom chatiw, Skype and email.

Their first conversation began with talk about how the teen was struggling with her homework and Simpson revealed he was a teacher.

“OMG I hope you don’t teach at my school LOL,” the girl wrote.

“LOL would you flirt with me if I did?… sorry that was weird,” he replied.

He asked her age and she replied that she was 13. “So… do you like older men?.. but I’m guessing you’re an innocent young school girl,” Simpson replied.

The man would soon push their conversation into even more sordid territory.

Simpson was arrested at work at Trinity Grammar’s Summer Hill campus.

He asked her if she was a virgin and if she had been with a 40-year-old man.

She said he sounded like a “nice” man but he replied: “Nah I’m just a horny old man.”

On August 18 the girl asked if they could move their conversation to Skype because her mother monitored her chat history.

He agreed, and on August 24, Simpson sent the girl a photo of himself fully clothed and another showing his erect penis.

“Can you send me a selfie?” he asked

He received a photo of a girl and replied: “You have a great smile although I can’t get my eyes off your t**s. Lol sorry.”

Simpson kept asking for photos of the girl’s breasts, which culminated in him receiving a picture of a girl in a bra.

The 40-year-old taught English at the school.

She told him her parents had separated at a young age and Simpson hypothesised the teen was “craving male attention”.

“And if I ask for a pic you should be flattered it’s because I want to see more of you,” he said.

“I also like it when you do what you are told.”

When arrested on August 27 he told police he never intended on meeting with the girl and insisted he didn’t believe she was actually 13, as the chatroom he met her on was for over 18s.

But he admitted he had never tried to confirm her age and said he was ashamed of the messages he sent.

He served eight days on remand before being released on strict bail conditions, which he has complied with.

Judge Flannery said Simpson’s fleeting time in custody had been onerous. Picture: Adam Yip

Giving evidence in court on August 5, 2021, Simpson broke down: “If there was a chance (the child) was actually who they presented as that was the very person in every other aspect of my life I was trying to protect, teach and help.”

The court was told that he was married with children and was the sole carer for his wife, who had a permanent disability.

His wife told the court that he was a “fantastic husband” who had gained a better outlook on life since his arrest last year.

Judge Flannery found full-time custody would be more onerous on Simpson due to the “anguish at not being able to care for his wife and children”.

Under the recognisance order he must be of good behaviour, not travel interstate, be monitored by corrective services and continue his treatment with a psychologist.