
Barrister who inspired TV lawyer banned for sexual harassment
A NSW barrister who inspired the flirtatious main character of TV show Rake has been found guilty of sexual harassment. Seventy-five-old Charles Waterstreet had preyed on three female colleagues significantly younger than him.
He tried to blame his misconduct on his bipolar disorder, which included showing a drawing of his “beautiful” penis to one of the women. Mr Waterstreet copped a one-year ban from practicing law after being found guilty by the NSW Civil and Administrative Tribunal.
In this article, we detail the sexual harassment Mr Waterstreet subjected his victims to and the tribunal’s ruling. We also look at the case of a NSW solicitor who was ordered to pay his victim $170,000. The solicitor had sexually harassed a paralegal by bombarding her with romantic emails and entering her hotel room in his underwear.
‘Politically incorrect’ barrister banned for sexual harassment
Mr Waterstreet’s harassment took place between 2014 and 2019. One of the victims was a law student still at university, who claimed that Mr Waterstreet had watched a pornographic video near her. She also alleged that he had once said to her that he wanted to “rub” a client’s partner “all over.”
The student also alleged that he had drawn a picture of a penis, and while showing it to her, said that it was a “drawing of my beautiful penis.”

A second victim, a 24-year-old legal secretary, said that she was sexually harassed by Mr Waterstreet in an elevator. She said that there were three other men in the elevator, and when a fourth entered, Mr Waterstreet asked her “which of the four of us would you prefer?”
A woman later entered the elevator when it stopped at another floor. The secretary claimed that Mr Waterstreet then said, “I didn’t mean to be discriminatory earlier, which of the five of us would you prefer.”
A third victim, another law student, claimed that Mr Waterstreet showed her a “black vibrating sex toy” during a job interview, which left her “sick in the stomach.” She also alleged that he said he had the “biggest c*ck in Australia.” The student also claimed that Mr Waterstreet said to her that “female orgasms were more volcanic and far more powerful than men’s.” The woman also claimed that he referred to a client as a “porn star.”
Considered himself ‘politically incorrect’
The complaints of the three victims were found to be substantiated in an earlier hearing in April 2024. The NSW Civil and Administrative Tribunal concluded that Mr Waterstreet’s actions violated professional conduct standards. During the hearing, the tribunal heard how Mr Waterstreet had said on a podcast in 2023 that he was “politically incorrect.” He also said that past inappropriate incidents had merely been “slips of the tongue.”
The Tribunal also questioned him about his website, where he had written that he was “on sabbatical.” Mr Waterstreet defended the wording, saying that it “was a way of putting a very uncomfortable experience … without saying ‘I’ve been cancelled.'”
‘I am embarrassed and ashamed’: Barrister blames bipolar
Mr Waterstreet tried to explain to the Tribunal that his misconduct was partly due to his bipolar disorder. He said that he was diagnosed with the condition in 2022 and that this helped to shed light on why he acted the way he did.
“I am embarrassed and ashamed by the grossness and uncurbed nature of my conduct,” Mr Waterstreet stated. “I didn’t understand sexual harassment. I thought it was subjective and intention played a part.”
His one-year ban from practicing law was not the only punishment Mr Waterstreet faced. In 2018, he declared bankruptcy due to not being able to pay more than $420,000 in unpaid taxes. The debt had seen him slum it in a backpackers’ hostel, but he has since moved into an apartment. Mr Waterstreet was also ordered to pay the legal costs of the NSW Bar Association.

Solicitor ordered to pay $170K, barred from practicing for sexual harassment
In July 2024, the principal solicitor for a boutique law firm was refused a certificate to practice law by the NSW Law Society. This came after the solicitor, Owen Maldwyn Hughes, was ordered to pay $170,000 to his former employee, Catherine Hill, for sexual harassment.
Mr Hughes’ refusal of a practice certificate was reported by media, citing the Office of the NSW Legal Services Commissioner’s register of disciplinary action. The NSW Law Society had refused the certificate as Mr Hughes did not declare that he had a sexual harassment claim against him when he submitted his application.
“Walking on this knife’s edge’: Female paralegal bombarded with romantic emails
In 2015, Ms Hill started working for Mr Hughes at the firm Beesley and Hughes, based on the north coast of NSW. In 2019, the Federal Circuit Court found that Mr Hughes engaged in “relentless” inappropriate behaviour towards Ms Hill. This started shortly after she joined. Despite her clear rejection of his romantic advances, the Court said that Ms Hill was subjected to a “bombardment of emails” from Mr Hughes.
This was despite her making it “abundantly clear” that she had no romantic interest in him. The Court found that one of the emails included “veiled threats” linking her job security to her compliance with his desire for a romantic relationship.
“The vast majority contained romantic propositions,” Miss Hill told the ABC. “I was always walking on this knife’s edge of trying not to somehow upset him because I’d lose my job.”
Solicitor entered female colleague’s room in underwear
The misconduct escalated during a work trip to Sydney. Evidence provided to the Court stated that Mr Hughes considered this trip an “opportunity” to begin a “sexual relationship” with Ms Hill. It was alleged that he “tried his luck” in forging this relationship by entering Ms Hill’s hotel room wearing only his underwear.
Mr Hughes claimed that he was in his underwear because he was being “eaten alive” by mosquitos. Ms Hill told the ABC that when she asked him to leave her room, he “asked for a hug.” The Court said that this was a “dishonest attempt…to hide his true motivations.”

Tried again next morning
The Federal Circuit Court noted how Mr Hughes entered Ms Hill’s room again the next day under the pretext of retrieving some papers he had left there. However, the Court said that his intentions were “entirely sexual.” It said that he was “hop[ing] that he would see her naked (as she was clothed only in a towel) or to watch her get dressed.”
When the duo returned from the Sydney trip, Mr Hughes “coerced hugs” from Ms Hill. He did this by “blocking her exit and putting her in a position where she felt she could not decline.”
Solicitor blamed paralegal for being ‘flirty’
Ms Hill’s legal team accused Mr Hughes of “slut shaming” her for attempting to blame his behaviour on what he told the Court was her “flirty and coquettish” personality. He claimed that she wore “alluring dresses to the office.”
The Court, however, labelled this attempt to shift blame as “utterly outrageous.” It said that “it is the mark of a bygone era where women, by their mere presence, were responsible for the reprehensible behaviour of men.”
‘Particularly sinister’: Court slams solicitor for sexual harassment
The Federal Circuit Court noted that Ms Hill was forced into a terrible situation, particularly because she was divorced and had children. It said that it was “entirely reasonable” for her to stay in the role at the firm as she had “limited career opportunities.” The Court said that the “power imbalance” between Mr Hughes and Ms Hill was “mind boggling.”
It said that she had been “significantly and adversely impacted” by the sexual harassment she experienced from Mr Hughes. And it was noted that she was receiving mental health care as a result. The Court said that Mr Hughes’ conduct was “particularly sinister” due to the “intertwining” of her job with his desire to have a romantic liaison with her.

Paralegal wins huge sexual harassment payout
The Federal Circuit Court said that Ms Hughes’ misconduct was “a very grave example of sexual harassment.” It said that as a solicitor, he “not only should know the law but should conduct himself in a very high standard befitting of his position in society.”
The Court ordered Mr Hughes to pay Ms Hill $170,000 in damages. This included $120,000 in general damages and $50,000 in aggravated damages
Lawyer who said client could pay with oral sex ordered to pay $235K
This story, which made headlines in October 2024, comes to us from Canada. It involved a suspended lawyer, James Bowie, who was forced to pay C$235,000 (around A$268,000) for his “shocking” behaviour towards a client. The client, Leanne Aubin, was awarded the compensation by the Superior Court in the province of Ottawa.
Ms Aubin alleged that Mr Bowie had proposed his legal services in exchange for oral sex. She also claimed that he disclosed personal and confidential information about her allegations, which caught the attention of media.

Client sought lawyer after bar fight
According to court documents, Ms Aubin sought Mr Bowie’s legal assistance in 2022 after being charged with assault with a weapon. The assault took place in an Ottawa bar. Ms Aubin had been called a sexist slur by a man, which prompted her to throw a plastic beer pitcher at him.
The man responded by picking up Ms Aubin’s phone and throwing it at her face. He was not charged by police, despite having broken a bone in Ms Aubin’s face. However, the charges against her were later dropped when she engaged a different lawyer.
‘It’s hot for me:’ Lawyer proposed oral sex payment via Snap Chat
The Court heard how, when Ms Aubin had first sought his services, Mr Bowie had asked her to contact him via Snap Chat, where messages are automatically deleted. He said that he needed a $4,000 retainer, but Ms Aubin was worried about being able to afford his fees. A few weeks later, Mr Bowie proposed a sex-for-services arrangement for his legal representation.
Ms Aubin told him that she was not interested in such an arrangement. However, Mr Bowie kept proposing it to her. Ms Aubin’s lawyer presented to the Court Snap Chat messages in which Ms Aubin tried to rebuff her lawyer’s proposition.
“I told you before, I’d rather pay [for legal services with] cash than head, [which is] a reference to oral sex,” the lawyer said in court, reading a message Ms Aubin had sent to Mr Bowie.
“Not something I’ve ever done before. And as much as I’m desperate, I don’t want to do anything I’ll regret, at least until I know [my ex partner] isn’t coming back.”
Mr Bowie replied that “it’s hot for me.” To this, Ms Aubin said, “There’s nothing about trying to keep my life from crumbling that turns me on, lol.”
In addition to this proposal, Mr Bowie had sent his client a dick pick on the day of her criminal hearing.
Lawyer leaked confidential details on social media
Ms Aubin told the Superior Court that Mr Bowie had leaked details of the assault online. She said that it led to media attention that left her with “crippling emotional distress.” Ms Aubin said that she has since had “extremely difficult” mental health issues and experienced a “social, professional and financial fallout.”
The Court ruled that Mr Bowie’s public disclosure of Ms Aubin’s personal details on social media, after she filed her complaint, further compounded his breach of fiduciary duty.

Woman wins huge sexual harassment payout
Bowie was ordered to pay Ms Aubin $75,000 for breach of fiduciary duty, $65,000 in damages, $30,000 for defamation, and $25,000 in punitive damages. Additionally, he was directed to contribute $40,000 toward Ms Aubin’s legal costs.
“The lawyer-client relationship is founded on trust,” the Superior Court said. “That trust is why persons can and do confidently bring their most intimate problems and all manner of matters, great or small, to their lawyers.”
Read More: Sexual Harassment Cases
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