A female assistant to Jeremy Diamond complained to police that the personal injury lawyer would not assign her potential clients to vet unless she wore provocative clothing, sent naked photos or had “sexual activity” with him, according to a Toronto police case synopsis provided to a Crown attorney in 2011.

“She only gets paid if Mr. Diamond gives her a client,” detectives wrote in the case synopsis.

Police, initially acting on a complaint by Diamond, had charged the female assistant with extortion. She had threatened to expose the activities of the very public face of the Diamond & Diamond law firm.

After further investigation into the case, the detectives changed their minds. They asked a senior Crown attorney to withdraw the charge against the assistant, concluding instead that there was “sufficient evidence to charge (Diamond) with extortion.”

When the matter came to court, Crown attorney Michael Callaghan withdrew the charge against the assistant, saying Diamond’s conduct made him conclude it was not in the public interest to pursue the case against the assistant.

“There may be a reasonable prospect of conviction (of the assistant), but given the conduct of the complainant (Diamond) in the matter, I have real concerns that it was not in the public’s interest to proceed, and as such that’s why I’m withdrawing this charge today,” Callaghan told a justice of the peace hearing the case in August 2011.

Diamond was not charged with extortion.

Asked about the allegations against Diamond in the police synopsis, Diamond’s lawyer, Julian Porter, told the Star his client “denies them with a passion.” Porter said they are from a “disgruntled former contractor” and he is appalled the paper would publish what he termed “anonymized allegations of serious criminal conduct” that did not result in charges or prosecution against his client.

“The unfairness of this is monstrous,” Porter wrote in a letter to the Star.

A recent Toronto Star investigation revealed that Diamond, who has been described as an “award-winning personal injury lawyer,” has never tried a case himself. The Star found his firm, Diamond & Diamond, has for many years been attracting thousands of would-be clients through a U.S.-style advertising campaign and then referring cases to other lawyers in return for sometimes hefty referral fees.

Porter told the Star that Diamond & Diamond has hired lawyers to handle cases in-house and currently has “thousands” of clients on retainer. Porter said the firm does refer out “some individuals,” but would not say how many.

Prior to 2013, Diamond & Diamond was mainly a referral firm. During this time period, when prospective clients called, assistants were assigned to meet with them and assess the complexity of the case before it was referred out to a lawyer at another firm.

One assistant who did this work was the woman who would become caught up in the extortion case. According to the police synopsis, she had worked for Diamond and the law firm for two years.

In May 2011, the woman wrote to Diamond complaining of harassing behaviour and demanding $60,000, or she would contact the Law Society of Upper Canada, Diamond’s wife and the Toronto Sun newspaper.

“I’ve had enough of everything you have done to me in the last 2 years … sexual harassment (many different examples) and not giving me respect as an employee,” the assistant wrote in her letter to Diamond.

“I have told you several times that you are inappropriate and that I demand respect. You have severe issues and these are the consequences.”

The woman said she could ruin Diamond’s reputation with “one phone call,” telling people he cheats on his wife, speaks inappropriately about his clients and other employees, has a “party house,” and has relationships with “paid to party girls.” She gave him a May 6 deadline to pay the money.

“I have pictures, emails and conversations saved that show all this,” her message said. “I will notify the Law Society of what you are doing.”

Diamond’s response was to call a Toronto lawyer, and the two showed up at an east-end Toronto police station the day before the deadline, telling detectives he was a victim of extortion.

Diamond provided detectives with the May 2 letter sent to him by the assistant, and a series of texts on his phone that he had sent to her after receiving her letter.

JD: Excuse me???

JD: Are u trying to extort me??

JD: why would u try and do such an absurd thing?

JD: I understand you need money but why start making up lies like this? Please call me to discuss this. tx

JD: I was very respectful towards you and was extremely accommodating.

JD: I understand you’re going through issues but to try and extort me is not the proper way to go about things.

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Diamond also told police the former employee had “valuable and sensitive documents relating to his law practice that in the wrong hands could be detrimental to his confidentiality agreements with his clients,” according to the police synopsis provided to the Crown attorney.

Early the next morning, detectives arrested the assistant at her home and charged her with extorting Diamond. On the drive back to the police division, the assistant said there was another side to the story. She gave a videotaped statement to police and later provided other information as police expanded their original investigation.

Among the information she turned over were text messages, emails and pictures.

The former employee told police she wrote the letter to Diamond “in frustration” because of what she indicated was sexual harassment she had experienced, according to the police synopsis.

“She has produced emails indicating that in order to get clients she would have to wear provocative clothes, provide Mr. Diamond with naked pictures or have sexual activity” with him, the document says.

The former employee told police she had spoken to two human rights lawyers who told her she could expect to get between $60,000 and $80,000 if she sued Diamond.

In the text messages provided to police, it appears that Diamond made lewd remarks as the employee rebuffed his attempts to flirt. In one exchange, Diamond commented on modelling pictures of the former employee posted to her Facebook page.

“f--k I exploded so hard looking at them,” he texted.

When the employee texted back “xx ummm … that’s inappropriate Jeremy,” he responded by texting: “why ur so hot babe, I think about f---ing you all the time … I want to bend you over my desk and stick my throbbing c--k inside you … you would love it babe.”

The employee responded: “enuff seriously.”

Diamond texted: “lol you are no fun.”

In another text exchange, the former employee attempted to discuss a meeting for work, indicating a wish to send out invoices.

Diamond replied: “okay wear some sexy lace lingerie.”

Through Porter, Diamond denied the authenticity and accuracy of the text messages. He said his client was never interviewed by the police “in relation to the potential charges against him described in your letter.”

Porter did reference the letter the assistant sent Diamond, which in turn is referenced in the police synopsis to the Crown.

“The extortion letter Mr. Diamond received is a classic example of unequivocal extortion. It is smeared with evil,” Porter wrote to the Star.

The Star is not naming the woman due to the nature of the allegations and was unable to get comment from her.

Police sources said that in consultation between the police and the Crown it was “suggested that the threshold to get a conviction against a lawyer is very high” and it was therefore not in the public interest to pursue the case against Diamond.