The friend, the family, their aunt and her lover: Court fight looms over $1M estate left to male escort

The will of a deceased B.C. woman will be contested by an old friend, her closest living relatives and a male escort approximately 54 years her junior following a decision by a provincial Supreme Court judge.

Janet Henry died in North Vancouver in November 2021 at the age of 84 and left most of her estate, valued at around $1 million, to Simon Garstin in her August 2021 will.

Garstin is described by Justice Gary P. Weatherill as "a professional companion and male escort who, in exchange for money, provides companionship and sexual services to women." He is presently in his early 30s, the judgment said. 

Henry's bequest to Garstin is being challenged, however, by her two closest living relatives, Australians Jillian McCrone and Ross McCrone, her niece and nephew. They are seeking to have the estate distributed between them.

They allege their aunt did not have the capacity to understand the nature and impact of her August 2021 will and did not receive independent advice crafting it.

They also allege Garstin "unduly influenced" Henry in preparing the will and that he was in a "position of control and dominance" over her.

A second challenge to the will comes from a friend of Henry's, Douglas Wilson. He met Henry in 2009 as her trainer although they became friends over time.

Wilson moved to Australia in 2018 but they kept in touch via phone and Facebook. A February 2021 will from Henry would have made him the beneficiary of the estate. 

In both 2021 wills, the McCrone siblings are named as contingent residual beneficiaries, meaning they would inherit the bulk of her estate if either Wilson or Garstin — depending on the version — predeceased her.

In a decision issued late last week, Weatherill confirmed that the McCrones' and Wilson's challenges to the testament naming Garstin as beneficiary will proceed almost four years after Henry's passing.

Family claims aunt was 'very vulnerable'

Henry had no children. Her husband died in 2004 and her brother passed away a year before her.

"Following her husband's death, [Henry] apparently enjoyed retaining and paying for the services of various male escorts for the purpose of companionship and sexual services," Weatherill wrote.

The McCrones' statement of claim alleges that during the COVID-19 pandemic, Henry was "isolated and became very lonely and depressed."

"Due to her isolation, loneliness and depression she became very vulnerable," it says.

In January 2021, Henry retained Garstin, Weatherill wrote, as a companion. They spoke via Skype and "fees for Mr. Garstin's services were discussed and apparently agreed to."

Garstin, Weatherill wrote, spent a total of seven nights at Henry's North Vancouver home from April to October of that year.

Jillian McCrone's affidavit alleges the relationship consisted of more than those visits.

It included screenshots of WhatsApp messages between her aunt and Garstin — allegedly professionally known as Sam Gaines — that she asserts shows him becoming "more and more involved in my aunt's life."

The texts included in the affidavit covered a wide range of topics, including Henry's diet, health, financial matters and even the pair's differing views on the COVID-19 pandemic.

"Good morning Simon, you are going to be horrified but I am getting the vaccine. I'm hesitant but it has to be done," Henry wrote in one exchange.

"It's too bad you don't listen to anyone with common sense. I have tried to tell you in very plain detail but you don't seem to want to listen. So I think you are gambling with your life," Garstin replied.

"In a March 24th WhatsApp, Mr. Garstin ... berates and is dominant towards my aunt, in the end she states she 'trusts' Mr. Garstin," Jillian McCrone's affidavit reads.

"By 15th June my aunt is convinced and believes she and Mr. Garstin are in a relationship [and] she informs her GP that she has a partner who she has been seeing for a while."

Escort denies dominating 'sophisticated' woman

Garstin, in a response to the claim, denies Henry was "isolated, lonely, depressed or vulnerable."

She had been single and living independently for over 15 years, he said. She started and ran a successful business. She was "sophisticated, and lived in relative financial comfort."

"[Henry] paid [Garstin] for his time and companionship, and … his financial security, at times, was dependent on [Henry's] payment," it adds.

"If anything … the nature of their relationship put Janet in a position of dominance over him, and not the other way around."

Garstin denies discussing Henry's estate plan with her and denies requesting any part of her estate.

However, Garstin added, in their last meeting, Henry advised him that "'if she died, her accountant would contact him' or words to that effect," reads the response to the claim.

"This defendant now understands this was a reference to him being included in the will, but he did not understand or appreciate that at the time."

It goes on to say "this defendant says that the will is valid in all respects, and reflects Janet's fixed and final intentions with respect to her estate."

Wilson, the old friend, is a new entrant to the legal fray. 

Weatherill wrote that Wilson knew of Henry's death shortly after it happened but it wasn't until the McCrones' lawyer contacted him seeking information that he learned about the legal proceedings — and that he had been named beneficiary of the estate in the February 2021 will.

Weatherill noted in his ruling that a trial on the matter was set to begin June 30, but Wilson filed an application Monday to adjourn so his lawyer can review documents and discovery transcripts.