Court Battle Brews Over B.C. Woman’s $1M Estate Left to Male Escort 54 Years Her Junior

A legal showdown is underway over the $1 million estate of a North Vancouver woman who left nearly everything to a man described as a professional companion and male escort more than five decades her junior.

Janet Henry, who died at 84 in 2021, named Simon Garstin — now in his early 30s — as the primary beneficiary in her final will, dated just months before her death. Garstin, who met Henry through his escort services, is now at the center of a court battle with her family and an old friend, both challenging the validity of that document.

The B.C. Supreme Court has ruled that the case will proceed to trial.

Will Wars: Friend vs. Escort vs. Family

Two versions of Henry’s will from 2021 are at the heart of the dispute. An earlier version named her friend Douglas Wilson as beneficiary. The later version left the estate to Garstin. In both cases, Henry’s niece and nephew from Australia, Jillian and Ross McCrone, were listed as backup beneficiaries.

The McCrones argue Henry was vulnerable and isolated during the pandemic and unduly influenced by Garstin, who had allegedly become deeply embedded in her personal life.

Court documents include WhatsApp messages showing the pair discussing everything from health and finances to vaccines and personal feelings — with Garstin at times described as “berating” or “dominating” in tone.

“By June 15th [2021], my aunt believed she and Mr. Garstin were in a relationship,” Jillian McCrone said in an affidavit.

Escort Pushes Back: ‘She Was in Control’

Garstin has denied all allegations of manipulation. He claims Henry was independent, financially stable, and experienced in hiring escorts for companionship.

He insists their relationship was consensual and transactional — and that she had more control over him than the other way around.

“If anything, Janet was in a position of dominance,” Garstin said in his legal filing.
“She never discussed her will with me, and I never asked to be included in it.”

He admits that Henry once told him her accountant might reach out if anything happened to her — a statement he says he now realizes referred to the will, though he was unaware of it at the time.

Garstin maintains that the final will is “valid in all respects” and reflects Henry’s true wishes.

A New Player Enters: The Old Friend

Douglas Wilson, a former fitness trainer turned friend, had kept in touch with Henry after moving to Australia. He was unaware she had updated her will until the McCrones’ lawyer contacted him. Wilson was listed as the main beneficiary in her February 2021 will — just months before she revised it in Garstin’s favour.

Now, Wilson is seeking to delay the trial, originally set for June 30, so his legal team can review evidence.

Family: ‘She Was Lonely and Depressed’

The McCrones claim Henry became increasingly isolated and depressed during the pandemic and was susceptible to manipulation. They argue Garstin's influence over her went beyond companionship — into matters of health, diet, finances, and emotional dependence.

Justice Gary P. Weatherill, in allowing the case to proceed, described it as “unusual” and emphasized the importance of allowing all parties to present their arguments at trial.

What’s Next?

With trial proceedings now formally set, the court will have to determine whether the will reflects Henry’s independent intent, or whether her final wishes were improperly influenced by someone in a “position of control.”

If the will is deemed invalid, the estate could revert to Wilson or the McCrones — setting the stage for one of B.C.’s more unconventional inheritance battles in recent memory.