Stephen A's Take: An 84-year-old woman left her entire $1 million estate to a younger man

Summary

Detailed Summary of "The Stephen A. Smith Show" Episode: "Stephen A's Take: An 84-year-old woman left her entire $1 million estate to a younger man"

Release Date: June 26, 2025
Host: Stephen A. Smith
Platform: iHeartPodcasts

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Introduction

In this episode of "The Stephen A. Smith Show," hosted by Stephen A. Smith in collaboration with iHeartPodcasts, Smith delves into a controversial and emotionally charged legal case that has captured public attention. The episode primarily focuses on the unusual will of an 84-year-old woman from British Columbia, who left her entire $1 million estate to a significantly younger male escort. Throughout the discussion, Smith provides his unfiltered opinions, blending his characteristic candor with analytical insights into the societal and personal implications of such a decision.

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Case Overview

At the heart of the episode is the story of Janet Colville Sutherland Henry of North Vancouver. Jane Henry, after the passing of her husband in 2004, maintained companionship through various male escorts. In February 2021, a year before her death, she met Simon Garston, a professional companion and male escort in his late 20s, via Skype. Their professional relationship evolved quickly, leading to multiple overnight visits, with the last being a three-night stay. Subsequently, Henry revised her will, bequeathing her $1 million estate to Garston. This surprising decision became public knowledge only after her death, prompting family members to file a lawsuit contesting the will.

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Stephen A. Smith’s Analysis

Stephen A. Smith approaches the case with a blend of empathy, skepticism, and societal commentary. He begins by addressing potential criticisms that others might levy against Henry's decision, questioning her mental acuity or intent. However, Smith swiftly counters these notions by emphasizing Henry's long-term choice to engage male escorts, suggesting a level of control and awareness in her decisions.

Key Points Discussed:

1. Autonomy and Personal Choice:

   • Quote: "It's her money, it's perfectly within her right to leave it to whoever she chooses... he clearly feels fulfilled her to her lasting days." ([01:45])
   • Smith underscores the importance of respecting Henry's autonomy, highlighting that her decision reflects her personal fulfillment and satisfaction.

2. Societal Judgments and Stigma:

   • Quote: "Is that appropriate to say? I don't know... But it's true." ([03:10])
   • He acknowledges the societal discomfort and potential stigma surrounding Henry's choice but maintains that judgment should be reserved.

3. Family Dynamics and Relationships:

   • Quote: "Evidently, he did more for her than she felt her own family did for her." ([04:20])
   • Smith touches upon possible underlying family dynamics that might have influenced Henry’s decision, hinting at deeper relational issues.

4. Human Desires and Motivations:

   • Quote: "Everybody got that thing, clearly until her dying breath at age 84. That was her thing." ([06:10])
   • He reflects on the universal nature of personal desires and how they shape our life choices, irrespective of age.

5. Personal Anecdotes for Relatability:

   • Quote: "One of my uncles was like that... everybody has things that stimulate them in certain ways." ([05:30])
   • By sharing personal stories, Smith connects the case to broader human experiences, making the discussion relatable to listeners.

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Notable Quotes with Timestamps

• Autonomy in Decision-Making:

  • "Whatever proclivity she had that she could have fulfilled herself and needed to be fulfilled by somebody else, he handled." ([02:15])

• Respect for Personal Fulfillment:

  • "If it's her money, it's perfectly within her right to leave it to whoever she chooses." ([01:45])

• Acknowledging Societal Norms:

  • "Is that appropriate to say? I don't know. I don't know." ([03:10])

• Universal Human Desires:

  • "Everybody got that thing, clearly until her dying breath at age 84. That was her thing." ([06:10])

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Conclusion

Stephen A. Smith navigates the delicate subject of Janette Henry's final testament with a balanced perspective, advocating for personal autonomy while acknowledging the complex emotions and societal judgments that arise in such cases. By interweaving personal anecdotes and straightforward commentary, Smith not only informs but also invites listeners to reflect on the broader implications of personal choice, fulfillment, and the dynamics of familial relationships in the face of unconventional decisions.

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Note: The transcript provided primarily contained advertisements and a segment beginning at [01:19] where Stephen A. Smith discussed Janette Henry's will. The summary reflects the depth and breadth of that discussion based on the available transcript.

Transcript

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I had to react to this story Family members are suing after an 84 year old British Columbian woman left her 1 million estate to a male escort. Janet Colville Sutherland Henry of North Vancouver changed her will shortly before she died, leaving her estate to escort Simon Garston. Henry's husband died in 2004 and following that she paid various male escorts for companionship and sexual Services. In February 2021, a year before she died, Henry met Garston, who was in his late 20s and worked as a professional companion and male escort. The two met via Skype and the significant fees for his services were discussed and agreed to. They met in person for the first time in April of 2021 when Mr. Garstin came to the deceased home for an overnight visit, then met several times for overnight stays in the following weeks. Their last face to face meeting was for three nights. A few months before she died, Henry changed her will, leaving her approximately $1 million estate to Garstin. The family did not know about the change until after her passing. This is not going to be the most popular opinion, I'll confess, but are you challenging her mental acuity? Are you challenging her cogency? She seems to be an elderly woman who was who was in control of her faculties and was completely aware of what she was doing. How do we know this? Because she had several male escorts and then she met him and she want nobody else. Ladies and gentlemen, in English. That's a brother that was handling the business. Is that appropriate to say? I don't know. I don't know. But it's true. Whatever proclivity she had that she could have fulfilled herself and needed to be fulfilled by somebody else, he handled. And it might be sad, hell, it might be pathetic. But if it's her money, it's perfectly within her right to leave it to whoever she chooses. And if she chooses to leave it to a man who happens to be a male escort, that she clearly feels fulfilled her to her lasting days. You know what I'm saying? How can you not that? Evidently, he did more for her than she felt her own family did for her, which is why she left the $1 million estate to him. Now, I'm not saying it's right. You would like to think life, there's more things to life than getting you freak on. But evidently, to her, it really, really was. Mattered most. Was what mattered most. And she seems very, very appreciative of his efforts. And if that's the case, I'm not saying he's supposed to like it. I'm not saying it's not a little bit trifling, but you gotta live with it. Me, myself, you know how you in your 20s getting excited about that. But, you know, everybody has things that stimulate them in certain ways. One of my uncles was like that. You know me, I like a voluptuous figure. My boy Pulley, he wants you the size of Rasputia from Norbit, all right? One of my other boys, he wants you number, skin and bones. But my uncle, his aphrodisiac, what turned him almost was money. If you could make this brother money, he didn't give a damn whether you were white, black, Asian, Hispanic, fat, skinny, mid range, cellulite firm skinny. It didn't mean a damn thing to him. Green was what turned him on. It really, really turned him on. That was him money. I'm not talking about myself. I swear, I'm not talking about myself. I'm talking about him. But it's the truth. Everybody got that thing, clearly until her dying breath at age 84. That was her thing.

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[A]

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