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

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.

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.

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.

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])

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.

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.