Heavyweight – Episode: "Deborah"

Podcast by Pushkin Industries | Host: Jonathan Goldstein | Date: December 18, 2025

Episode Overview

In this deeply moving episode of Heavyweight, host Jonathan Goldstein helps 102-year-old Deborah revisit a pivotal love and heartbreak from her youth, unearthed through a box of long-hidden letters from her first fiancé, Jerry Robbins, who died in World War II. What begins as a lighthearted phone call turns into an emotional journey of discovery, memory, grief, and catharsis, as Deborah and her family reckon with the return of a love lost for nearly eight decades.

Key Discussion Points & Insights

1. Introduction: The Box in the Snake Pit (03:34–07:32)

• Discovery: Deborah’s daughter, Lee, prompts her to clear out a heavily cluttered storage room (“the snake pit”) in her Bronx apartment, uncovering a box labeled “go through.”
• Contents: Inside are 256 letters from Jerry Robbins, Deborah’s first love and wartime fiancé, written when she was 21.
• Backstory: Deborah and Jerry were engaged before he was killed on Christmas Eve, 1944. Grief led her to seal away the letters, never reading them—until now.
  • Quote:
    “256 letters written to me when I was 21.” – Deborah (05:22)

2. Confronting the Past & “Jerryland” (07:32–12:31)

• Rediscovery: Deborah becomes fixated on Jerry’s words and memory, reading the letters daily and feeling herself “fall in love with Jerry again.”
  • Quote:
    “How can a 101-year-old woman, whose hormones have long since shriveled, fall in love again?” – Deborah (08:56)
• Family Concern: Daughters Lee and Lauren observe their mother becoming obsessed, living in “Jerryland,” sidelining other interests and even overshadowing memories of her late husband, Irving.
  • Quote:
    “All she did was live in Jerryland.” – Lee (09:30)
• Reflection on Aging: The family discusses how aging can distill our truest selves.
  • Quote:
    “They always say we become more of ourselves the older we get.” – Lee (11:40)

3. The Mandate: Giving Jerry a Voice (13:05–15:23)

• Purpose Emerges: Deborah expresses a new, urgent life mandate—bringing Jerry’s writings to the world. Jonathan and Lee agree that sharing the letters might help her “leave Jerryland” and find closure.
  • Quote:
    “Now that I’ve lived this long, my mandate is to do something with these amazing letters.” – Deborah (13:26)
• Plan: Jonathan will visit Deborah in New York to help sort through the letters and publicly share Jerry’s story.

4. Journey Into the Letters: Passion, War, and Youth (19:23–28:02)

• Letter Reading: Jonathan, producer Phoebe, and Deborah review all 256 letters. Excerpts reveal Jerry’s poetic language, wit, and the deepening romance between the two.
  • Quote:
    “Instead of war, he says, ‘man made madness;’ instead of bullet, ‘hot sperm of death.’” – Lauren describing Jerry’s writing (22:42)
• Love Unfulfilled: Deborah regrets not consummating the relationship, having waited for marriage.
  • Quote:
    “It was never consummated, which is my regret.” – Deborah (20:47)
• Separation and Ritual: During Jerry’s military service, the couple maintains a ritual of being “together” every night in thought—a moment called “now.”
  • Quote:
    “The only thing that was real was here and now.” – Deborah (25:37)

5. Loss, Grief, and the Aftermath (28:10–32:55)

• Tragedy Unfolds: Jerry is killed when his troop ship is torpedoed crossing the English Channel. For decades, details of the tragedy—the sinking of the Leopoldville—are covered up by the government.
• Deborah’s Grief: The abrupt end of the letters reverberates; Deborah reveals the re-emergence of grief, feeling “less happy” and haunted by nightmares of Jerry’s death.
  • Quote:
    “In a certain way, the discovery of those letters have turned my life upside down. Because I don’t feel as happy as I used to feel.” – Deborah (30:53)
• A Path Forward: A genealogist discovers that Jerry’s body was actually repatriated to a nearby New York cemetery—information Deborah never knew.

6. Pilgrimage to Jerry’s Grave: Memorial and Catharsis (33:03–45:35)

• Group Visit: With producer, family, and son-in-law/documentarian Joe Berlinger (who plans to film for his project), Jonathan accompanies Deborah to Mount Lebanon Cemetery.
• The Moment at the Grave: Deborah had prepared a speech, but giving in to the moment, she instead speaks passionately and spontaneously, lamenting the “madness of war” and honoring the lost young lives.
  • Memorable Moment:
    “No more. No more wars. Please, please, no more wars. There are too many beautiful, healthy young veterans who are lined up here and probably never had a chance to live. What thieves warmongers are. Warmongers are thieves of life that was never lived. Man made madness. Man made madness.” – Deborah at the graveside (43:41)
• Aftermath: Deborah feels unexpectedly energized, not in pain. The visit becomes a turning point, a reclaiming of strength and peace.
  • Quote:
    “I thought it would be painful, and it wasn’t painful. I got a refill of energy... that really came from being with Jerry.” – Deborah (45:44)

7. Closure and Moving Forward (46:13–47:08)

• Reflection: Jonathan observes that life’s unresolved stories do not simply fade; sometimes, if you live long enough, they resurface, demanding resolution.
• Life Goes On: The episode ends with the family celebrating a granddaughter’s birthday—life’s small moments after a major reckoning.
  • Quote:
    “All the little things that make up a life—all the little things that make up the here and now.” – Jonathan Goldstein (46:52)

Notable Quotes & Memorable Moments

• On love and regret:
  “As passionate as it was, it was never consummated, which is my regret.” – Deborah (20:47)

• On aging:
  “They always say we become more of ourselves the older we get.” – Lee (11:40)

• On rediscovered love:
  “I fell in love with Jerry again.” – Deborah (08:02)

• On the legacy of war:
  “Warmongers are thieves of life that was never lived. Man made madness.” – Deborah (43:41)

• On closure:
  “I thought it would be painful, and it wasn’t. I got a refill of energy... that really came from being with Jerry.” – Deborah (45:44)

Timestamps for Key Segments

• The Snake Pit & Discovery: 03:34–07:32
• Jerryland Obsession: 08:02–12:31
• Deborah’s Mandate: 13:05–15:23
• Reading the Letters & Romance: 19:23–28:02
• Jerry’s Death & Aftermath: 28:10–32:55
• Planning & Visit to the Grave: 36:43–45:35
• Back in the Van & Life’s Continuation: 45:44–47:08

Overall Tone & Themes

• Reflective, tender, and often gently humorous, with Jonathan’s trademark self-deprecating asides and rapport with guests.
• Examines the complexities of love across a lifetime, grief, the endurance of memory, and how unresolved stories seek their own conclusion.
• Closure does not erase the past but invites reconciliation with it, as life continues in a series of small, meaningful moments.

For More Information:

• Deborah is publishing a collection of Jerry’s writing (waitformeworld.com)
• Lee is hosting a live read of her screenplay about Deborah and Jerry (January 20th, Jazz Forum, Tarrytown, NY)