Proxy x Heavyweight

Proxy x Heavyweight: The Story of Anita and Stefano

Podcast: Proxy with Yowei Shaw
Episode: Proxy x Heavyweight (Heavyweight’s “Stefano”)
Date: November 18, 2025
Host: Jonathan Goldstein (Heavyweight), with Proxy introduction by Yowei Shaw
Case Subject: The search for Stefano, the baby Anita comforted and transported from Italy to the US for adoption in 1959

Episode Overview

This episode is a cross-post from the podcast Heavyweight, featuring host Jonathan Goldstein’s signature approach: helping guests revisit a defining, unresolved moment in their lives. The story centers on Anita, an Italian refugee who, as a young woman, escorted a two-year-old orphan, Stefano, to America for adoption in 1959, bonding deeply with him during the flight. For the rest of her life, Anita wondered what became of Stefano—a mystery her daughter Debbie is determined to solve after Anita’s death.

Main themes:

Enduring, unrequited love and the bonds of care
The impossibility and longing of closure
Adoption, displacement, and immigrant experience
Hope, disappointment, and the limits of investigative empathy

Key Discussion Points & Insights

1. Introduction & Context (00:00–04:12)

Yowei Shaw (Proxy) sets the stage, praising Heavyweight's focus on “messy, hard to talk about emotional conundrums.”
Jonathan Goldstein introduces Anita’s story: an Italian emigrant escaping postwar Yugoslavia, eventually escorting Stefano for adoption, and the lifelong impact this one-day relationship had on her.

Notable Quote:

“The stories are funny, heartbreaking, healing, and often make you laugh and cry in the same breath, which is my favorite kind of podcast.”
— Yowei Shaw (00:46)

2. Anita’s History & Character (04:12–09:36)

Debbie (Anita’s daughter) shares anecdotes about her mother’s “fierce optimism,” even amidst hardship as a refugee.
Anita’s defining story: the bond with Stefano during their 18-hour journey from Rome to New York—both venturing alone into a new world.

Timestamps & Quotes:

[04:12] Debbie: “For her, the glass was beyond half full. It was always full, even if there was a drop of water in there…”
[07:14] Anita (in old video): “It’s so cute. Look at how beautiful he is, Stefano.”
[08:53] Anita: “He was like my baby.”
[09:23] Anita: “I would like to know him and see how he’s doing. ... I was thinking all this year about him all the time. … And I love you, even if I don’t see you too long.”

3. The Search for Stefano (09:43–15:43)

After Anita’s death, Debbie and her friend Lindsay intensify their search.
Lindsay tracks down Stefano’s likely new identity (Stephen), but finds troubling hints of a criminal record and estrangement from family.
They hesitate, fearing for Anita’s safety if Stefano might be dangerous.

Quotes:

[10:39] Lindsay: “I have a skill for finding digital footprints of people. … I’m the person that people go to if they want to know something.”
[12:12] Lindsay: “We just...weren’t sure if maybe this was our safest way to go about this.”

4. Renewed Grief and Motivation (12:57–14:09)

Anita’s death coincided with COVID-19 and Debbie’s father’s dementia. Debbie never found closure.
Lindsay believes finding Stefano is essential for Debbie’s healing.
Debbie wants Stefano to know “that this woman thought of him for most of his life, loving him from a distance, wondering about him, praying for him.”

5. Heavyweight Investigation: The Search Intensifies (14:36–19:37)

Jonathan and producer Kahlilah Holt cross-check public records, discover Stefano’s “criminal record” is just an old DUI.
A string of dead phone numbers and unanswered messages. Letters are mailed, “three hopeful birds.”

Notable Quote:

[15:36] “So there’s really no other criminal past except...That’s all I’m seeing.” — Debbie, when learning Stefano’s criminal record is only a dated DUI.

6. Breakthrough and Reconnecting (18:42–21:12)

Two years after initial attempts, Stephen (Stefano) finally responds.
Stephen is surprised, wary of scams, and admits living off-the-grid with no computer or smartphone.
He agrees to a phone call with Debbie.

Notable Quotes:

[21:06] Debbie: “You were always on her mind for many, many years and told many people about you.”
[21:12] Stephen: “Well, God bless your mom. I wish she would have adopted me.”

7. Stephen’s Story: A Nominal Life (21:29–28:19)

Stephen describes being told about his adoption at age 8.
Adoptive family was not abusive but not especially close or loving—“three squares a day,” occasional “lickens” for discipline.
Stephen struggles with alcoholism, chronic isolation, and estrangement from his brothers.
He’s never married, lived with a partner (Joanne) for many years until her death from cancer.

Notable Quotes:

[22:46] Stephen: “Well, I have a serious alcohol problem. ... I was pretty much known as a boozer back in the day.”
[24:39] Stephen: “Joanne? She died of lung cancer, and I lived with her for, like, nine years.”

8. Emotional Disconnection & Missed Gifts (26:00–29:03)

Debbie offers to play Anita’s recorded message for Stephen, but he declines. He’s indifferent, even dismissive.
For Stephen, the connection is tenuous: “That could be anything. Like, I love this little toddler, you know, I love pizza. It could be anything.”
He cuts the call short but does request the photograph of himself with Anita as a baby.

Quotes:

[27:13] Stephen: “That could be anything. Like, I love this little toddler, you know. I love pizza. It could be anything.”
[28:22] Jonathan: “Do you feel like it’s too late?”
Stephen: “Yeah, I do.”

9. Aftermath and Reflection (29:26–31:43)

Debbie is heartbroken that Stephen didn’t want to hear Anita’s voice: “I think the part that makes me cry a little bit is that he didn’t want to hear my mom.”
Jonathan reflects on the nature of longing and gift-giving: “You can never assume a gift, you know?”
Debbie wonders if Anita might have been better not discovering the reality of Stephen’s life.
Jonathan draws a poignant observation: love often fails to land, but the act of trying is a form of hope.

Notable Quotes:

[30:47] Debbie: “The details he shared contained a lot of sorrow.”
[31:06] Debbie: “She would have told him she loved him. She probably would have invited him over, really. She would have figured out a way to feed him. My mom loved deeply.”
[31:43] Jonathan: “We live our lives in the desperate hope that if we find the right words, tell the story the right way, our love will be understood.”

10. Final Notes & Poetic Closure (33:53–End)

The episode ends with a poetic narration reflecting on attempts, connection, and the spaces between us.
The lasting hope: perhaps Stephen will one day feel Anita’s care, through the photograph he requested.

Memorable Moments & Quotes (with Timestamps)

[09:23] Anita: “I would like to know him and see how he’s doing... I love you, even if I don’t see you too long.”
[21:12] Stephen: “God bless your mom. I wish she would have adopted me.”
[22:46] Stephen: “I have a serious alcohol problem. ... I was pretty much known as a boozer back in the day.”
[27:13] Stephen: “That could be anything. Like, I love this little toddler, you know, I love pizza. It could be anything.”
[28:22] Jonathan: "Do you feel like it’s too late?" Stephen: "Yeah, I do."
[31:06] Debbie: “[Anita] probably would have invited him over, really. She would have figured out a way to feed him.”
[31:43] Jonathan: “We live our lives in the desperate hope that if we find the right words, tell the story the right way, our love will be understood.”

Timestamps for Key Segments

00:00–04:12 — Introduction and framing from Proxy and Heavyweight
04:12–09:36 — Anita’s history, optimism, and the origin of the Stefano mystery
09:43–12:24 — The hunt for Stefano: early attempts and dead-ends
14:36–15:43 — Digging up records, the criminal flag, and hesitation
18:42–19:16 — Contact! Stephen responds after years of silence
20:17–29:03 — The call with Stephen: unraveling the reality, barriers, and his indifferent response
29:26–31:43 — Debbie and Jonathan process the outcome and contemplate meaning
33:53–End — Poetic and musical coda

Tone & Style

The episode is tinged with the characteristic bittersweetness of Heavyweight: empathetic, wry, quietly funny, and profoundly humane. There are moments of both raw emotion and ironic detachment. The investigation is not tidy; real life remains unresolved, messy, and sometimes disappointing—but always deeply felt.

Conclusion

The search for Stefano is emblematic of our yearnings—for closure, for love to be felt across years and identities. Sometimes, as Jonathan observes, we need to accept that to love is to try, and not every gift will land. Yet, the act of trying, of reaching out, is still worthwhile—for Debbie, for Anita, and perhaps someday, even for Stephen.