Deep Cover Presents: Snowball

“Shame, Scams, and The Stories We Tell Ourselves” — Special Conversation with Ollie Wards

Released December 22, 2025 | Hosted by Jake Halpern with special guest Ollie Wards

Episode Overview

In this special episode concluding Deep Cover Presents: Snowball, host Jake Halpern interviews Ollie Wards, creator and central figure of the Snowball series. Together, they reflect on the making of Snowball—a deeply personal investigation into Ollie’s family’s experience with a charismatic con artist (Leslie)—and discuss themes of family, vulnerability, shame, justice, and storytelling. Through a candid behind-the-scenes conversation, the episode explores what it takes to report on your own family, the psychology of scams, and how stories of deception are ultimately stories about the people we love.

Key Discussion Points & Insights

1. How Snowball Came to Be

• Personal Genesis: Ollie started recording while home in New Zealand for his father’s heart surgery, simply to document his dad’s philosophies and life stories. This quickly led to the family’s brush with Leslie—the “ancient history” everyone had mostly moved past (06:52).
  • Quote/Ollie (03:16):
    “This is the first time that I have been in a studio for this whole project. The whole thing was recorded in hotel rooms, in my apartment in New York under...doonas. Like duvet. The bedspread.”
• Initial Reluctance & Family Dynamics: Recording his own family was both an asset and a challenge. The informality and intimacy of audio reporting helped, but Ollie was acutely aware of balancing the roles of brother/son and journalist.
  • Quote/Ollie (14:41):
    “There was definitely times where it was a bit sticky...it starts with Greg and it ends with Greg, but it’s actually about all of us. And... moreover, it's about Leslie.”

2. Navigating Family Sensitivities

• High Wire Act: Interviewing his own family felt much riskier than normal reporting, with higher stakes for trust, privacy, and emotional fallout (05:05).
  • Quote/Jake (05:05):
    “When the sources are your own family members, it just seems like the stakes are exceptionally high.”
• Shame and Victimhood: One unique challenge was asking family members to relive and share their vulnerability and shame—particularly as scam victims.
  • Quote/Ollie (19:13):
    “The literature...about con artists says that they get away with it in so many cases because the victims feel ashamed...and the con sort of preys on that level of shame.”
  • Ollie also notes his own mother’s moment of solace, knowing they weren’t alone in being fooled.

3. The Story’s Emotional Core: Family over Fraud

• Realness Over Revenge: Rather than anger, what shines through is resilience, warmth, and ultimately a stronger family bond. The Wards confronted practical realities (“where are we going to live?”), ultimately choosing honest reflection over bitterness.
  • Quote/Ollie (34:44):
    “Family triumphs, and family always will. If there’s a strong family, is there anything more powerful in the world?”
  • Quote/Ollie (28:02):
    “It helped me understand...something so profound that impacted us all in different ways. And it is our family’s story.”

4. The Art (& Ethics) of Personal Storytelling

• Storyteller vs. Subject: Ollie discusses toggling between being a brother and being a reporter—for instance, when his instinct said to “turn the tape on,” but loyalty said to comfort his brother (26:56).
  • Quote/Ollie (26:56):
    “Being a family member and trying to walk that line between pressing for information...versus also knowing I’m sitting down with you for Christmas lunch later this year.”
• Universality of Family Stories: Many listeners reached out with similar tales: “Every family has a story” (05:33).

5. Tracking Down Leslie: Reporting Challenges & Confrontation

• Uncertainty and Persistence: Ollie doubted he’d ever find Leslie, but was driven by stubbornness and clues—tenaciously building connections across continents (17:05).
  • Quote/Ollie (17:05):
    “Not very confident. But I am a pretty stubborn person...She’s a real person. She’s out there. People leave trails.”
• The Pivotal Confrontation: The eventual meeting with Leslie (“in the car park”) was fraught—Ollie had seconds to connect, facing a masterful manipulator with quick recall and practiced evasions (40:53–43:33).
  • Quote/Jake (42:37):
    “You were patient with her...it’s kind of amazing she didn’t just drive away...you didn’t start off by just, like, confronting her with her lies.”
  • Quote/Ollie (43:33):
    “By the end of it, I’m reeling off her criminal record...we workshopped it at the beginning about being palms open.”

6. Justice, Resolution, and Empathy

• The “Lack” of Justice and Its Aftermath: Many listeners wanted more poetic justice; Ollie acknowledges the complex emotional aftermath, where the “villain” is left lonely and broken, while victims move on and strengthen.
  • Quote/Jake (34:01):
    “I left...weirdly satisfied...it's not that she got what she deserved, but, like, whatever feelings I might have had for wanting vengeance...were not there because I kind of felt like, look where she is.”
• Cycle of Fraud and the Psychology of Cons: Most con artists, Ollie notes, do not profit hugely—their heists are “flash in the pan” lifestyles that quickly collapse.
  • Quote/Ollie (44:53):
    “They’re not in it for the money...they very rarely get away with lots of cash...there is definitely a debt going on where she has to kind of pay the previous person a little bit to keep them off her back while she looks for the next stash.”

7. The Story Continues—Or Does It?

• Ongoing Impact & Closure: Ollie is now the point-of-contact for new victims, though he’s clear he can’t be the world’s Leslie-fixer (48:40). He reflects on whether Leslie herself could ever truly provide closure, given her nature.
  • Quote/Ollie (53:42):
    “If it was the right circumstances...maybe she would own up to some of it...I think we should all be open to that.”
  • Final Note/Ollie (51:00):
    “My family picked up the pieces and came closer together and moved on. And we all look back on it as just this strange, funny, insightful moment in our lives.”

Notable Quotes & Memorable Moments with Timestamps

| Timestamp | Quote | Speaker | |-----------|-------|---------| | 03:16 | “This is the first time that I have been in a studio for this whole project. The whole thing was recorded in hotel rooms, in my apartment in New York under...doonas. Like duvet. The bedspread.” | Ollie | | 05:05 | “When the sources are your own family members...the stakes are exceptionally high.” | Jake | | 14:41 | “There was definitely times where it was a bit sticky...it starts with Greg and it ends with Greg, but it’s actually about all of us.” | Ollie | | 19:13 | “Con artists get away with it because victims feel ashamed...and the con sort of preys on that level of shame.” | Ollie | | 26:56 | “Being a family member and trying to walk that line... pressing for information...versus also knowing I’m sitting down with you for Christmas lunch later this year.” | Ollie | | 28:02 | “It helped me understand ...something so profound that impacted us all in different ways. And it is our family’s story.” | Ollie | | 34:44 | “Family triumphs, and family always will. If there’s a strong family, is there anything more powerful in the world?” | Ollie | | 40:53 | “The confrontation starts to come on and...I'm like oh man, it's on.” | Jake | | 43:33 | “By the end of it, I’m reeling off her criminal record...” | Ollie | | 44:53 | “They’re not in it for the money...that pyramid gets bigger and bigger and bigger.” | Ollie | | 51:00 | “My family picked up the pieces and came closer together and moved on. And we all look back on it as just this strange, funny, insightful moment in our lives.” | Ollie | | 53:42 | “If it was the right circumstances...maybe she would own up to some of it...I think we should all be open to that.” | Ollie |

Timeline of Important Segments

• 03:16–05:05 — Ollie on family, podcast intimacy, first time in a studio
• 06:52–07:51 — How the story originated from a family interview
• 10:29–14:41 — Ethical/media challenges of reporting on one’s own relatives, particularly his brother Greg
• 17:05–18:07 — Tracing Leslie, the challenges and persistence required
• 19:13–22:07 — Shame, victimhood, and why cons work; family and psychologist Maria Konnikova’s insights
• 26:56–29:01 — Navigating family relationships during the investigation, positive changes
• 40:53–43:33 — The climactic confrontation with Leslie; tactical decisions and reflections
• 44:53–47:19 — Where did the money go? Psychology of fraudsters
• 48:40–50:17 — Ongoing impact; Ollie as touchstone for new victims, justice system limitations
• 51:00–53:49 — Reflections on story closure, possibility of more revelations, and what true resolution might look like

Final Thoughts

This special episode pulls back the curtain on the making of one of the most personal true crime investigations of the year. Ollie Wards and Jake Halpern explore the thin line between reporter and subject, the push and pull between justice and empathy, and the resilience of the family at the heart of the Snowball story. Listeners come away with a sense of hope—the assurance that, even in the wake of deception and loss, connection and truth-telling can bind a family more tightly together.

For further info on “Snowball,” listen to the full series or visit Pushkin.fm.