True Crime Obsessed — Episode 456: "Ruby Red Handed"

Release Date: September 23, 2025

Podcast Hosts: Jillian Pensavalle & Patrick Hinds
Documentary Discussed: Ruby Red Handed: Stealing America's Most Famous Pair of Shoes (Hulu)

Episode Overview

In this lively and sass-filled episode, Jillian and Patrick recap the Hulu documentary “Ruby Red Handed,” which chronicles the 2005 theft—and 2024 recovery—of the legendary ruby slippers worn by Judy Garland in The Wizard of Oz. With trademark humor and pop culture flourishes, the hosts dig into the true crime, queer culture, museum mismanagement, the cultural significance of the slippers, and their jaw-dropping $28 million auction sale. The episode is rich with nostalgia, side tangents, and a consistent lament over the lack of openly gay voices in the documentary.

Key Discussion Points & Insights

1. The Ruby Slippers as "America's Most Famous Shoes"

• Jillian and Patrick set the tone (01:42):
  The ruby slippers "are definitely the most famous shoes in the world" ([01:49]). The hosts marvel at their icon status—“Say you have the ruby slippers and everybody you meet is going to want to see the damn shoes.”
  • Quote: "I would classify them as the Holy Grail. That is the Rolls Royce. $18 million historic piece, part of our American culture." (Patrick, [01:57])

2. The Hulu Documentary — Initial Takes & Critique

• The hosts generally enjoy the documentary, praise its pacing and information, but lament the severe lack of queer voices, especially given The Wizard of Oz’s status as a gay-icon artifact.
  • Quote: “I was texting this morning and I’m like, the fatal flaw of this documentary, there’s not enough gays. There’s like no self-identified homosexuals in this.” (Patrick, [02:42])
  • Jillian: “We desperately need Jinkx Monsoon doing her Judy Garland from Snatch Game” ([02:46])

3. Grand Rapids & Judy Garland Festival

• Setting: The theft occurred in Grand Rapids, Minnesota (not Michigan) ([07:46]), hometown of Judy Garland. The town has turned Garland’s birthplace into a shrine, complete with a yearly festival and museum.
• The museum houses massive Wizard of Oz memorabilia; hosts riff on the collection’s cultural gravity and sometimes-kitschy charm ([08:42] – [09:16]).

4. Judy Garland’s Complicated Childhood

• The documentary paints an idyllic, sanitized account; Jillian delivers a corrective:
  • Quote: "Her mother was violently abusive, shoved Judy Garland into show business, was the first person to give her drugs… Like, that’s not the story we’re telling here. They want to tell the super cute one, but like, her mother was abusive in so many ways.” (Jillian, [12:34])
• The hosts wish for more nuance, as well as representation of queer cultural perspectives.

5. The Slippers: History & Cultural Impact

• The wizardry classic is discussed as fundamental to film and queer culture; the hosts geek out over trivia (the transition from sepia to color, different silent and animated adaptations) ([15:21] – [18:23]).
• Quote: "The impact of that imagery of going black and white into color has been used millions of times since then." (Jillian, [16:31])

6. The 2005 Theft: What Went Wrong?

Museum Security Failures:

• The shoes were loaned by collector Michael Shaw for the festival, placed in a display case with an unlocked plexiglass cover, and the alarm was disabled due to unruly children and “parental indifference” ([33:09]).
  • Quote: “They thought the best idea was to turn off the alarm. So not a parent in sight. And the museum thought the best idea was to disable the alarm instead of telling the kids and parents that what they’re doing is not allowed.” (Jillian, [33:24])
• Patrick and Jillian detail the fiasco: no nightly safe, no contract, no security, and incredulity that no one took basic precautions—even with a million-dollar artifact ([31:25], [32:29], [35:13]).

Insurance Shenanigans:

• Shaw had a $1M insurance policy and accepted an $800k payout. He surprisingly didn’t sue the museum, but the insurance company sued due to negligence ([37:42]–[39:02]).

7. Investigation — Local Police Out of Their Depth

• The local PD was unprepared; Grand Rapids eventually called in the FBI, who ran a sting on the suspects ([26:01], [52:33]).
• Quote: “The Grand Rapids cops are like, we might be just the tiniest bit out of our element here. We’re gonna call in the FBI for help.” (Jillian, [52:33])

8. The Underworld and the Sting Operation

• After a decade of dead ends and wild goose chases, things heat up in 2017:
  • A retired Secret Service agent tries to broker a reward for the slippers.
  • A middleman tries to ransom them for a $1 million reward (which didn't exist; the actual reward was $200k) ([51:29]).
• An undercover FBI operation in 2018 results in the retrieval of the slippers, after a dramatic meeting at an art gallery ([53:43]).

9. The True Thieves: Jerry and Terry

• After several false leads, the real thieves are revealed: two aging mobsters, Terry and Jerry—now both dead or on their deathbeds ([60:38]).
• Heist Recap: They smashed the case, took the slippers in 30 seconds, stashed them in a garage soffit and later buried them, all in Grand Rapids. The slippers sat in evidence for years after recovery ([61:10]–[57:52]).

10. The Auction and Modern Value

• By 2024, Shaw is allowed to re-purchase the slippers for the $800k insurance payout and auctions them off for $28 million ($32.5 million after fees), setting a world record for a piece of movie memorabilia ([63:09]–[64:06]).
  • Quote: “Ladies and gentlemen, the ruby slippers just sold for $28 million.” (Auctioneer, [64:06])
  • Hosts speculate the heist actually increased their value, and laugh that the new owner is probably Elton John or another (closeted) wealthy gay ([66:36]).

Notable Quotes & Memorable Moments

• On Museum Negligence:
  “Everybody, including the guy who donated the slippers, is 100% at fault.” (Patrick, [34:38])
• On the Museum’s Security Plan:
  “If your child is running around a museum with million dollar artifacts in them, making the emergency alarm go off that many times, you’re the problem.” (Jillian, [34:15])
• On the Auction:
  “All bids in now… $28 million. Ladies and gentlemen, the ruby slippers just sold for 28 million.” (Auctioneer, [63:52])
• On Queer Culture and The Wizard of Oz:
  “I swear to God, it’s almost homophobic how few gays there are and by how few, I mean zero.” (Jillian, [10:12])
• On Memorabilia:
  “They say that this auction invented the word memorabilia. Like, that’s wild.” (Jillian, [43:27])

Timestamps for Key Segments

• Start-of-Recap & Main Theme: [01:42]
• Hosts Critique Documentary's Lack of Queerness: [02:42]
• Judy Garland's Troubled Childhood: [12:34]
• Wizard of Oz Cultural Impact Discussion: [16:06]–[18:23]
• Theft Details & Security Failings: [31:25]–[35:13]
• Insurance Lawsuit & Payout: [37:42]–[39:02]
• Museum Director Disables the Alarm: [33:09]
• Discovery & FBI Sting: [52:33]–[54:27]
• True Thieves Revealed ("Terry and Jerry"): [60:38]–[61:16]
• Emotional Return & Auction: [63:09]–[64:40]
• Record-Setting Sale of the Slippers: [64:06]
• Speculation on the New Owner: [66:28]–[66:42]

Final Thoughts & Episode Tone

Jillian and Patrick keep the mood light, irreverent, and unfiltered—as always. Their deep dives into Wizard of Oz lore, honest critiques of true crime documentaries, and recurring inside jokes (where’s Jinkx Monsoon??) maintain the signature TCO balance of comedy and empathy. They delight in nostalgia, lament the gaps in the documentary—especially the absence of LGBTQ+ perspectives—and wrap up with their excitement over the next episode, promising a candid chat about a high-school catfishing doc.

If You Only Listen to Segments

• Cultural significance & Judy Garland critique: [12:34]–[18:23]
• Heist & Security breakdown: [31:25]–[39:02]
• Auction & modern value of the slippers: [63:09]–[64:40]

Next up: "Unknown Number: The High School Catfish"
The hosts tease a heated conversation on the controversial doc and promise to ask tough questions.

Summary prepared by:
Podcast Summarizer GPT — for your TL;DR true crime obsession