Transcript

Julia Benzavale (0:00)

We just spent 10 minutes talking to Gina Gershon.

Patrick Hines (0:02)

That wasn't. That was real.

Julia Benzavale (0:03)

That really happened. Hi. Julia Benzavale.

Patrick Hines (0:13)

Hello. Patrick Hines. And also Gina Grishon.

Julia Benzavale (0:16)

Just to tell you what happened real quick, we're at Borough House, the new studio that we're recording at. Gina Gershon was doing a podcast interview right before us. She came out and she was so nice.

Patrick Hines (0:25)

Like, she said hi. We weren't going to bother her, but we were right there.

Julia Benzavale (0:28)

She came out and said hello. We talked about Showgirls. We talked about Bound.

Patrick Hines (0:33)

And then I.

Julia Benzavale (0:34)

If you remember a couple of years ago when we did Class Action park and we did it on the road, we played the trailer for the documentary and I was convinced that Gina Gershon was in the Lazy River.

Patrick Hines (0:43)

Guess what? We have confirmation. It was not.

Julia Benzavale (0:44)

It was not her. She's like, I would never go to lazy. I was like, you know what, Gina Gershon, that absolutely tries.

Patrick Hines (0:49)

Yes.

Julia Benzavale (0:49)

Love it, fam. Don't forget to join us over in the Patreon if you want, like 500 full ad free bonus episodes. Listen. At our Hero Bell tier, we do this thing where we make special episodes just for them, where we cover things we can't really cover in the regular feed or the Patreon feed. So we're covering that documentary, Predators. Predators. It's the documentary about that show To Catch a Predator.

Patrick Hines (1:09)

Or is it? We have thoughts and feelings. It's a mess. But we did it for you, for the Hero Bells. So there you go.

Julia Benzavale (1:14)

Go check it out. And also what we're going to tell

Patrick Hines (1:16)

them about them, the Discord. We have a Discord server. It's really fun. There are lots of channels. Everyone's really nice.

Summary

True Crime Obsessed – Episode 490: The Dali Heist (From "True Crime Story: Smugshot")

Release Date: March 24, 2026
Summary by: True Crime Obsessed

Episode Overview

In this lively and irreverent episode, hosts Patrick Hines and Julia Benzavale recap the unbelievable true story of the "Dali Heist," as featured in "True Crime Story: Smugshot." Set inside New York's infamous Rikers Island prison, the heist centers on the theft of a genuine Salvador Dali painting – the surreal circumstances that put it there, the bumbling inside job by corrupt guards, and the ridiculous fallout. The hosts blend signature humor with thoughtful reflection on art, crime, prison corruption, and why art heists (almost) never go as planned.

Key Discussion Points & Insights

Meeting Gina Gershon (00:00–01:14)

The episode opens with excitement: the hosts met Gina Gershon at their new studio. Julia and Patrick briefly geek out, confirming she's as charming as they'd hoped.
Injects the familiar, friendly tone; sets up the energy for the episode.

The Dali Heist: Introduction (01:14–03:25)

Julia: “NYC’s famous or infamous jail of all places. Comes word of an art heist as surreal as the art itself.” (02:00)
The stolen painting: "Christ on the Cross" by Salvador Dali, gifted to Rikers in 1965.
Reenactment quote: “Oh shit. I looked at my wife and said, well, I'm happy we have a baby, but I'll see you in about 18 years because I think I'm going to jail.” (02:01)

How Did a Dali Painting End Up at Rikers? (03:25–06:49)

The hosts marvel and laugh at the absurdity: why did Rikers even have a Dali painting?
Julia's hot take: “I think that art should absolutely be in prisons. ... But they were taking it for granted, like we all knew there was a Dali painting at Rikers.”
The painting was originally installed in the dining hall but was moved due to damage from frequent fights (09:42).
Eventually put under glass in a “manned 24 hours” secure area with CCTV.

Prison Corruption & Context (05:53–06:49)

Patrick and Julia lament how quickly the documentary breezes by the horrific conditions at Rikers, saying its inhumanity is well documented.
“This is kind of like, we're not gonna talk about Judy Garland's horrible childhood. We're just gonna talk about the shoes.” (Patrick, 05:53)

The Players: Guards, Investigators, and Would-Be Criminals (06:49–12:11)

Michael Caruso: 27-year Department of Investigation veteran focusing on prison corruption.
George Sheehy: Guard with a "very, very dark side,” has a history of excessive violence but wasn’t fired – “everything but fired him.” (21:23)
Quote: “He has been written up for violence... so many times that they, ‘take everything away from him.’ And I'm like, George, they did everything but fire you.” (21:23)
Robert Whitman: FBI National Art Crime Team member; bemused by how amateurish the whole heist was.
Art expert Elliot King: “Everything about the Rikers theft is amateurish.” (11:29)

How The Dali Got To Rikers (12:11–18:05)

Backstory: In 1965, Dali agreed to teach an art class at Rikers (probably as a publicity stunt), then bailed, but sent a quick, original sketch as consolation.
The painting was placed in Gen Pop, inevitably damaged and disregarded.
A sign declared the work was worth $1 million, “almost baiting” its theft (18:05).
Narrator: “They basically flagged it... This is a very expensive painting that nobody is really paying much attention to.” (18:05)

"Not the Sharpest Knives": The Plot Unfolds (20:15–27:36)

Multiple Rikers guards are involved—led by Assistant Deputy Warden Benny and warden-level colleagues.
The fake painting: Guards recruited George Sheehy to recreate the Dali from a partial Polaroid. Result: a poorly sized, obviously fake dupe.
The plan's flaw: too many conspirators, all prone to panic and tattling. Everyone is wired.
Pena, a low-level guard: rushes to confess and blame the higher-ups (22:18).

Inside Job Shenanigans (27:36–44:46)

The theft: During a staged nighttime fire drill (a pretext that "never happens," 42:25), painting is swapped for the dupe.
Keystone cop comedy, with guards unable to open the protective case and failing to use a stapler to hang the fake (“Bang the stapler!” 44:16).
They forget to clear a stray plant from behind the glass and end up tossing the evidence (latex gloves, silver stapler) into the water (44:57).

Discovery and Downfall (41:46–47:15)

The swap is discovered almost immediately—one correctional officer prayed at the Dali daily and noticed the fake.
NYPD and investigators search Benny’s mother’s house (and must return after realizing evidence on tape mentions hiding the painting in the ceiling, 45:22).
Investigators also find stolen Rikers materials (logbooks, blankets) at the home.

The Value of Stolen Art (32:02–36:47; 54:01–58:54)

Art crime investigator Robert: The myth of the “rich villain with a hoard of stolen art” is pure Hollywood. “[In] 30 years of investigations—never saw that happen." (32:04)
Stolen art’s real value: “Things are valued at, like, 35 million, and then they're sold for 200 grand…proving that nobody cares about stolen art. Me most of all.” (Patrick, 33:05)
The Mona Lisa only became famous after being stolen; “With the Rikers Dali, I would just expect it to be worth more because of the story behind it.” (Elliot King, 34:35)
Art’s value is subjective; it can’t always be formally established, impacting criminal sentences.

The Trial: Absurdity in the Courtroom (52:26–58:54)

Defense’s strategy: Devalue the painting so the theft is a misdemeanor, not a felony.
Joe Taina (Defense Lawyer): “If it's below $25,000 … it's a misdemeanor. Which is a far cry from 10 to 15 years in jail.” (52:34)
Star appraiser pleads the Fifth on the stand when grilled by Taina, to the hosts' amusement (54:54).
A defense expert, former Dali student, argues the painting was rapidly sketched, already deteriorated from poor materials and conditions—so not especially valuable.

The Verdict: Nobody Cared (58:59–61:10)

Trial transcripts are inconclusive; both sides spin the wiretap evidence in their favor.
Jury finds “Benny” (assistant warden, alleged ringleader) Not Guilty.
Patrick: “The jury eventually says in the paper, it was a Friday. No one really gave a shit about the art or any of this.” (60:13)

Reflections: The Absurdities of Art, Justice, and The Heist (throughout, but esp. 60:35–61:12)

The painting’s whereabouts remain unknown—possibly lost in a storage locker (“some lucky son of a bitch on Storage Wars,” 47:34).
Final tones: Dali himself would likely have loved the outrageousness and absurdity of the whole situation. The painting, created as an afterthought, inspired a legacy far beyond its intended purpose.
Patrick: “At the end of the day...this is just so Dali.”

Notable Moments, Quotes & Timestamps

[02:01] Voice Actor: “I looked at my wife and said...I'll see you in about 18 years, because I think I'm going to jail.”
[04:12] Julia (on last names): “As an effeminate boy named Pat in the era of Pat on Saturday Night Live, like, I see you, Sheehy, and I feel the pain.”
[09:18] Detective Mike: “I looked at it and I said, quote, ‘This is a shit show.’”
[18:05] Narrator: “Flagged it as expensive...almost baits people into thinking...maybe this is an opportunity.”
[21:23] Patrick: “He has been written up for violence...so many times that they, ‘take everything away from him.’ And I'm like, George, they did everything but fire you.”
[24:42] Detective Mike: “He was all over the map, talking 100 miles an hour. ...We did it. We didn’t do it...I had to do it because it was a boss asked me to do it...”
[32:04] Elliot King / Art Expert: “Theory that some rich Saudi prince...never saw it happen in 30 years of investigations.”
[44:16] Voice Actor: “I don't know how to use the stapler.” / [44:18] "Just bang the stapler. Bang the stapler."
[54:54] Julia: “She pleads the Fifth. Really a bad look. This is my Real Housewives. Like, I'm not a Housewives person, but the art heist shit is my housewives.”
[60:13] Patrick: “The jury eventually says in the paper, it was a Friday. No one really gave a shit about the art or any of this.”

Structure of the Heist: Quick Reference Timeline

| Time | Event | |---------------|-------------------------------------------------------------| | 1965 | Dali skips prison art class, sends consolation sketch | | Late 20th C | Painting moved to secure area after being damaged | | 2003-2005 | Plan hatched by guards amid Rikers’ ongoing dysfunction | | The Heist | Fake dupe swapped in during staged fire drill; botched | | Immediately | Painting swap is discovered by devoted, daily-prayer guard | | Investigation | Guards panic, everyone wires up, confesses, covers tracks poorly | | Aftermath | Painting believed hidden at Benny's mom's, then lost | | Trial | Defense successful—painting juried as low value, Benny acquitted |

Podcast Tone & Community

Hosts balance wit, pop culture references, and insightful critique about the justice system, art value, and the particular absurdity of this crime.
Patrick and Julia regularly riff, tease, and confide hypotheticals (“If I found this in a storage locker, I’d keep it a year, then return it…” 48:08).
Signature blend of sass, skepticism about institutional motives, and empathy for art (and even some for the criminals’ stupidity).

For Further Listening

Next up: “The Missing Millionairess” – a double installment on Hulu.
Join the TCO Patreon (“over 500 full ad-free bonus episodes!”) for extra recaps, including thoughts on predators, unsolved mysteries, and reality favorites.

For anyone who hasn't listened:
This episode is a romp through one of the most ill-conceived art heists in American crime, told with side-splitting banter and genuine curiosity about art, justice, and why people make the choices they do—even when they’re (hilariously) disastrous.