Season 1
From the Travel Journal: The Great Palermo Art Heist

What do the Mafia, the revered painter Caravaggio, and the confessions of a Catholic priest have in common? The biggest unsolved art heist in Italy’s histroy.


This week, Passport headed to Palermo, Sicily to find out how a brave, new crop of chefs and restaurant owners are taking on one of the most powerful and deadly forces the island has ever seen – and that’s saying something on an island that’s been invaded as many times as Sicily – the Costa Nostra, aka the Sicilian Mafia.

But food isn’t the only cultural treasure the Mafia has set its sights on controlling and exploiting. And during our research we stumbled on one of the greatest art mysteries of the 20th century – a caper that involves the most powerful Mafia bosses of all time, a revered painter who was himself a criminal, and an international art hunt that was given new life by the confessions of a priest. 


It was a dark and stormy night (no really, it was) on October 17th, 1969. Thunder clapped and rain came down in buckets over the capital of Palermo, Sicily. The storm created such a ruckus, it would have been hard to hear someone talking if they were standing just a few feet away. And so, it would have been especially hard for anyone to hear as two men quietly slipped through a window and into the Oratory – or church – of San Lorenzo. 

When the storm passed, Maria Gelfo made her way to the Oratory. Maria, her sister, and her daughter, Antonella, lived at the church and were its caretakers. Antonella heard a loud wail from her mother and ran to the Oratory to see what had happened.

At the front of the altar was an empty frame. A frame that, for 360 years, had held perhaps the most treasured and valuable painting in all of Palermo: Michelangelo Merisi da Caravaggio’s Nativity with St Francis and St Lawrence, otherwise known as The Nativity

The painting has never been seen again. It remains one of the greatest art mysteries of the 20th century. In fact, it’s still listed as #2 on the FBI’s most wanted stolen art list (yeah that exists). But as an old Sicilian Proverb goes: 

Cui cerca, trova; cui sècuta, vinci.

Who seeks, finds; who perseveres, wins. 

When investigators arrived at the Oratory, they surveyed the clues at the scene; clues that people are still pouring over to this day for new insight or angles. 

First, there was the window the thieves had obviously climbed through. It had street-level access. In the weeks preceding the painting’s disappearance, Antonella’s mother had actually had several suspicious run-ins with strangers wanting to be let in to see the painting. These encounters spooked her enough that she had requested greater security for the window. Her requests were ignored.

Next, there was the missing carpet. Investigators surmised that the carpet was used to roll up and conceal the painting as the thieves made off with it. This finding worried those investigators who knew anything about old paintings. Rolling up a painting that old in a carpet could result in the paint cracking and disintegrating. If that was true, then this heist was the work of amateurs and the painting was in great danger.


But then, in contrast, was the third clue: the empty frame. Not a stitch of canvas was left. Whoever had cut the painting out had done it so professionally and so meticulously that they literally hadn’t missed a stitch. During a presentation on the lost masterpiece, the president of the Palermo cultural association, Amici dei Musei Siciliani, said the theft had to be the work of professionals. The extraction, according to him, was undertaken “without leaving a milligram of paint behind,” and was an act of “surgical precision.” Whoever did it knew their way around old paintings and had also had ample time to study The Nativity to understand exactly how to extricate it from its frame. This suggested someone with know-how – or someone with the resources pay for know-how. 

But no matter who investigators questioned and what clues they followed, they got nowhere. The Nativity, the prize of Palermo worth an estimated $20 million dollars, was gone. 

Investigators around Europe began keeping their eyes open for news of a big sale on the stolen art market. With a painting that valuable, someone was going to want to cash in.


In the US in 1969, as copies of The Godfather – Mario Puzo’s mafia masterpiece – were first hitting bookshelves, another masterpiece was in peril. 

It was several weeks after The Nativity had gone missing that Monsignor Benedetto Rocco, the parish priest of the Oratory, received the first letter. It was short and sweet: we have the painting and if you want to make a deal, place this advertisement in Giornale di Sicilia. The Giornale was (and still is) the most popular newspaper on the island and the message was from the Costa Nostra (which means “Our Thing”), Sicily’s all-powerful mafia. The advertisement in the newspaper was meant to be a signal to the Costa Nostra that the church was ready to negotiate for the painting. 

Rocco took the letter to the minister of cultural affairs. When the mafia is holding a priceless piece of art for ransom, you don’t ask too many questions. They published the ad. But Rocco also went to the police. 

The mafia weren’t pleased. Another letter arrived for Rocco. This time, it contained a slice of the painting. It was classic mafia – except instead of an ear or finger, it was a precious piece of canvas touched by one of Italy’s true masters. They demanded again that they place an ad in the paper to start negotiations. But this time the cultural minister refused. And now he went to the police, too: to report Rocco. 

The bible is full of messengers – celestial and real – getting caught in the crossfire. Now Rocco was one of them. Instead of following up on the information Rocco had provided them, the Palermo police were now investigating Rocco himself in the theft. Precious weeks ticked by as the police focused on the priest. And the painting slipped through their fingers. The letters stopped. It was radio silence. Suspiciously, Rocco’s initial statements to the police also went missing and have never been found. Years later, Rocco recorded his account of what had happened to a documentarian, who then shared it exclusively with the Guardian

Rumors began to develop in the absence of real information. The painting had been stolen by amateurs who’d accidentally destroyed it and then burned it to get rid of the evidence. The painting had been stolen by the mafia and stored in an old barn where it had been eaten by rats. The painting had been stolen by sophisticated art thieves, but when the Costa Nostra found out, they paid the art thieves for the painting as a sign of their total power in Palermo. It was being used as a welcome mat in a famous mafioso’s house. And on and on.  

Some might have thought Caravaggio was turning in his grave. Well, those people don’t know Caravaggio.


History is littered with stories of mad artists, rebels with a paintbrush, and the bad boys of sculpture. But even among excentrics and wild ones, Caravaggio is in a class of his own. He was born Michelangelo Merisi in Italy in 1571. After both his parents died of the plague when he was a child, he moved to Rome and started selling his own paintings around 1595. He quickly made a name for himself as a bold, fresh painter – and as drinker, gambler, and man prone to outbursts of violence.

Yes, had Caravaggio been born 360 years later, he probably would have BEEN in the mafia. In fact, the entire reason the painting of The Nativity – that sweet, innocent baby-in-a-manger scene – even hung in the Oratory in the first place was because of murder. Caravaggio was a mad man. He’d been on trial no less than 11 times in his life. 

Some of his greatest hits:

  • He carried a sword without a permit aka Concealed Stabby
  • He assaulted a man with a stick aka Stick it to the Man
  • He threw a plate of artichokes at a waiter aka Have a Heart

And my personal favorite:

  • He was sued for libel by a rival painter named Baglione. Baglione said Caravaggio had hired assassins to try and kill him. Caravaggio balked and doubled down, writing satirical poems about Baglione’s terrible (according to Caravaggio) art and passing them out in their artists’ village. It’s not really fit to print, but let’s just say he suggested that people use Baglione’s artwork after going to the bathroom and commented on a certain appendage of his. You can read an excerpt at your own risk here. Savage. Caravaggio lost his libel suit (not hard to see why) and spent a few weeks in jail. But he wasn’t done yet. 
  • Finally, he just flat out murdered a man. And it wasn’t any old murder. Rumor is, he and another man were fighting over a prostitute when Caravaggio attempted to castrate the man. But Caravaggio missed with his knife and instead, severed his femoral artery and the man bled out. Cool. 

That was the last straw. Cool paintings and birthing an entirely new style of baroque painting aside, the pope called for Caravaggio’s capture and death. Caravaggio went on the run; through Rome, Naples, Malta, and Palermo. And it was in Palermo, while on the lam from castration-turned-murder charges that Caravaggio painted the baby Jesus so beautifully. After several months in Sicily, he became convinced his enemies had found him and were after him, so he left the painting there and he fled back to the mainland. And there the painting stayed for 360 years. 

Coincidentally, Caravaggio’s death was as dramatic as his life and is still shrouded in conspiracy and mystery. He was on the run after being horribly disfigured in a fight in Naples when he supposedly contracted a fever of some kind and died. But there are those who believe he was murdered or that he suffered from lead poisoning from all the lead-based paints used in his day. 

Anyway back to this mad man’s missing painting.


Nobody had heard a word about The Nativity in Palermo and people had all but forgotten about Monsignor Rocco’s statements and the letters. But not Monsignor Rocco. The year after the theft, in 1970, he’d heard from another priest that the mafia indeed had the painting. The priest even showed Rocco a picture of the painting hanging in someone’s house. Which mafioso, nobody knew for sure. Rocco tried to take his new information to the police, but we know how that went by now. Nothing happened. Another Sicilian Proverb comes to mind: 

‘Ntra greci e greci nun si vinni abbraciu.

There’s honor among thieves.

The police clearly were not interested in disrupting the criminal (and profitable) activities of the Costa Nostra. Fifteen years passed. It was now the mid-80s and stuff was about to get real for the Sicilian Mafia. An ambitious, totally stable genius named Rudolph Guiliani had just been named US Attorney in New York and wanted to make a name for himself. And to do it, he was going to take the mafia down.

One of his biggest fishes was a man named Gaetano Badalamenti. Badalamenti hailed from just outside Palermo and was head of one of the most powerful arms of the Sicilian Mafia. In the 80s, he’d moved to the US and now ran something the Feds would come to call the “Pizza Connection”. It’s like the French Connection, but with pizza. Raw ingredients for heroin came into Sicily via Turkey and the Middle East. Secret Sicilian houses then turned them into heroin. And then Badalamenti used innocent-looking US pizza parlors as fronts, using them to smuggle heroin and launder mafia money. A slice of pie.  

It’s estimated that Badalamenti imported $1.65 billion dollars worth of heroin into the US through pizza parlors before Guiliani caught up with him. Badalamenti went down in 1984. Guiliani got his big fish. And as kingpins started to fall, some mafiosos began to turn while they still could. These rats… sorry, informants… were known as pentitos

And in 1989, a pentito named Francesco “Mozzarella” Marino Mannoia revealed to the famed Sicilian prosecutor Giovanni Falcone that he had stolen the Caravaggio. He was one of the two men on that dark and stormy night at the Oratory. Finally, confirmation straight from the pentito’s mouth. In our Passport episode this week, you can hear more about what happened to Giovanni Falcone during his dangerous and heroic battle against the Sicilian mafia in his hometown. Fair warning, it’s not pretty. 

“Mozzarella” said that the painting had been proudly displayed in the homes of mafiosos as a sign of their power and dominance. So where was The Nativity now? Show me the Caravaggio, Mozzarella.  But Mozzarella didn’t know. 

Another twenty years passed without any new leads or slices of canvas until May of 2018 when another pentito came out of the woodwork. Gaetano Grado, a former mafioso, revealed to Italian investigators that the painting had been held by none other than Gaetano Badalamenti – of the Pizza Connection. And that since his arrest and death (he died in prison in 2004) a member of his crime family had been put in touch with an art dealer in Switzerland. 

True Crime Maxims: When it comes to blond women being murdered, it’s always the husband. When it comes to stolen artwork, it’s always the Swiss. 

Investigators have since been scouring Switzerland hoping to find The Nativity. But… so far, no luck. The Swiss dealer the pentito named had since died. But the investigators did find a new clue that now points to the theory that the painting may have been traveled from Switzerland to Eastern Europe. Perhaps mad man Caravaggio’s masterpiece is hanging in a Ukranian mafioso’s house now. Maybe Rudy Guiliani can make a phone call.  

A replica of The Nativity now hangs over the altar at the Oratory of San Lorenzo, so you can behold its beauty. But just know that somewhere out there, someone else is looking at the real thing.

Image Credits:
Banner image: Piazza Pretoria, Palermo, Italy – Photo by Cristina Gottardi on Unsplash
Watercolour Streets: Photo by Linda Robert on Unsplash
Monsignor Benedetto Rocco testifies about Caravaggio’s Nativity:  Via The Guardian

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© 2018, Frequency Machine Studios.
© 2018, Frequency Machine Studios.