To Catch a Killer

Italy Closes In on Notorious Mafia Boss

Will the Sicilian Mafia’s most-wanted don evade capture once again?

08.04.15 4:47 PM ET

By any standard of measure, Matteo Messina Denaro is a very, very bad man. The Sicilian mob boss, nicknamed Diabolik, is said to have learned to fire a pistol he received as a gift on his 14th birthday and started his formal killing career at the age of 18 when he shot a man as part of his initiation into his father’s clan. “I could fill a whole cemetery,” he supposedly bragged to his friends upon his 50th murder. The last known hit he personally made was in 1993, when he famously killed a rival mobster on the orders of the Sicilian mob’s kingpin at the time, Toto' Riina. When the rival’s pregnant girlfriend pleaded for her own life, Messina Denaro put down his gun and strangled her to death. 

That year he also allegedly orchestrated a trio of bombings against museums and churches in Florence and Milan that killed 10 people and injured more than 90. At the time of the bombings he had already been in hiding for nearly a year, forced underground in the wake of the murders of Sicilian anti-Mafia prosecutors Paolo Borsellino and Giovanni Falcone, who were assassinated in separate incidents.  

Messina Denaro, now 52, is thought to have taken over the Cosa Nostra Sicilian Mafia leadership in 2006 when Bernardo Provenzano was famously captured in a tiny farmhouse from which he had been running the mob for decades. The FBI considers Messina Denaro one of the their most important fugitives as well, crediting him as one of the world’s superpowers in the global drug trade.  

Now, after more than 20 years in hiding, it would seem the noose is finally tightening around Messina Denaro.

This week, Italian authorities arrested 11 of Messina Denaro’s closest associates, including three men over the age of 70, after unraveling the network by which the boss apparently commands a criminal army of more than 1,000 people. Despite the fact that Messina Denaro is estimated to be worth more than $2 billion thanks to the Cosa Nostra’s lucrative deals with South American drug cartels, his lackeys apparently used “sheep code” to communicate rather than high-tech equipment. According to Renato Cortese, an anti-Mafia police official who announced the arrests, the associates would say things like, “I put the ricotta cheese aside for you, will you come by later?” when Messina Denaro’s minions had placed the traditional pizzini, or tiny handwritten messages wrapped in sticky tape, under a rock at a Sicilian sheep farm. “The hay is ready” meant there was dirty work to be done. “Time to shear the sheep” meant they needed to meet to discuss how to disseminate the information.

Now with Messina Denaro’s key contacts in the can, police hope they can smoke out the fugitive, whose 22-year disappearance remains a black eye on the Sicilian anti-Mafia force. More than three times in the last five years, police have homed in on an area where they thought he might be hiding, only to find it empty. Last year, Sicilian police seized €20 million worth of assets including olive groves, Messina Denaro’s stake in 43 companies, and nearly 100 properties. They also arrested his sister and 30 others known to have done business on his behalf.   The authorities have used drones, heat sensors and undercover officers to try to find him, but he has so far remained well hidden.

But it wasn’t always that way. For years he was spotted driving one of his many Porsche sports cars around Trapani, Sicily, where his clan is based. He also fathered a number of children in order to keep his blood line alive, including a daughter, Luciana, who lives in London and who is said to be marrying a Briton named Gordon next month. He is also reportedly a video-game junkie, insisting on the latest versions and equipment, which would imply that perhaps he enjoys some element of comfort wherever he may be. And police say that he was so confident in the early days of his exile he even flew to to Barcelona, Spain, to have laser surgery to correct his myopia despite the fact that he was wanted for murder and had been handed down multiple life sentences by the courts.   

Wiretaps gathered during the investigation that led to this week’s arrests show that Messina Denaro might be losing his power grip and may even be vulnerable to a turncoat betrayal. In transcripts distributed by police, two men recount their boss’s frustration that the “younger generation just disappears with no respect.” Italian press also reported that authorities are searching for a local priest who apparently visits the fugitive to offer him spiritual guidance and an unnamed woman who apparently offers him other comforts. Whether these methods eventually trip him up or if he continues to be the “one that got away,” there is little doubt that he feels the heat. 

“He feels the scorched earth around him,” Renato Cortese, head of central operations for the Anti-Mafia police in Sicily, said on Tuesday. “There is no such thing as an interminable fugitive, because eventually, for all there is an end. Now it is only a matter of time and dedication on our part to catch any error on his part.”