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The Last Boss? Why Matteo Messina Denaro May Mark The End Of Sicily's Old School Mafia

Arrested Monday in Palermo, Messina Denaro was the son of a mobster and successor of Sicily's notorious boss of bosses. He had been on the run for 30 years, trying to transform Cosa Nostra into a modern criminal enterprise — with only partial success.

Photo of Messina Denaro taken away by police

Matteo Messina Denaro led away by Italian Carabinieri police on Monday

© Carabinieri/ANSA via ZUMA
La Stampa Staff

-Analysis-

PALERMO — It was 30 years ago, almost exactly to the day, January 15, 1993, when Totò Riina, then the undisputed head of the Corleone clan, was captured in Palermo. On Monday, it was the turn of Matteo Messina Denaro, now 60 years old, who has occupied the same place as "boss of bosses" of the Sicilian Mafia, who was tracked down and arrested in the same city.

Tracing back in time, Messina Denaro began his criminal ascent in 1989, around the first time on record that he was reported for mob association for his participation in the feud between the Accardo and Ingoglia clans.

At the time, Messina Denaro's father, 'don Ciccio', was the Mafia boss in the western Sicilian city of Trapani — and at only 20 years of age, the ambitious young criminal became Totò Riina's protégé. He would go on to help transform Cosa Nostra, tearing it away from the feudal tradition and catapulting it into the world of would-be legitimate business affairs.

For 30 years he managed to evade capture. He had chosen the path of ‘essential communication’: a few short pizzini - small slips of paper used by the Sicilian Mafia for high-level communications - without compromising information by telephone or digital means.

“Never write the name of the person you are addressing," Messina Denaro told his underlings. "Don’t talk in cars because there could be bugs, always discuss in the open and away from telephones. Also, take off your watches.”


He had been a fugitive since the summer of 1993, when in a letter written to his then-girlfriend, Angela, after the Mafia massacres in Rome, Milan and Florence, he began his life as a Primula Rossa (or "Scarlet Primrose," the term Italians use for top Mafia fugitives). “You will hear people talk about me,” he had written to her, hinting that he was aware that his name would soon be associated with serious acts of bloodshed. “They will paint me as a devil, but they are all lies."

Thirty years on the run, two kids

Considered until Monday the last major primula rossa of the Sicilian mob, Messina Denaro had gone missing soon after the capture of Totò Riina, nicknamed ‘the Beast.’ And while the forensic police took charge of updating and aging the youthful image of the boss, his billionaire empire was dismantled and seized piece by piece.

This is how his chain of protection and financing would ultimately be dismantled.

This is how the myth would be demolished of a godfather who managed infinite power but lived like a ghost.

His invisibility did not prevent him from becoming a father twice. Everything is publicly known about a daughter: her name, her mother and what led her to separate her life from the heavy shadow of a father she may never have met. She spent her childhood and adolescence in her grandmother's house, then changed residence with her mother: it is not easy to live with the stress of searches, checks and police raids.

What little is known of the son, however, that has leaked out from the wiretaps, is that his name is Francesco, like the old patriarch of the dynasty, and he was born between 2004 and 2005 in that part of the Province of Trapani, between the towns of Castelvetrano and Partanna, where Matteo Messina Denaro built his economic and criminal power.

Young Messina Denaro

photo of young Messina Denaro in sunglasses

An undated photo of Messina Denaro from his youth

Who was the real Diabolik?

Careful to manage his fugitive status, and to protect it with a host of associates, one of the world’s most wanted bosses also left behind a reputation as a relentless player in Ray Ban sunglasses, designer shirts and a smart casual style. Behind this faded image, a trail of legends: a playboy, a lover of Porsches and gold Rolexes, a video game maniac and an avid consumer of comic books. One series, Diabolik, was the source of his nickname, along with the moniker 'U siccu, Sicilian dialect for ‘the skinny one.’

He moved comfortably between criminal ferocity and political pragmatism.

Even in his nicknames, Matteo Messina Denaro embodied the double face of a leader capable of combining the traditional and family dimension of the Mafia with its more modern version. This godfather, like some but not all of his predecessors, moved comfortably between criminal ferocity and political pragmatism.

This is why he was considered the heir of not only his father Don Ciccio, who died as a fugitive in 1998, but also of Bernardo Provenzano, chief of Cosa Nostra after Riina’s arrest, who was captured in 2006 in Corleone, Sicily. When his father died, Matteo Messina Denaro had already been on the run for five years, even before he was involved in the investigations into the worst Mafia crimes of the 1990s.

Since then, Diabolik had always managed to escape the authorities, sometimes with the kind of acrobatics worthy of the impregnable comic-book character who lent him the name. A bounty of one and a half million euros had been placed on him, but in order to isolate him, the investigators had tightened the network of supporters into a deadly pincer.

Not even his family members were spared: his sister Patrizia, arrested and accused of running an extortion ring, his brother Salvatore, his brothers-in-law, and even a nephew, along with many of his confidants, consisting of often unsuspected figureheads, who have run into repeated asset seizures.

Falcone, Borsellino and his legacy

The ‘ghost’ of Messina Denaro was chased by a mountain of arrest warrants and life sentences for mafia association, murder, bombings, possession and transport of explosives. His hand was implicated in some of the most serious criminal events of the last 30 years, starting with the 1992 assassinations of Giovanni Falcone and Paolo Borsellino, the two leading prosecuting magistrates of the so-called ‘Maxi Trial’ that convicted some 475 mobsters.

Afterward, he was convicted of having ordered to kidnap, kill, and dissolve in acid the 12-year-old son of one of his ex-associates who had decided to reveal important information about the killings of the two judges. Messina Denaro brushed it off, once boasting that he had “killed enough people to fill a cemetery”.

Nevertheless, even though his reputation as a ruthless man is recognized, some doubts have crept in on his real ability to rebuild, after the arrests of Riina and Provenzano, the hierarchical structure of Cosa Nostra eroded by arrests and a process of fragmentation.

Matteo Messina Denaro was a boss who helped remake Cosa Nostra for a new century, but couldn't manage to avoid the same fate as the godfathers who came before.

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-Analysis-

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