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Italian mafia boss Matteo Messina Denaro, the last of a generation of Cosa Nostra gangsters that waged a bloody war against the state in the 1980s and 1990s, has died in custody just eight months after his arrest.

Following 30 years as Italy’s most wanted man, Messina Denaro was captured in January at a private medical clinic in Palermo, a longtime mafia stronghold and the centre of its business activities, where he had been undergoing chemotherapy for colon cancer using a fake identity. 

His whereabouts had long been the subject of intense speculation — including that he had fled overseas, undergone plastic surgery to change his facial appearance or even died in secrecy.

Yet, at the time of his arrest he was found in a small town in the south-western Sicilian province of Trapani, just a few kilometres from his home town of Castelvetrano, protected by a tight network of friends, family and supporters, and with a movie poster from the Hollywood film The Godfather on his wall.

The mafioso died after slipping into an “irreversible coma” in the prison ward of a hospital having recently been transferred from a maximum security unit as his health deteriorated.

Italian state radio said Messina Denaro “took with him his secrets” about the Cosa Nostra to the grave, maintaining his vow of silence, or omertà, and refusing to co-operate with prosecutors, during his months in prison.

At the height of his activity, Messina Denaro was a member of the ruling council or Cupola of the Cosa Nostra, the Sicilian organised crime group that waged a war against the Italian government, terrorising the island of Sicily and the Italian mainland with attacks on prominent figures and high-profile cultural sites. 

He was convicted in absentia of multiple killings in some of the Cosa Nostra’s most spectacular crimes, including the 1992 assassinations of anti-mafia prosecutors Giovanni Falcone and Paolo Borsellino — murders that had led Italians to doubt the state’s ability to keep them safe.

Messina Denaro, wearing glasses and a high-collared sheepskin jacket
A police mugshot of Messina Denaro © Italian Carabinieri/AFP/Getty Images

Messina Denaro was also involved in planning a series of deadly bombings in 1993 at a famous church in Rome, Florence’s Uffizi Gallery and in Milan, for which he was also convicted in absentia and sentenced to life in prison.

The late mafioso was a disciple of the Cosa Nostra’s most brutal 20th century boss, Salvatore “Toto” Riina — who was arrested three decades ago. He took over the daily running of the organisation after Riina’s arrest in 1993, eventually reaching the top of the mafia hierarchy as the so-called “boss of bosses”. 

But by then, Cosa Nostra’s power had been considerably eroded, as the increasingly heinous nature of its crimes finally prompted a determined state crackdown and the arrest of its leaders. 

Today, the Sicilian Cosa Nostra has been overshadowed by its Calabrian-based rival, the ’Ndrangheta, whose global drug trafficking network is the subject of intense law enforcement surveillance. 

In May, police in multiple European and Latin American countries seized 23 tons of cocaine worth an estimated €2.5bn, and arrested about 150 people, in a major strike against the ’Ndrangheta.

However, prosecutors say the Cosa Nostra — though far diminished from its terrifying heyday — remains a threat in Sicily, where it looks for lucrative business opportunities, including involvement in public works, drug trafficking and online gaming.

In a report issued this month, the National Anti-Mafia Directorate warned that new leaders were beginning to emerge, vying to establish their pedigree and authority over the Cosa Nostra, even as an older generation of leaders returned from prison after decades and attempted to re-establish their own power.

“The mafia is proving to be attractive for the young generation, not only for young men that come from mafia families,” the report warned. “However, there would be no shortage of attempts by elderly men of honour, recently freed, to regain their position.”

Additional reporting by Giuliana Ricozzi in Rome

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