Matteo Messina Denaro, Italian mafioso, 1962-2023

As Sicily’s Cosa Nostra waged a bloody war against the Italian state in the early 1990s, Matteo Messina Denaro sat on the Mafia’s ruling council, or Cupola, helping to greenlight and plot contemporary Italy’s most heinous crimes.  

But after his ruthless Mafia mentor’s 1993 imprisonment, Messina Denaro went underground, living for the next 30 years as Italy’s “most wanted”: a luxury-loving, womanising fugitive, who shifted his focus — and Cosa Nostra’s — from warfare to wealth.

Convicted in absentia of orchestrating the devastating 1992 car bombings that killed celebrated anti-Mafia prosecutors Giovanni Falcone and Paolo Borsellino, Messina Denaro was sentenced to multiple life terms in prison. Yet when he was finally arrested in January at a private medical clinic in Palermo where he was undergoing cancer treatment using a fake identity, his failing health kept his time in custody brief. 

Messina Denaro, who died this week, was born on April 26 1962, the scion of a Mafia family in western Sicily. His father, Francesco, was said to have run a lucrative business in the illegal sale of antiquities plundered from the region’s many ancient Greek and Roman sites, and was the head of the local Mafia clan.

The elder Messina Dennaro was a loyalist of Salvatore “Totò” Riina, the notoriously brutal Cosa Nostra boss who took control of the criminal organisation in the early 1980s after an internecine Mafia war in which all his internal rivals — and their extended families — were slaughtered.

As a teenager, Matteo Messina Denaro, nicknamed “U Siccu’” or “the skinny one”, was taken into Riina’s inner circle as a trusted protégé, according to Lirio Abbate, author of several books on the Mafia, including a biography of U Siccu. 

When Riina declared war on the Italian state in 1992 — to avenge the criminal convictions of hundreds of mafiosi in the high-profile “maxi trial” based on the investigations of Falcone and Borsellino, his protégé was among the tight-knit coterie of mob bosses who helped organise the savage attacks.

Along with the assassinations of the two magistrates, Messina Denaro was also convicted for approving the murder of the young son of a Mafia turncoat and plotting a series of five deadly bomb attacks in 1993 at cultural sites in Rome, Florence and Milan, such as the Uffizi Gallery and two of Rome’s most venerated churches.

Once in hiding, though, Messina Denaro adopted a “submersion” strategy, eschewing the violent attacks on officials and public sites to return to the mob’s original vocation: moneymaking. 

“He changed Cosa Nostra and his life,” said Abbate. “He set his own Mafia strategy based on business. He didn’t take Riina’s projects — the attacks and the war against the state — forward.”

Italian anti-Mafia investigators believe Messina Denaro helped modernise the Mafia’s business operations, investing in a range of companies, including a Sicilian supermarket chain, alternative energy, construction and real estate.

While Messina Denaro was often considered the Mafia’s de facto leader after Riina’s longtime second-in-command was arrested in 2006, Abbatte said he never held the formal role as “boss of bosses”, and operated more as an éminence grise. He never married — unusual in family-oriented Mafia circles — but had many lovers.

The fugitive’s ability to elude arrest, aided by his vast wealth, was legendary, and some speculated that he had left the country, undergone face-changing plastic surgery or even died in secret.

But in the past few years, the authorities gradually unravelled his elaborate logistics support network, seizing his valuable assets and arresting numerous people suspected of shielding the fugitive, including his sister and other relatives, and two police officers who were later convicted of helping him. 

Prior to his arrest, Messina Denaro had been living in apartment in a remote village in western Sicily, and had several other hide-outs nearby — including one decorated with a poster from the Hollywood Mafia film The Godfather.

Though the authorities hoped the ailing mafiosi might reveal secrets about the Cosa Nostra’s ties to politicians and business people past and present once in jail, prosecutors said he maintained his vow of silence, or omertà.

Abbatte said that Messina Denaro’s ability to expand his wealth and live undetected for three decades was a potent example for the Cosa Nostra.

“The Mafia has learnt — thanks to Messina Denaro — that it can keep doing business invisibly, without bloodshed,” the author said. “If you don’t see the blood, you forget the Mafia exists.”