A FAST-living playboy with an appetite for supercars and gorgeous women, Matteo Messina Denaro knows how to stand out from the crowd.

Yet for nearly 30 years, the man often called the Sicilian mafia’s ‘boss of bosses’ has somehow evaded a frenzied manhunt – once joining El Chapo and the successor to Osama Bin Laden in the list of the world’s 10 most wanted fugitives.

10 Matteo Messina Denaro, the Sicilian mafia's 'boss of bosses'. is one of the world's most wanted fugitives Credit: Italian police via AP

Last month, the trial of a billionaire windfarmer shone the light back on the mob boss – nicknamed ‘Diabolik’ after an Italian cartoon thief – as he was was jailed for aiding a huge network of tycoons bankrolling Denaro, 57.

The crook - said to have been involved with the murder of a child strangled to death and dissolved in acid - is wanted by police for over 50 murders, and chillingly once boasted: “I’ve filled a cemetery all by myself.”

A notorious womaniser, Denaro is thought to had a hareem of lovers and left a string of illegitimate children behind.

So how has he slipped through the net for so long – all the while controlling a global criminal syndicate worth £115billion?



Strangled pregnant woman to death

Born into the Italian underworld, Denaro built his notorious criminal name through a series of ever-more extreme murders and atrocities.

The son of the influential mafia 'capo' (captain) Francesco Messina Denaro, he quickly rose through the ranks of the Sicilian Mafia – also known as the Cosa Nostra – learning to use a gun at 14 and committing his first murder at 18.

The Armani-flaunting womaniser's love life proved as deadly as his day job.

One of his earliest victims was not a gangster, but a hotel boss who objected to his affair with a receptionist.

His hits for the mob were even darker.

In 1993, after executing rival boss Vincenzo Milazzo, he turned his attention to Milazzo's pregnant girlfriend and strangled her to death.

He is also believed to be involved in the abduction and murder of 11-year-old Giuseppe di Matteo.

10 An e-fit of Denaro from 2007. There are fears he may have had plastic surgery to evade cops Credit: AP:Associated Press

10 He is said to have kept tabs on Giovanni Falcone, a passionately anti-mafia judge whose was assassinated with a car bomb in 1992 Credit: ANSA/EPA

10 He then helped carry out the horrific Via Palestro massacre in 1993, part of a mafia bombing campaign that left 10 dead Credit: Alamy

10 Denaro was reportedly involved in the horrific murder of 11-year-old Giuseppe di Matteo Credit: .

10 The helpless child was kept captive for two years before being strangled to death

Denaro abducted him and held him captive for two years in a bid to stop his father testifying against the mafia.

The helpless child was eventually choked to death and disposed of in an acid bath.

When a bitter war erupted between the Cosa Nostra and state over stricter prison rules for convicted gangsters, Denaro emerged as one of its deadliest frontline soldiers.

First, he is said to have kept tabs on Giovanni Falcone, a passionately anti-mafia judge whose car was assassinated in 1992.

Alongside brutal hitman Giovanni Brusca – who boasted of single-handedly committing up to 200 murders – he helped to carry out a horrific bombing campaign across Florence, Milan and Rome.

Ten were killed and 93 injured during the attacks on some of Italy’s most historic monuments – and Denaro was forced into hiding.

Horrific aftermath of Via dei Georgofili bombing by Sicilian Mafia

Killer on the run

But life underground didn’t hinder Denaro’s rising prospects. After the reigning ‘boss of bosses’ Leoluca Bagarella was arrested in the aftermath of the bombings, new boss Bernardo Provenzano took the young prodigy under his wing, increasingly referring to him as his ‘nephew’.

Despite often being described as the ‘last Mohican of the old mafia’, particularly impressive was Denaro’s ability to bring the syndicate into the modern day.

Uniting the historically scattered clans around the city of Trapiani, he established fresh connections with the Columbia's rampant cocaine cartels.

What you hear all the time in town is how the mafia gives work and the government takes it away

Much like his counterpart Pablo Escobar, he envisioned himself as a folk hero to the city’s residents as business boomed.

"What you hear all the time in town, and on blogs, is how the mafia gives work and the government takes it away," Francesco Garofalo, a member of anti-mafia group Libera, told the Guardian.

"There are people here who would like to see Messina Denaro appointed mayor."

Among some of the Mafia’s oldest members, however, his rampant affairs – which saw him father a daughter in 1995 – raised eyebrows as a departure from the more traditional family values of decades past.

Avoiding phones or the Internet, Denaro communicated chiefly through handwritten notes known as 'pizzini', moving from house to house through a swelling network of loyal followers and adoring citizens.

When Provenzano’s 43 years on the run came to an end with his arrest in 2006, Denaro was widely tipped as his successor.

His death in 2016, followed that of influential godfather Toto Riina the next year, cemented his position at the very top of the Cosa Nostra.

The search for Matteo Messina Denaro and his £2.5bn fortune

10 The arrest of Bernado Provenzano in 2006 paved the way for Denaro to cement his position at the top of the mafia Credit: Reuters

10 He is believed to be hiding out near his hometown of Castelvetrano, in the province of Tapani in southern Italy Credit: Alamy

£2.5billion ghost

Hot on Denaro’s tail is an elite team of Mafia hunters called the Catturandi, who have snared some of Italy’s biggest crime bosses.

In 2017, the net tightened as 200 officers searched caverns and bunkers around Castelvetrano – believing he was living a Bin Laden-esque fugitive lifestyle below ground.

Yet with every manhunt, he remains a ghost. And the arrest of windfarm magnate Vito Nicastri, who has now been jailed for nine years, shows why.

Continuing to modernise the mob, Denaro’s expansion into alternative energy as a means of money laundering has proved invaluable – earning him an estimated £2.5billion personal fortune with which to bankroll his concealment.

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"They (the mafia) know they can't kill people as they used to,” a Catturundi agent told the BBC.

“So now the whole system has evolved into an intricate web of interests that entangles politics, finance and the very structure of Sicilian society.”

While the Cosa Nostra's influenced may have waned since its heyday 20 years ago, the hunt for its most infamous figurehead shows no sign of slowing down.

Whether it can ever catch up remains to be seen.

10 Denaro helped modernise the mob by strengthening ties with South America. Pictured, a haul from Italy's 'Ndrangeta mafia Credit: ANSA