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Reputed by investigators to be one of the Italian Mafia’s most powerful bosses, Matteo Messina Denaro disappeared in the summer of 1993 and spent the next 30 years on the run as the state cracked down on the Sicilian mob.

From then on, he lived as a fugitive in western Sicily, his stronghold, eluding law enforcement thanks to the help of complicit townspeople – all while remaining at the top of Italy’s most-wanted list and increasingly becoming a figure of legend.

That was until eight months ago when, on January 16, 2023, his need for colon cancer treatment led to his capture. He was tracked down and arrested in hospital.

On Monday, having spent almost half his life on the run after being convicted of heinous crimes, and just eight months since he was finally arrested, he died aged 61.

One of the most ruthless bosses in Cosa Nostra, the real-life Sicilian crime syndicate depicted in the Godfather movies, Denaro’s capture was years in the making.

Reputed by investigators to be one of the Italian Mafia’s most powerful bosses, Matteo Messina Denaro (pictured left and right) disappeared in the summer of 1993 and spent the next 30 years on the run as the state cracked down on the Sicilian mob

Denaro lived as a fugitive in western Sicily, his stronghold, eluding law enforcement for 30 years thanks to the help of complicit townspeople – all while remaining at the top of Italy ‘s most-wanted list and increasingly becoming a figure of legend. That was until eight months ago when, on January 16, 2023, his need for colon cancer treatment led to his capture

Maria Mesi (pictured) reportedly had a relationship with Matteo Messina Denaro and helped him shelter in the 1990s

Patrizia Messina Denaro (pictured) was arrested by cops at her home in December 2013

The fourth of six children born to Francesco Messina Denaro, who controlled Sicily’s Trapani province for the Mafia, he was initiated at 14 and quickly earned a reputation for dispassionate violence against men, women and children.

When a local hotel manager tried to end his romance with an attractive Austrian receptionist – fearing guests would be deterred by the presence of a swaggering young mafiosi – he had the man murdered. 

And when a Cosa Nostra member was discovered to be a police informer, Denaro kidnapped the man’s 11-year-old son, holding the boy prisoner for two years before strangling him and dissolving his body in acid.

He used the same disposal method after having four mafiosos who opposed his father’s decisions summarily throttled, and it was likely used to get rid of a further 50 or more victims, killed by Denaro or on his orders.

He once boasted that he had ‘filled a cemetery all by myself’. 

Perhaps his most shocking act came in 1993, when he is reported to have assassinated rival boss Vincenzo Milazzo. His attention then turned to his victim’s pregnant girlfriend, who he lured to the murder scene on the pretext that Milazzo was waiting to see her, then strangled her to death.

As Denaro put his hands around her throat, she pleaded with him to spare her unborn child, yet he took two innocent lives without an ounce of pity.

The bodies were in the countryside.

As head of the Castelvetrano clan, Denaro was allied to the Corleonesi clan, who were immortalised in the legendary ‘The Godfather’ films.

He also became one of Cosa Nostra’s deadliest soldiers when a war erupted between the mafia and the state over stricter prison laws for convicted gangsters.

Such chilling dedication to the cause impressed Salvatore ‘Toto’ Riina, then godfather of the Sicilian Mafia. Denaro came to be regarded as his heir.

During the early 1990s, when Riina tried to bring the Italian government to heel with an all-out terror campaign, Denaro proved to be a willing assassin.

He was found to have had a hand in the killing of Giovanni Falcone, his wife, and three police escort officers, who died in a blast on May 23, 1992, as they crossed a bridge beneath which was planted 300kg of explosives.

Two months later, Denaro had a leading role in a second bomb attack which killed judge Paolo Borsellino, another judge who worked to rid Italy of organised crime.

In 2002, he was convicted in absentia for his involvement in the murder of the two judges in 1992, and in bomb attacks on historic monuments in Florence, Rome and Milan that killed 10 people and injured 93.

The attacks were carried out alongside notorious hitman Giovanni Brusca (who boasted of murdering 200 people single-handedly) and it was these attacks that forced him into hiding. 

Another of his six life sentences was for the kidnapping and subsequent murder of the 12-year-old son of a witness in the Falcone case.

His sentences were handed down as part of a maxi-trial against the Sicilian Mafia.

In 1993, Messina Denaro helped organise the kidnap of a 12-year-old boy, Giuseppe Di Matteo (pictured), in an attempt to blackmail his father into not giving evidence against the mafia, prosecutors say. The boy was eventually strangled, and his body dissolved in acid

Messina Denaro was sentenced in absentia to a life term for his role in 1992 in the murders of anti-mafia prosecutors Giovanni Falcone and Paolo Borsellino. Pictured: The scene of the murder of Falcone in Palermo, Sicily, in 1992 

The scene of the bomb attack which killed Judge Giovanni Falcone on 24 May 1992 in Palermo, Sicily

The mafia boss, who comes from the small town of Castelvetrano in Sicily, also faces a life sentence for his role in bomb attacks in Florence, Rome and Milan which killed ten people in 1993. The bombs targeted some of Italy’s most famous landmarks

However, the sentence and being forced underground did little to quell his influence in the outside world. 

His brutal criminal actions put him firmly at the top of Italy’s most wanted list, and on the FBI’s 10 Most Wanted list – where he would remain for almost three decades.

During that time, Denaro outsmarted Italy’s top mob-busters at every turn, savouring the hedonistic fruits of his multi-billion criminal empire – including a harem of beautiful women enlisted to ease his isolation.

Despite his fame and notoriety, authorities had just a few, grainy photos of him, taken when he was a young man, and his voice had been sketchily recorded only once – when he gave evidence at trial.

Investigators have since said their search for him was ‘like hunting a ghost.’

He never used phones or computers to deliver his orders, with police finding he would communicate with underlings by ‘pizzini’, small pieces of paper tightly wrapped in Sellotape so they could only be opened once before being burnt.

Unwitting messengers included an acolyte’s five-year-old daughter, recruited after he treated her to an ice cream.

At one point during the hunt for the elusive mob boss, authorities released e-fits of what Denaro might look like today, including a mock-up of his appearance were he wearing women’s clothing as a disguise.

But despite pleas to the public by authorities, Denaro remained hidden, and during this time, he rose higher in the ranks of the Sicilian mafia.

After ‘boss of bosses’ Leoluca Bagarella was arrested in the clampdown that followed the bombing spree, Messina Denaro was taken under the wing of Bernardo Provenzano who would increasingly refer to him as his ‘nephew’. 

From there, Denaro worked to bring the mafia into the modern age.

He united the scattered mafia clan’s around the city of Trapiani, formed connections with South America’s cocaine cartels, and cultivated a Robin-hood like status. 

At the same time, he had numerous sources of revenue, from drug trafficking to gambling, both in Italy and abroad. 

Despite his fame and notoriety, authorities had just a few, grainy photos of him, taken when he was a young man, and his voice had been sketchily recorded only once – when he gave evidence at trial

Messina Denaro, captured in January after three decades on the run, died on Monday in hospital in central Italy. The 61-year-old had been treated for colon cancer

But despite his reputation as a moderniser, he had to avoid using phones and the Internet to reduce his chances of being caught.

His womanising ways also raised eyebrows among the clans more conservative members. He fathered a daughter in 1995 out of wedlock, which was seen as not being in keeping with Cosa Nostra’s more traditional family ‘values’.

Nevertheless, he climbed to the top. When Provenzano was arrested in 2006 after decades on the run, Messina Denaro was tipped as his obvious successor.

And with his mentor’s death in 2016 – followed by the death of influential godfather Toto Riina a year later – Messina Denaro was all but unopposed at pinnacle of the Sicilian Mafia, and was a popular figure among some of the locals.

The hunt intensified following Toto Riina’s death in 2017, but his pursuers received scant help from the locals in his province, who were either too terrified to volunteer information or revered him as a modern-day Robin Hood.

Yet unlike his predecessors, who spread their wealth among the poor to curry loyalty, Denaro lavished his fortune on luxuries such as works of art, fine dining, incognito foreign travel and perhaps his only weakness – beautiful women. 

The ‘Last Godfather’, an avowed atheist who never married and had a string of lovers – at least one of whom bore him a child – was very much a playboy. When arrested, he was wearing a £35,000 Muller watch and a designer leather jacket.

And though his two known lairs in Campobello were unprepossessing side-street apartments, police who searched them found Viagra pills, condoms and expensive jewellery. A huge poster of Marlon Brando in his film role as The Godfather was displayed in the ground floor flat, a testimony to his ego.

Denaro’s secret bunker was found concealed in a closet full of clothes.

Police have found evidence he was spending £10,000 a week on luxury items.

Indeed, according to Carlo Pulici, a former financial police officer who spent many years attempting to trace him, Denaro’s insatiable lust almost proved his downfall. 

Through an informant, Pulici discovered – too late – that The Godfather was sheltering in a seaside villa in Bagheria, 20 minutes’ drive from Palermo. 

Carabinieri forensics officers are seen taking notes in front of the house of Italy’s top wanted mafia boss Matteo Messina Denaro in Palermo, January 17

Carabinieri police stand guard near the hideout of Matteo Messina Denaro, Italy’s most wanted mafia boss, after he was arrested, in the Sicilian town of Campobello di Mazara, January 17

Italian newspapers with the news of fugitive Matteo Messina Denaro’s arrest on January 17, 2023 in Bari, Italy

A woman displays a photograph that became iconic in Italy and shows top anti-mafia prosecutors Giovanni Falcone, left, and Paolo Borsellino, during a demonstration in the streets of Palermo, Sicily, Italy, Monday, Jan. 16, 레비트라처방 2023. The pair were killed Denaro and accomplices 

Pictured: Police reconstructions of the face of Messina Denaro shared to the public, depicting what he could look like today as an older man, and in costume as a woman

‘There were always lots of women going back and forth. Young, good-looking, high-class, because he was very generous to his lovers,’ he told the Daily Mail in January.

‘They weren’t only brought to him for sex. He would have relationships with them. He saw himself as a romantic. A Latin lover,’ he said.

‘Another lead I followed, in 2014, took me to Bologna. Denaro’s cousin owned a jewellery shop and when a diamond ring worth 30,000 euros disappeared from the shelves we deduced that the Mafia boss had it, because he was one of the few locals who could afford it.

‘He had fallen for a schoolteacher in Bologna – she was in her 30s, beautiful, tall and blonde – and he’d bought the ring for her. We followed her for a while, but we could never catch him with her.’

Finally, however, detectives caught wind of a solid lead.

By intercepting the phone calls of one of his sisters, investigators discovered that Denaro, now 60, had cancer. 

They believed he was being treated at the Maddalena clinic, using an alias, and the opportunity to bring him to justice for dozens of murders had finally arrived. 

Yet it could all end disastrously. He might have been tipped off, as had happened many times before, and fail to show up for his 9.15am chemotherapy appointment.

They could have been wrong in deducing that he was the polite, well-heeled patient who presented himself as landowner Andrea Bonafede, posed for selfies with his nurses and gifted them ‘home-grown’ olive oil.

And if they did have the right man, a gun battle might erupt in the clinic, given that Denaro had a penchant for violence, even by Mafia standards.

Before he was approached, around 100 officers, some armed with Beretta machine guns, surrounded and sealed off the building.

Investigators gathered around screens receiving live images from drones hovering above the hospital in the suburbs of Palermo. Others whispered prayers and drew crucifixes across their navy blue jackets.

Yet the show of force proved unnecessary.

Pounced on while making his way to the coffee bar, Denaro meekly surrendered and immediately volunteered his real name.

‘This is actually quite common for Mafia of a certain level,’ Palermo’s anti-crime commander Lieutenant Colonel Antonello Parasiliti Molica told Daily Mail at the time.

‘It is about protocol — a kind of code. They usually don’t run or show any emotion. They don’t react violently. Instead, they often compliment the arresting officers, and he did that. Before we put him on a helicopter and flew him to jail, he asked for a piece of paper and wrote down a message, congratulating the ROS and GIS [the two Italian special forces units that captured him] for treating him with humanity.’

As it became clear the mission had succeeded, the control room was filled with emotion. Lt Cl Parasiliti, who helped to plan the arrest and was among those watching the feed, said he and his colleagues cheered and hugged one another. 

Some wept unashamedly, among them a burly senior officer who has hunted Denaro for 25 years. ‘It was a cry of relief and of liberation,’ the man, who asked not to be named because of his sensitive work, said at the time.

‘You must understand that Messina Denaro had seemed unreachable,’ the Lieutenant Colonel said. ‘It was a symbol who fell.’

Carabinieri chiefs dedicated the arrest to a colleague who fell to his death while erecting a listening post aerial on a mountain, hoping to intercept Mafia calls.

A member of staff at the hospital, who asked to remain anonymous, told local media at the time: ‘He’d been coming here on and off for about a year. He’d had an operation a few months ago and was back for more tests and chemotherapy.

‘When I turned up for work this morning at 6am it was all quiet and then he arrived to do his Covid test. A few minutes later a police officer wearing full body armour as if he was going to war came in and said he was looking for a patient.

‘He said to remain calm and that armed officers were on every floor of the clinic. We had no idea who he was or what his background was.

‘The guy actually managed to get out and ran into a local bar but they tracked him down and that’s when all hell broke loose.’

As news of his arrest spread across Palermo, local residents had emerged to applaud and shake the hands of the Italian paramilitary police officers involved in the operation.

The residents were seen cheering and wiping away tears as they felt a wave of relief that Denaro, who had coordinated years of terror in Italy, had finally been detained.

Italian newspapers with the news of fugitive Denaro’s arrest on January 17, 2023

Whatever hopes existed that Denaro would serve his prison sentence – or cooperate with authorities – were short lived, however.

Prosecutors had hoped in vain he would collaborate with them and reveal Cosa Nostra secrets. But according to Italian media reports, Messina Denaro made clear he wouldn’t talk immediately after capture.

When he died, ‘he took with him his secrets’ about Cosa Nostra, state radio said.

After his arrest, Messina Denaro began serving multiple life sentences in a top-security prison in L’Aquila, a city in Italy’s central Apennine mountain area, where he continued to receive chemotherapy for colon cancer.

But in the last several weeks, after undergoing two surgeries and with his condition worsening, he was transferred to the prison ward of the hospital where he died.

His death ‘puts the end to a story of violence and blood’ L’Aquila mayor Pierluigi Biondi said as he confirmed the mobster’s death ‘following a worsening of his illness.’ It also means he takes the secrets of his brutal reign to the grave.

‘No-one should be denied prayers. But I cannot say I’m sorry,’ Deputy Prime Minister Matteo Salvini said of the mobster’s death.