Messina Denaro used the pseudonym "Alessio" in his clandestine correspondence with former Mafia boss Provenzano. He suffers from severe myopia and received treatment for this condition at a clinic in Barcelona, Spain in 1994 and 1996.
Messina Denaro is often portrayed as a ruthless playboy mafioso and womaniser, driving an expensive Porsche sports car and wearing a Rolex Daytona watch, Ray Ban sunglasses and fancy clothes from Giorgio Armani and Versace. He is an ardent player of computer games, and is said to be the father of an illegitimate child, which is unusual in the conservative culture of the Mafia. Matteo has a reputation for fast living and allegedly killed a Sicilian hotel owner who accused him of taking young girls to bed. As such, he is remarkably different from traditional Mafia bosses like Salvatore Riina and Bernardo Provenzano who claim to adhere to conservative family values.
Matteo Messina Denaro was born into the Denaro Family (a well-known Mafia family) in Castelvetrano in the province of Trapani, Sicily. His father Francesco Messina Denaro, known as Don Ciccio, was the capo mandamento of Castelvetrano and the head of the Mafia Commission of the Trapani region. Matteo learned to use a gun at 14, and committed his first of many murders at 18. He is estimated to have killed at least 50 people. "I filled a cemetery all by myself," he once bragged. He made a reputation by murdering rival boss Vincenzo Milazzo from Alcamo and strangling Milazzo’s three-months pregnant girlfriend.
His father started as a campiere (armed guard) of the D’Alì family, wealthy landowners who were among the founders of the Banco Sicula. He became the fattore (overseer of an estate) of the D’Alì land holdings. They handed over a significant estate in the area Zangara (Castelvetrano) to Messina Denaro. However, the real new owner turned out to be Salvatore Riina, with whom Messina Denaro was allied.
Antonio D'Alì Sr. had to resign from the board of the Banco Sicula in 1983 because he appeared on the list of the secret freemason lodge Propaganda Due (P2) of Licio Gelli. His son Antonio D'Alì jr. became a senator for Silvio Berlusconi's Forza Italia party in 1996, and in April 2001 under-secretary at the Ministry of the Interior, the institution responsible for fighting organised crime. His cousin Giacomo D’Alì is a counsellor of the Banca Commerciale Italiana (Comit) in Milan, which acquired the Banca Sicula in 1991. Matteo’s brother Salvatore Messina Denaro, arrested in November 1998, worked at the Banca Sicula and continued to work for Comit.
After the natural death of his father in November 1998, Matteo became capo mandamento of the area including Castelvetrano and the neighbouring cities, while Vincenzo Virga ruled in the city of Trapani and its surroundings. After the arrest of Virga in 2001, Messina Denaro took over the leadership of the Mafia in the province of Trapani. He is said to command some 900 men and apparently reorganised the 20 Mafia families in Trapani into one single mandamento separated from the rest of Cosa Nostra. The Trapani Mafia is considered the zoccolo duro (solid pedestal) of Cosa Nostra and the most powerful except for the families in Palermo.
Messina Denaro gets his money through an extensive extortion racket forcing businesses to pay a pizzo (protection money) and skimming off public construction contracts (the family owns substantial sand quarries). He is also active in the international drug trade, allegedly with the Cuntrera-Caruana clan, attracting attention of the US Federal Bureau of Investigation (FBI).
According to the Direzione distrettuale antimafia (DDA) of Palermo, he maintains contacts with relatives in Western New York. He also has interests in Venezuela and contacts with Colombian drug trafficking cartels as well as the 'Ndrangheta. His illicit networks extend to Belgium and Germany.
Matteo Messina Denaro has strong links with Mafia families in Palermo, in particular in Brancaccio, territory of the Graviano Family. Filippo Guttadauro the brother of the Giuseppe Guttadauro – the regent of the Brancaccio Mafia while Giuseppe Graviano and Filippo Graviano are in jail – is the brother-in-law of Messina Denaro. They are involved in cocaine trafficking in agreement with ‘Ndrangheta clans from Platì, Marina di Gioiosa Ionica and Siderno, as well as the Mafia family of Mariano Agate.
After bomb attacks in Capaci and Via D'Amelio that killed prosecutors Giovanni Falcone and Paolo Borsellino, the arrest of Salvatore Riina on 15 January 1993 and the introduction of strict prison regime (article 41-bis), Cosa Nostra embarked on a terrorist campaign in which Matteo Messina Denaro played a prominent role.
The remaining Mafia bosses, among them Matteo Messina Denaro, Giovanni Brusca, Leoluca Bagarella, Antonino Gioè, Giuseppe Graviano and Gioacchino La Barbera, met several times (often in the Santa Flavia area in Bagheria on an estate owned by the mafioso Leonardo Greco). They decided on a strategy to force the Italian state to retreat. That resulted in a series of bomb attacks in the Via dei Georgofili in Florence, in Via Palestro in Milan, in the Piazza San Giovanni in Laterano and Via San Teodoro in Rome, which left 10 people dead and 93 injured as well as damage to centres of cultural heritage such as the Uffizi Gallery.
Messina Denaro also tailed the TV-journalist Maurizio Costanzo, host of the Maurizio Costanzo Show, who just escaped a car-bomb attack on 14 May 1993. Apparently he also observed the movements of Giovanni Falcone and the Minister of Justice, Claudio Martelli, in 1991. After the 1993 bombings Messina Denaro went into hiding and has not been seen since. On May 6, 2002, he received a life-time sentence (in absentia) for his role in the terrorist attacks of 1993.
In June 2000, a law enforcement operation led to the arrest of several individuals who assisted the fugitive Matteo Messina Denaro and discovered two residences where he had found shelter. One of these residences was located in an area of Bagheria, while the other was in the Brancaccio area of Palermo. Since one of the main rules within the Mafia is that a fugitive should hide in a friendly area, there is reason to believe that Messina Denaro has a good relationship to both Provenzano and the Gravianos.
Messina Denaro was one of the "young turks" within Cosa Nostra that wanted to set aside Bernardo Provenzano in 1998, according to the pentita Giusy Vitale. Next to Messina Denaro they were Giovanni Brusca, Domenico Raccuglia and Vito Vitale. The younger bosses wanted to take strategic decisions without prior consent of Provenzano. They told him to "go home and take care of your family."
After the arrest of Bernardo Provenzano on 11 April 2006, Matteo Messina Denaro is often mentioned as his successor. His main rivals are supposed to be Salvatore Lo Piccolo – boss of the mandamento of San Lorenzo in Palermo – and Mimmo Raccuglia from Altofonte. Allegedly Provenzano nominated Messina Denaro in one of his pizzini – small slips of paper used to communicate with other mafiosi to avoid phone conversations.
This presupposes that Provenzano has the power to nominate a successor, which is not unanimously accepted among Mafia observers. "The Mafia today is more of a federation and less of an authoritarian state," according to anti-Mafia prosecutor Antonio Ingroia of the Direzione distrettuale antimafia (DDA) of Palermo, referring to the previous period of authoritarian rule under Salvatore Riina. Provenzano "established a kind of directorate of about four to seven men who met very infrequently, only when necessary, when there were strategic decisions to make."
According to Ingroia "in an organization like the Mafia, a boss has to be one step above the others otherwise it all falls apart. It all depends on if he can manage consensus and if the others agree or rebel." Provenzano "guaranteed a measure of stability because he had the authority to quash internal disputes." According to Sergio Lari, deputy chief prosecutor of Palermo: "Either the directorate can choose a successor or we could again be in for a fiery time."
Ingroia said that it was unlikely that there would be an all-out war over who would fill Provenzano's shoes. "Right now I don't think that's probable," he said. Of the two possible successors, Ingroia thought Lo Piccolo was the more likely heir to the Mafia throne. "He's from Palermo and that's still the most powerful Mafia stronghold," Ingroia said.
After the arrest of Salvatore Lo Piccolo in November 2007, Messina Denaro is generally viewed as one of the possible leading Mafia bosses. According to Antonio Ingroia, one of the prosecutors of the Direzione Distrettuale Antimafia (DDA) of Palermo, the main leading figures in Cosa Nostra at the moment, Messina Denaro, Giovanni Riina, Domenico Raccuglia, Pietro Tagliavia and Gianni Nicchi, are still too young to be recognized as leading bosses of the organisation. The police believes that Messina Denaro is hiding out close to his family home at Castelvetrano, and is moving between safe houses. On 15 November 2009, Domenico Raccuglia was arrested in a small town near Trapani having been convicted in absentia for murder and other crimes, facing three life sentences.
On 18 November 2008, Italian authorities seized 700 million euros in assets from the supermarket king of Sicily, Giuseppe Grigoli, traceable to Messina Denaro. The assets include 12 businesses, 220 real estate holdings - including villas and apartment blocks - and 133 land holdings for a total of 60 hectares. Grigoli was arrested in December 2007 after authorities found documents linking him to Messina Denaro in the hideout where Provenzano was arrested in April 2006. Grigoli has the exclusive franchise for western Sicily of the SPAR supermarket chain.
"This is one of the most important operations in recent years," according to Palermo prosecutor Roberto Scarpinato. Investigators believe that through his supermarkets Grigoli was able to launder illicit profits for Cosa Nostra and give a legal cover to mafiosi. "Having conquered the food distribution market, Grigoli was able to give jobs to hundreds of people close to Cosa Nostra or recommended by the Mafia," Scarpinato said. From evidence discovered on tiny paper-scrap messages found in the hut where Provenzano was arrested, Messina Denaro "knew to the last comma the accounts of Grigoli's supermarkets", he added.
In January 2010, police seized construction companies, villas, shops and vehicles worth some 550 million euros from a western Sicilian construction magnate, Rosario Cascio, believed to be one of the main bankrollers and money launderers for Messina Denaro. Together with 700 million euros in assets taken from supermarket magnate Giuseppe Grigoli at the end of 2008 and 200 million euros from construction tycoon Francesco Pecora in November 2009. In total 1.4 billion euros have been seized, which is seen as a clear reminder of the deep-rooted economic power of Messina Denaro.
In September 2010, police seized a record amount of assets worth 1.5 bn euros from a Sicilian businessman Vito Nicastri accused of working with Messina Denaro. He had invested in wind and solar energy sources, as a way of laundering money. The Italian police is applying a new strategy to try to capture Messina Denaro, arresting scores of his underlings and seizing millions of euros in assets. "The circle is closing around the No.1 fugitive," Interior Minister Roberto Maroni said. Palermo Chief Prosecutor Francesco Messineo added that the aim of the strategy against Messina Denaro was to "dry up the water he swims in".
With the arrest of Gerlandino Messina, the alleged boss of Agrigento, on 23 October 2010 in Favara, Agrigento province, the circle around Messina Denaro tightens even more, as notes addressed specifically to Messina Denaro to discuss territorial division will provide clues to his whereabouts and recent activities.
On 15 March 2010, his brother Salvatore Messina Denaro was arrested along with 18 others in operation "Golem 2". They were part of a network surrounding the Mafia boss, and were charged with organising Messina Denaro's secret correspondence in order to help him remain on the run. Other charges include mafia association, corruption and protection rackets.
On 19 May 2011, an attempt to arrest Matteo Messina Denaro failed. Police surrounded a manor farm ten minutes from his hometown Castelvetrano. They were tipped by the secret service Agenzia Informazioni e Sicurezza Interna (Italian for "Internal Information and Security Agency" - Aisi), which had provided useful information for the previous arrests of Mafia bosses Giuseppe Falsone and Gerlandino Messina. However, there was no trace of Messina Denaro.
A new photofit of Messina Denaro was issued in March 2014 after an informant claimed to have seen him in hiding. Despite Denaro's known eye problems, the photofit was issued without glasses. He is described as slightly taller than previously known, and heavier, with hair still remarkably dark for his age. This came only months after Denaro's sister, Patrizia Messina Denaro, was arrested along with several other mafia associates in a serious blow to Denaro by Italian police.
In December 2014, there was mentioning of police coming close to apprehending Matteo Messina Denaro after Italian police made an estimated €20 million seizure of assets from him in the form of valuable olive groves in Trapani. Wiretaps had revealed Messina Denaro was receiving funding from the Fountain of Gold olive oil business based in the region.