Matteo Messina Denaro (; 26 April 1962 – 25 September 2023), also known as Diabolik (from the Italian comic book character), was an Italian mafia boss from Castelvetrano. He was considered to be one of the new leaders of the Cosa Nostra after the arrests of Bernardo Provenzano on 11 April 2006 and Salvatore Lo Piccolo in November 2007. The son of a Mafia boss, Denaro became known nationally on 12 April 2001 when the magazine L'Espresso put him on the cover with the headline: Ecco il nuovo capo della Mafia ("Here is the new Mafia boss").

Messina Denaro became a fugitive on the most wanted list of the Italian Ministry of the Interior in 1993; according to Forbes in 2010, he was one of the ten most wanted and powerful criminals in the world., Forbes Magazine, 13 May 2010Who is now on the World's Most Wanted list? The Guardian, 4 May 2011 With the deaths of Bernardo Provenzano in 2016 and Salvatore Riina in 2017, Messina Denaro was seen as the unchallenged boss of all bosses within the Mafia. After 30 years on the run, he was arrested on 16 January 2023 near a private clinic in Sicily's capital, Palermo, where he was reportedly undergoing chemotherapy under a false name. Messina Denaro died in a prison hospital on 25 September 2023 after falling into an irreversible coma at the age of 61, after receiving treatment for colon cancer.

Early life Matteo Messina Denaro was born in Castelvetrano in the province of Trapani, Sicily. His father, Francesco Messina Denaro, known as Don Ciccio, was the capo mandamento of Castelvetrano. Matteo learned to use a gun at 14. He once bragged: "I filled a cemetery all by myself." He made a reputation by murdering rival boss Vincenzo Milazzo from Alcamo and strangling Milazzo's three-month-pregnant girlfriend.

His father started as a campiere (armed guard) of the D'Alì family, wealthy landowners who were among the founders of the . He became the fattore (overseer of an estate) of the D'Alì land holdings. They handed over a significant estate in the area of Zangara (Castelvetrano) to Matteo Messina Denaro. However, the real new owner turned out to be Salvatore Riina, leader of the Corleonesi Mafia clan, with whom Messina Denaro was allied. Parlamento pulito. Il catalogo è questo , societacivile.it

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 was an ardent player of computer games, and is said to be the father of an extramarital child. Messina Denaro had a reputation for fast living and allegedly killed a Sicilian hotel owner who accused him of taking young girls to bed. Ecco il nuovo capo della mafia , L’Espresso, 12 April 2001 Cosa Nostra cerca il nuovo padrino , La Stampa, 13 April 2006 As such, he was remarkably different from traditional Mafia bosses like Salvatore Riina and Bernardo Provenzano who claimed to adhere to conservative family values.

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. Relazione conclusiva Final report of the Antimafia Commission, presided by senator Roberto Centaro, January 2006 He was said to reorganise 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.

According to the Direzione distrettuale antimafia (DDA) of Palermo, he had interests in Venezuela and contacts with Colombian drug trafficking cartels as well as the 'Ndrangheta. His illicit networks extend to Belgium and Germany. Il ruolo di Matteo Messina Denaro , La Sicilia, 18 April 2004

Messina Denaro had strong links with Mafia families in Palermo, in particular in Brancaccio, the territory of the Graviano Family. Filippo Guttadauro, the brother of 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. Attività di analisi, progettualità e strategia operativa , Direzione Investigativa Antimafia, 2° semestre 2003 Le indagini «Igres» , in the 2006 Final Report of the Italian Antimafia Commission

Fugitive after 1992/93 bombings

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 Messina Denaro played a prominent role.

The remaining Mafia bosses, among them Messina Denaro, Giovanni Brusca, Leoluca Bagarella, , 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. Ordinanza di custodia cautelare in carcere , Tribunale di Caltanissetta, Ufficio del giudice per le indagini preliminari, 11 April 1994

Messina Denaro also tailed the TV journalist Maurizio Costanzo, host of the Maurizio Costanzo Show, who had just escaped a car bomb attack on 14 May 1993. He also observed the movements of Falcone and the Minister of Justice, Claudio Martelli, in 1991. After the 1993 bombings, Messina Denaro went into hiding as of June 1993.

According to investigators, between 1994 and 1996 Messina Denaro spent time in his hiding place located between Aspra and Bagheria with his lover Maria Mesi, with whom he went on vacation to Greece under the false name of "Matteo Cracolici".Matteo Messina Denaro il "Re" di Trapani Antimafiaduemila.com

In 1995, Messina Denaro, who by then had a daughter from a previous relationship with Francesca Alagna, went to live with his mother. In a letter addressed to a friend, seized by investigators, Messina Denaro revealed that he had never met this daughter.

In 1999, Messina Denaro received his first life sentence, in absentia for the murder of Giuseppe Montalto, a prison guard at the Ucciardone prison in Palermo, killed in 1995.Testimonianze di coraggio, Giuseppe Montalto la guardia dell'Ucciardone uccisa per avvertimento

In 2000, Messina Denaro received a life sentence in absentia for the 1993 bomb attacks in Florence, Milan and Rome, and another life sentence later that year.

In 2000, Maria Mesi was arrested, and because police found love letters that she had exchanged with Messina Denaro, the following year she was sentenced to three years in prison for aiding and abetting together with her brother Francesco. In July 2006, investigators found other love letters from Maria Mesi at the home of Filippo Guttadauro, who had the task of delivering them to his brother-in-law Messina Denaro.

In 2003, Messina Denaro was given another life sentence in absentia, accused of hundreds of murders which occurred in the early 1990s during the Alcamo mafia feud fought between the Corleonesi and the Stiddaro clan of the Greco Mafia clan.

Possible successor of Provenzano According to Giusy Vitale, a pentita, in 1998, Messina Denaro was one of the young Turks within Cosa Nostra who wanted to set aside Bernardo Provenzano. In addition to Messina Denaro, they were Giovanni Brusca, Domenico Raccuglia, and Vito Vitale. The younger bosses wanted to make strategic decisions without the prior consent of Provenzano. They told him to "go home and take care of your family". "La nuova mafia era contro Provenzano", La Sicilia, 6 April 2005

After the arrest of Provenzano on 11 April 2006, Messina Denaro was often mentioned as his successor. His main rivals were supposed to be Salvatore Lo Piccolo, boss of the mandamento of San Lorenzo, Palermo, and Domenico Raccuglia from Altofonte. Provenzano allegedly nominated Messina Denaro in one of his pizzini, which are small slips of paper used to communicate with other mafiosi to avoid phone conversations. Mafia cerca il confronto con lo Stato , Sebastiano Gulisano, Polizia e democrazia, September 2001Prosecutors fear capture of mafia boss will spark bloody war of succession , by John Hooper, The Guardian, 13 April 2006 Messina Denaro used the pseudonym "Alessio" in his clandestine correspondence with former Mafia boss Provenzano. He suffered from severe myopia and received treatment for this condition at a clinic in Barcelona, Spain, in 1994 and 1996.Changes in Mafia Leadership Reveal New Links to US-Based La Cosa Nostra , DNI Open Source Center, 19 November 2007

This presupposed that Provenzano had the power to nominate a successor, which was not unanimously accepted among Mafia observers. According to anti-Mafia prosecutor Antonio Ingroia of the Direzione distrettuale antimafia (DDA) of Palermo, "The Mafia today is more of a federation and less of an authoritarian state", referring to the previous period of authoritarian rule under Salvatore Riina. Ingroia says that 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".The Mafia after Provenzano-peace or all-out war? , Reuters, 12 April 2006.

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 whether he can manage consensus and whether the others agree or rebel." For Ingroia, 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. He said: "Right now I don't think that's probable." Of the two possible successors, Ingroia thought Lo Piccolo was the more likely heir to the Mafia throne, saying: "He's from Palermo and that's still the most powerful Mafia stronghold."In Sicily, the end of 'Pax Mafiosa'? , International Herald Tribune, 13 April 2006

After the arrest of Lo Piccolo After the arrest of Salvatore Lo Piccolo in November 2007, Messina Denaro was generally viewed as one of the possible leading Mafia bosses. 'Vincere Cosa nostra? Arresti e lavoro'. Intervista al magistrato De Lucia , Ateneonline, 20 November 2007 According to Antonio Ingroia, one of the prosecutors of the Direzione distrettuale antimafia (DDA) of Palermo, the main leading figures in Cosa Nostra at that point, Messina Denaro, Giovanni Riina, Domenico Raccuglia, Pietro Tagliavia and Gianni Nicchi, were still too young to be recognized as leading bosses of the organisation. Lo Piccolo, il fautore della strategia della "rimmersione" , Intervista ad Antonio Ingroia, Antimafia Duemila n. 56, Anno VII° Numero 5 – 2007 The police believed that Messina Denaro was hiding out close to his family home at Castelvetrano and moved 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.Sicilian police arrest Mafia boss , BBC News, 15 November 2009