Matteo Messina Denaro, a convicted killer and high-ranking mobster with the Sicilian Cosa Nostra who had eluded capture for three decades, died on Monday in a hospital in the central Italian city of L’Aquila, where he had been serving time in a maximum-security prison. He was 61.
Alessandro Cerella, an attorney for Mr. Messina Denaro, confirmed the death, which he said was from colon cancer. Mr. Messina Denaro had been undergoing treatment for several years, and on Friday he fell into a coma that doctors said was irreversible.
Mr. Messina Denaro was arrested in January while waiting to undergo chemotherapy at a private clinic in Palermo. He had been using a fake identity, and investigators discovered that he was being treated for cancer when they found a scrap of paper with his medical history rolled up in the leg of a chair in his mother’s home in Castelvetrano, Sicily.
Since he was not treated under his real name, they used national health service records to identify patients with similar conditions and narrow it down.
Despite operating in the shadows, Mr. Messina Denaro had remained at the top of Italy’s list of most wanted fugitives for decades. His ability to confound investigators on a dogged, if frustrating, mission to find him added to his aura of invincibility.
“La Cattura” (“The Capture”), a recently published book about hunting him down written by Maurizio de Lucia, the chief prosecutor in Palermo, calls Mr. Messina Denaro “one of Italy’s greatest mysteries.” He was, Mr. de Lucia wrote, “the mobster who ferried Sicily’s Cosa Nostra into a new era, within a criminal system that unites many segments.”
In 2020, Mr. Messina Denaro was convicted in absentia for his role in the high-profile murders of two of Italy’s top anti-Mafia prosecutors, Giovanni Falcone and Paolo Borsellino, in 1992, and for deadly bombings the next year in Milan, Rome and Florence that prosecutors believe were part of a Cosa Nostra strategy against the state.
He also received a life sentence for his involvement in the kidnapping and death of the 12-year-old son of a Mafia turncoat after the boy was strangled and his body was dissolved in acid, and in the death of a police officer.
Lirio Abbate, an investigative journalist, has also written a book about Mr. Messina Denaro. In that book, “U Siccu,” published 2020, Mr. Abbate said that Mr. Messina Denaro had confided in a friend that he could make “a cemetery” out of all the people he had killed or ordered killed.
What little is known about Mr. Messina Denaro comes by way of the testimony of Mafia turncoats and arrested mobsters, as well as court records, police reports and hearsay. Before his arrest, investigators had little to go on: a 1988 recording of his testimony about a murder and a handful of photographs of him as a young man.
Nicknamed U Siccu (Sicilian for slim), Mr. Messina Denaro was said to have had a penchant for fast luxury cars that he could not indulge in for fear of being caught. According to one investigator, he was wearing a watch valued at over 30,000 euros (about $32,000) when he was arrested. The police also found designer clothes and expensive perfumes in his last hide-out, an apartment in southwestern Sicily where Mr. Messina Denaro had been living for several years under an assumed name.
He told the investigators who caught him that in recent years he had lived largely in the open, “a tree in the midst of a forest,” thinking that he would be less likely to be caught. If anyone knew that he was a Italy’s most wanted mob boss, they had not said a word to the authorities.
He was said to be a “fimminaru,” or playboy, and books and articles about him recounted his conquests in Italy and abroad. Some women paid a high price, landing in prison for abetting his life as a fugitive. Mr. Abbate noted in his book that Mr. Messina Denaro’s philandering had broken with the “family values of the traditional Mafia.”
He is thought to have traveled extensively during his years on the run, establishing connections with criminal groups in Europe and the Americas. “He was everywhere and nowhere,” Attilio Bolzoni, a seasoned Mafia reporter, wrote after the arrest. “A ghost.”
Mr. Messina Denaro had taken his place at the Cosa Nostra table when his father, who also had Mafia affiliations, became a fugitive after his own legal troubles. In 1991, the son attended an infamous meeting at which prosecutors believe the Sicilian Mafia families decided to wage war against the central government by pulling off the high-profile assassinations and bombings of the early 1990s.
His rise within the echelons of organized crime was facilitated by his affiliation with the Corleonesi crime family, which was headed by Salvatore (Toto) Riina, the so-called Boss of all Bosses, who is said to have considered him like a son.
When a Mafia turncoat connected Mr. Messina Denaro to several murders in 1993, he went underground. But he maintained a firm hold over his turf, the western Sicilian province of Trapani, where he acquired assets in legal businesses including travel agencies, supermarkets and alternative-energy companies.
He communicated with associates through letters and handwritten messages that he avoided writing personally and demanded be burned once read. He was protected, experts said, by a large network of associates who feared and respected him, as well as locals who looked the other way.
Hundreds of people who helped him elude capture or benefited from his financial dealings were jailed over the years, including friends, family members and top business associates. Nearly 10 billion euros of his in assets and shares in various companies and businesses that were seized over the years were just “the tip of the iceberg,” according to Mr. de Lucia.
Piero Grasso, a onetime national anti-Mafia prosecutor, said that Mr. Messina Denaro was “much loved, because he was considered a benefactor in his territories” — a dynamic that helps explain why he was able to stay under cover for so long.
By the time he was arrested, he had accrued several life sentences. His final months were spent in jail, in court and receiving treatment for cancer. He had been scheduled to attend a hearing for one trial this month.
Mr. Messina Denaro was born on April 26, 1962, in Castelvetrano, a rural town in western Sicily, the fourth of six children. His father, Francesco Messina Denaro, known as “don Ciccio,” was a local crime family boss who died in 1998 while a fugitive. His mother, Lorenza Santangelo, was a homemaker.
He grew up on an estate belonging to a wealthy local family and attended a technical school in the area but did not finish high school, according to Mr. de Lucia’s book.
Information on survivors was not immediately available.
Mr. de Lucia wrote that during the interrogations after his arrest, Mr. Messina Denaro had continued to deny being part of the Mafia or participating in its killings.
Yet his violent streak began early.
“He was already shooting at 14,” Mr. Abbate wrote. “Killing at 18. At 31, he was placing bombs in the north. This is what we know about him, a boy with undeniable criminal skills.”
Mr. Messina Denaro maintained his innocence until the end, however; in one interrogation in February, he described himself as a “stateless farmer.” “I used to work in the countryside,” he said, complaining that he had lost his residence and his property. “I had assets, but you took them all away.”