Stefano Magaddino was one of the most feared figures in the American underworld, a man whose name became synonymous with the brutal rise of organized crime in Buffalo, New York. Known as “The Undertaker,” a nickname derived from his legitimate funeral home business, he built an empire that lasted decades and made him the longest-serving boss in American Mafia history. Born on October 10, 1891, in Castellammare del Golfo, Sicily, Magaddino was part of a powerful clan that included his cousin, the future New York crime boss Joseph Bonanno. According to FBI records, he arrived in the United States aboard the SS San Giorgio on February 7, 1909, settling in Brooklyn among a large community of fellow Castellammarese immigrants.

In New York, Magaddino became a leader of the group known as the “Good Killers,” and his primary rivals were the Buccellato family, who were also well established in Brooklyn at the time. In August 1921, he was arrested on suspicion of ordering the murder of Camillo Caizzo, a fellow gangster whose body was found in Newark Bay. The hired killer was a barber named Bartolo Fontana, who confessed to the crime and claimed Magaddino had forced him to do it. The murder was tied to a long-running feud, with Magaddino’s men believing the Buccellato family was responsible for the unsolved 1916 killing of his brother, Pietro.
Fontana, however, was actually a close friend of Caizzo, and his arrest set off a chain of separate events. Fontana lured Magaddino into a trap, calling him to say police were following him and he needed money. Magaddino took the bait and met Fontana at Grand Central Station, where detectives immediately surrounded him. He resisted but was subdued by a blow to the head, and was held in jail for 30 days before being released for lack of evidence.
After his release, Magaddino and his associate Jasper Milella were shot at while leaving a store, with two innocent bystanders killed in the crossfire. Shortly afterward, several Buccellato men were killed, and one informant later claimed Magaddino was responsible for the murders of Salvatore, Joseph, and Felice Buccellato in the 1920s. Realizing Brooklyn had become too dangerous, Magaddino moved to Buffalo while Milella relocated to Detroit, where he was gunned down on May 31, 1930. Magaddino’s path to power in Buffalo began through a series of leadership changes in the local Mafia.
In 1908, Giuseppe Di Carlo was granted permission to lead the Buffalo organization, but after his death in 1922, his son was considered too young to succeed him. Angelo Palmeri was appointed boss instead, but he quickly handed power over to Magaddino. The following year, Magaddino brought his brother Antonino to Buffalo from Sicily. During the 1920s, Magaddino’s criminal family became one of the most profitable in the country, focused heavily on loan sharking, extortion, gambling, and bootlegging.
Buffalo and Niagara Falls became major illegal gateways for alcohol coming from Canada during Prohibition. Italian immigrants were not only forced to buy smuggled liquor from Magaddino but also pressured into purchasing “homemade juice,” a non-alcoholic mixture sold door to door. Refusing to buy could have dangerous consequences. Magaddino also ran a legitimate funeral business, the Magaddino Memorial Chapel in Niagara Falls, which is said to have inspired his nickname, “The Undertaker.
” His second-in-command, John Montana, was a prominent businessman and political figure in the city who helped secure the family’s connections with local government. On May 19, 1936, a bomb intended for Magaddino exploded at the home of his sister and brother-in-law on Whitney Street in Niagara Falls. His sister, Arcangela Longo, was killed and her three young daughters were injured. The killers had targeted the wrong house; Stefano and his sister were neighbors.
During the late 1920s and early 1930s, the Castellammarese War raged in New York between the factions of Salvatore Maranzano and Joe Masseria. Magaddino aligned with Maranzano, while Charles “Lucky” Luciano and Vito Genovese backed Masseria. In a fateful turn, Luciano and Genovese secretly contacted Maranzano and agreed to betray Masseria in exchange for an end to the conflict. On April 15, 1931, Masseria was murdered at a restaurant in Coney Island, ending the war.
Maranzano reorganized the New York Mafia into five families and declared himself “capo di tutti capi,” or boss of all bosses. His reign was short-lived; he was killed in his Manhattan office later that year by Jewish hitmen recruited by Meyer Lansky. In 1931, Luciano formed “The Commission,” a governing body designed to oversee Mafia activity across the country and mediate disputes between families, effectively abolishing the position of “boss of all bosses. ” Magaddino was chosen as one of the seven original members.
In 1940, the U. S. Treasury Department reported receiving information that Magaddino was a member of the high council of the Sicilian underworld in the United States. They also noted that between 1916 and 1921, he had been involved in at least three murders and should be considered armed and dangerous.
The most significant event of Magaddino’s career came in 1957, when he helped organize the infamous Apalachin Meeting. After the murder of Albert Anastasia and the rise of Vito Genovese in New York, Genovese sought to legitimize his power by calling a national meeting of Cosa Nostra leaders. He enlisted Magaddino to plan it, and Magaddino chose Joseph Barbara and Russell Bufalino to handle the arrangements. The meeting was held at Barbara’s estate in Apalachin, New York, to divide Anastasia’s criminal enterprises and discuss loan sharking, drug trafficking, and gambling.
For over a year, New York State Trooper Edgar D. Croswell had been watching Barbara, a wealthy businessman who owned a nearby Canada Dry bottling plant. Croswell became suspicious after a guest at Barbara’s home was stopped for speeding and presented a false ID; the driver turned out to be the notorious Carmine Galante. Croswell also discovered that Barbara’s son had been booking hotel rooms in the area and that a local butcher was sending large amounts of meat to Barbara’s home.
Police set up a roadblock on November 14, 1957, just as the meeting was about to begin. Attendees quickly realized what was happening and began to scatter. Some fled through fields and woods but were captured, while others tried to escape by car but were stopped at the roadblock. Many mobsters, including Carlo Gambino, Joe Profaci, and Paul Castellano, claimed they had come to wish Barbara a speedy recovery from illness.
John Montana, who had until then been known as an honest Buffalo businessman, said he had car trouble and stopped at Barbara’s house to look for a mechanic. When the crowd began to scatter, he claimed he went for a walk in the woods before being arrested. Joe Bonanno, in his autobiography, claimed he was in the area to discuss business with his cousin Magaddino and that two of his men had accidentally wandered onto Barbara’s property while hunting. Making matters worse, one of his men was carrying his driver’s license, and because he had no identification of his own, authorities mistook him for Bonanno himself.
An informant later reported that Magaddino was indeed present at the meeting and that 12 prominent figures hidden in a secret room in Barbara’s house were never identified by police. The Apalachin Meeting was a major embarrassment for the FBI, and J. Edgar Hoover, who had long denied the existence of the Mafia, was forced to respond. The FBI began using illegal “black bag” wiretaps to listen to mob conversations.
Agents heard Sam Giancana berating Magaddino by phone for helping organize the meeting. Though the illegal surveillance was not admissible in court, agents leaked some of it to the press seven years later. In the same year as the Apalachin meeting, a hand grenade was thrown through Magaddino’s kitchen window but failed to explode. In October 1960, two smugglers arrested while receiving a shipment of heroin turned informants, leading to indictments against Sicilian Mafia brothers Vito and Alberto Agueci, John Papalia, and 20 others.
Alberto Agueci paid tribute to Magaddino from his heroin trafficking profits while in prison, expecting Magaddino to pay his bail. When Magaddino did not, Agueci became enraged and threatened to become an informant, which could have exposed Magaddino’s involvement in drug trafficking to the Commission. Alberto managed to post bail by selling his home and borrowing money from a friend. On October 8, 1961, he left his family in Toronto to attend a court hearing in New York, but his charred body was found in a cornfield near Rochester, New York, on November 23, 1961.
An investigation revealed he had been tortured for days: several teeth were missing, ribs broken, skull shattered, genitals removed, and he had been bound with barbed wire, strangled, and burned. No charges were ever filed, but Magaddino is believed to have ordered the murder because of Agueci’s instability. The Magaddino Memorial Chapel, which served as Magaddino’s main gathering point, was later bugged by the FBI. Within just three years, the devices collected enough data to fill 70,000 pages of transcripts.
In 1963, Bonanno plotted to kill several of his rivals on the Commission, including Tommy Lucchese, Carlo Gambino, Magaddino, and Frank DeSimone. Bonanno enlisted Joseph Magliocco, head of the Profaci crime family, who agreed to support the plot. Magliocco ordered Joseph Colombo, one of his top hitmen, to assassinate Lucchese and Gambino, but Colombo instead reported the plan to the intended targets. Bonanno was ordered to appear before the Commission to explain himself but fled to Montreal instead.
While in Montreal, Bonanno was confronted by Vincenzo Cotroni, the Bonanno family boss there, who faced the impossible choice of serving his boss or the Commission. Buffalo’s mob threatened Cotroni with death because Magaddino believed Bonanno’s presence in Montreal signaled a desire to invade his territory in southern Ontario. Cotroni was forced to distance himself from Bonanno to survive. Bonanno was deported from Canada in the summer of 1964, and after returning to Manhattan, he was allegedly kidnapped by members of the Magaddino crime family on October 20, 1964, the day before he was due to appear before a grand jury.
He was released unharmed after six weeks. After 1967, Magaddino’s empire began to crumble. His top enforcer, Federico Randaccio, was arrested along with others on charges of associating with known criminals. Federal conspiracy charges followed regarding planned robberies, and informant testimony helped convict all defendants, resulting in 20-year federal sentences for Randaccio and Nicodemo Narducci.
Magaddino then began claiming poverty to his remaining underlings, demanding larger profit shares and withdrawing incentives he had previously granted. The following year, Magaddino and his son Peter were detained in connection with a sports betting investigation. Nearly $500,000 in cash was found during a search of Peter’s home and the Magaddino Memorial Chapel. This eventually led to a rebel faction choosing Sam Pieri as acting boss, Joseph Fino as acting underboss, and Joseph Di Carlo as acting consigliere in July 1969.
When the rebels demanded Magaddino step down, their request was denied, and the Commission refused to punish its aging member. Stefano Magaddino died of a heart attack on July 19, 1974, at the age of 82. For 50 years, he had played a dominant role in the Buffalo underworld, leaving a legacy that made him the longest-serving boss in American Mafia history.