Along with his brothers John, Vincent, Victor, and Michael, Tony became involved in criminal activity early in life. Another of Tony's brothers, Pasquale Spilotro, Jr., went on to college and became a highly respected oral surgeon in the Chicago area. Described as a bully at school, Tony dropped out of Chicago's Steinmetz High School in his sophomore year and quickly became known for a succession of petty crimes.
Bookmaker Frank "Lefty" Rosenthal was first linked to Spilotro in 1962, when Spilotro plead guilty to attempted bribery of a New York University basketball player in a game against West Virginia University. There is also suspicion that Spilotro tried to bribe a University of Oregon football player.
Spilotro became a marked man to local law enforcement. He was arrested numerous times for mopery, a vague and spurious criminal charge defined as "walking down the street with no clear destination or purpose." Spilotro befriended Vincent Inserro, who introduced him to Chicago Outfit higher ups, such as Joseph "Joey Doves" Aiuppa, Jimmy "The Turk" Torrello, Joseph "Joey The Clown" Lombardo and William "Willie Potatoes" Daddano, Sr., all of whom would eventually climb up the ranks of the Chicago mob. Spilotro joined the crew led by Sam "Mad Sam" DeStefano, and was also mentored by Felix "Milwaukee Phil" Alderisio and Charles "Chuckie" Nicoletti. Spilotro became a "Made Man" in 1963 and was assigned to a large bookmaking operation. For a while, Spilotro was a bail bondsman for reputed mob associate Irwin "Red" Weiner.
The FBI first "flipped" Charles "Chuckie" Crimaldi, a former associate of Sam DeStefano. Crimaldi had been a "juice collector" for DeStefano during the 1950s and 1960s. Crimaldi gave evidence against Spilotro and DeStefano in the murder of real estate agent-loan shark Leo Foreman on November 19, 1963. DeStefano and Spilotro were both acquitted. Crimaldi also provided information on his part in luring William "Action" Jackson to his death. Jackson was another loan shark and enforcer who worked for DeStefano and had been indicted on a hijacking charge. DeStefano suspected Jackson of cutting a deal with the FBI in exchange for a lighter sentence, after Jackson was allegedly spotted with agents in a Milwaukee restaurant owned by Louis Fazio, a DeStefano associate. FBI agent Roemer denied Jackson had cut any deal with the agency.
Later, Sal Romano, a member of the Hole in the Wall Gang that specialized in disabling alarm systems, became a government informant. Romano worked counter-surveillance during the July 4 burglary at Bertha's jewelry store in Las Vegas. Unbeknownst to Spilotro, his brother John, partner Herbie Blitzstein, and the Hole in the Wall Gang burglars, Romano had turned informant several months earlier; federal agents and police were waiting for the burglars when the heist at Bertha's went down.
Spilotro's boyhood friend, Frank Cullotta, admitted that for many years he'd done "muscle work" on Spilotro's behalf, including the 1962 "M&M Murders" of James Miraglia and Billy McCarthy[citation needed]. Spilotro had ordered the killings after the two men robbed and murdered three businessmen in a suburban Chicago neighborhood where several members of the Chicago Outfit lived, territory that was considered off limits.
After his own arrest, Cullotta subsequently became a federal witness, or a "snitch" to save himself, after he thought Spilotro was out to kill him. In November 1981, Cullotta was arrested for a previous burglary, in which a woman's home was broken into and her furniture stolen. The furniture was later found in Cullotta's home, which led to his indictment on possession of stolen property. Cullotta was also a suspect in the 1979 Las Vegas murder of a mob associate, Sherwin "Jerry" Lisner.
Authorities discovered that Spilotro had ordered Hole in the Wall Gang member Lawrence "Crazy Larry" Neumann, 53, of McHenry, Illinois, to murder Cullotta and fellow burglar, Wayne Matecki, 30, of Norridge, Illinois.
Cullotta, who has publicly admitted to being a killer himself, supplied information about the M&M murders. Neumann tried to post bail for Cullotta so he could murder both Cullotta and Matecki, but the police had Culotta's bail revoked to protect him. Cullotta received eight years on the stolen property charges. In September 1983, Spilotro was indicted in Las Vegas, Nevada on murder and racketeering charges based on Cullotta's testimony, but the charges didn't hold up.
Meanwhile, Spilotro was tried before Cook County Circuit Judge Thomas J. Maloney, in Chicago, for the Miraglia and McCarthy killings, while Cullotta's foiled executioner Neumann was sentenced to life in prison in 1983. Judge Maloney did not accept Cullotta's statements as evidence or as proof "beyond a reasonable doubt". The judge, in turn, acquitted Spilotro. (In 1992, Judge Maloney was convicted through Operation Greylord of accepting bribes in several unrelated cases, including murder cases.)
Cullotta testified before the President's Commission on Organized Crime, the Florida Governor's Commission on Organized Crime and appeared at a sentencing hearing for the Chicago mobster Joseph Lombardo. Cullotta later served as a technical advisor for the movie Casino, and also played a small role as Curly, one of Remo Gaggi (as Joe Aiuppa)'s hitmen
In 1971, Spilotro succeeded the mercurial Johnny Nevada as the Mob's representative in Las Vegas. Spilotro reunited with his boyhood friend Frank "Lefty" Rosenthal, who ran several Outfit-backed casinos, including the Stardust. Spilotro and Rosenthal worked together to embezzle profits from the casinos (i.e., "the skim"), which were then sent back to The Outfit and other Midwestern Mafia families, such as Kansas City, St. Louis and Milwaukee. On his own, Spilotro (under the alias Tony Stuart) took over the gift shop at the Circus-Circus Hotel, a "family" hotel on the Las Vegas Strip. The hotel offered first-class entertainment for children, while their parents gambled in the casino. Parts of the James Bond film Diamonds Are Forever were shot there. In 1971, the hotel was owned by Jay Sarno, who had purchased the property with a $43 million loan from the Teamster's Central States Pension Fund. In 1974, Circus-Circus was sold; for Spilotro's $70,000 investment, he received $700,000. In 1972, Spilotro was indicted in Chicago for the murder of Leo Foreman, a real estate agent/loan shark, who had made the mistake of throwing Sam DeStefano out of his office, in May 1963. Foreman was eventually lured to Sam's home to play cards. There, Foreman was tortured by repeatedly being stabbed with an ice pick and had pieces of his flesh cut out, before being shot and killed.
In 1976, Spilotro opened The Gold Rush, Ltd. with Chicago bookmaker Herbert "Fat Herbie" Blitzstein and brother Michael Spilotro. The Gold Rush, located one block from the Las Vegas Strip, was a combination jewelry store and electronics factory. Here Spilotro, brother John, and Blitzstein gained expertise in fencing stolen goods.
Where Rosenthal was responsible for the actual management of the casinos, Spilotro's primary task was to control casino employees and other personnel involved in the skim/embezzlement scheme. Spilotro's role as enforcer, however, was severely curtailed after he was blacklisted by the Nevada Gaming Commission, in December 1979, (then chaired by current United States Senate Majority Leader Harry Reid), a ruling that legally prevented him from being physically present in any Nevada casino. Spilotro was blacklisted as a direct result of court testimony of Aladena "Jimmy The Weasel" Fratianno, following his arrest, in 1977.
Spilotro, in 1976, formed a burglary ring with his brother Michael and Blitzstein, utilizing about eight associates as burglars. The crew became known as the Hole in the Wall Gang because of its penchant for gaining entry by drilling through the exterior walls and ceilings of the buildings they burgled. The Hole in the Wall Gang operated out of The Gold Rush, Ltd. Other gang members included Samuel Cusumano, Joseph Cusumano, Ernesto "Ernie" Davino, 34, Las Vegas, "Crazy Larry" Neumann, Matecki, Salvatore "Sonny" Romano, Leonardo "Leo" Guardino, 47, Las Vegas, Cullotta, 43, Las Vegas, and former Las Vegas detective, Joseph Blasko, 45, Las Vegas, who acted as a lookout and who later worked as a bouncer at the Crazy Horse Too, a gentleman's club, and died of a heart attack in 2002.
Following the botched burglary at Bertha's Household Products on July 4, 1981, Cullotta, Blasko, Guardino, Davino, Neumann, and Matecki were arrested and each charged with burglary, conspiracy to commit burglary, attempted grand larceny and possession of burglary tools. They were locked into the Las Vegas police department's holding cell in downtown Las Vegas. The only members of Spilotro's gang not arrested for the July 4 burglary was Blitzstein, Michael, and Cusumano.
By this time, Spilotro's relationship with Rosenthal had collapsed, as Tony had had an affair with Rosenthal's wife, Geraldine McGee Rosenthal. Meanwhile, Cullotta had turned state's witness, testifying against Spilotro. But the testimony was insufficient and Tony was acquitted.
Getting blacklisted from the very casinos he was supposed to be overseeing, generating unwanted media attention through his high-profile jewel heists, and breaking the Outfit's rules by sleeping with an associate's wife, proved to be a lethal combination for Tony Spilotro. After the accession of a new boss of the Chicago crime family, Joseph Ferriola, the decision was made to have Spilotro murdered. It is suspected that Tony and his brother Michael were called by Sam "Wings" Carlisi to a meeting at a hunting lodge owned by Spilotro's former mob boss, Joey Aiuppa. The Spilotros were savagely beaten and buried in a cornfield in Enos, Indiana. Tony and Michael were identified by their brother Pasqaule Jr. through dental records. In 2007, mob hit-man Nicholas Calabrese testified at the "Family Secrets" trial in Chicago that the brothers were killed in a Bensenville, Illinois, basement where the Spilotros believed that Michael would be inducted into The Outfit.
An autopsy performed on the recovered bodies found sand in the brothers' lungs, leading FBI examiners to conclude that they had been buried alive. No arrests were made until April 25, 2005, when 14 members of the Chicago Outfit (including reputed boss James Marcello) were indicted for 18 murders, including the Spilotros'. As a result of that investigation, the murders of the Spilotro brothers are now thought to have taken place in DuPage County, Illinois -- in Joey Aiuppa's hunting lodge, where they were beaten and strangled before being buried in a cornfield alongside Highway 41 in northwest Indiana. At the time of Spilotro's murder, Aiuppa was in prison, but Spilotro must have thought the building was still in use as a hunting lodge.
The suspected murderers included capo Albert Tocco from Chicago Heights Illinois, who was sentenced to 200 years after his wife Betty testified against him in 1989. She claimed that the day after the Spilotro murders, she was called to pick up Tocco 1.6 km (one mile) from where the brothers' bodies would later be found. She said that Tocco was dressed in dirty blue work clothes. Betty Tocco further implicated Nicholas "Nicky" Guzzino, Dominick "Tootsie" Palermo and Albert "Chickie" Rovero in the Spilotro brothers' murders. Tocco died at the age of 77 in an Indiana prison on September 21, 2005.
Another suspect in the murders was Frank "The German" Schweihs, an extortionist, convicted burglar and alleged Chicago assassin with two felony murder charges pending against him, while he is suspected of at least 73 others including the Spilotros, Allen Dorfman (of the Teamster's Pension Fund), and a former girlfriend. Schweihs was arrested by the FBI on December 22, 2005. At the time, Schweihs was a fugitive living in a Berea, Kentucky, apartment complex. Schweihs had slipped away before prosecutors were able to nail him and 13 others, including reputed Chicago mob boss James Marcello.
On May 18, 2007, the star witness in the government's case against 14 Chicago mob figures pleaded guilty to taking part in a conspiracy that included 18 murders, including hits on Anthony Spilotro and Spilotro's brother, Michael, in 1986.
Under heavy security, Nicholas Calabrese admitted that he took part in planning or carrying out 14 of the murders, including the Spilotro killings. The husky, white-haired Calabrese became the key witness against his brother, Frank Calabrese Sr., and other major mob figures charged in the government's Operation Family Secrets investigation. The investigation was aimed at clearing up old, unsolved gangland killings and bringing down Chicago's organized crime family.
Nicholas Calabrese reportedly agreed to testify after the FBI showed him DNA evidence to link him to the murder of fellow hit-man John Fecarotta, who was also allegedly involved in the Spilotro slayings. Frank Calabrese Sr.'s trial in Chicago's Everett M. Dirksen U.S. Courthouse began on June 19, 2007, and ended on September 10, 2007, with the conviction of Frank Calabrese Sr. and four other men associated with the Chicago mob: Joey "the Clown" Lombardo, James Marcello, Paul "the Indian" Schiro, and a former Chicago Police officer, Anthony "Twan" Doyle.
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