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Aiuppa Joseph


Aiuppa Joseph: John AKA Doves Joey O’Brien Born December 1, 1907 Died February 22, 1997.  An amateur boxer who fought his way out of Chicago's Maxwell Street ghetto. Auippa started with the outfit under Frank Nitti in the 1930s, although he may have been a fringe player even before that, since Aiuppa claimed repeatedly that he was a hired gun for the Capone organization and acted as one of Capone’s many bodyguards and then moved into protection for Capone’s bootlegging, gambling and prostitution rackets. He had one arrest in all that time, for suspicion of robbery in 1935.

 Aiuppa rose through the ranks to become boss of Cicero bookies, and was later brought in to run one of the mob's biggest gambling joints and night clubs in Cicero, the 4811 Club. He was jailed in 1952 for his complete lack of cooperation the U.S. Senate's Kefauver Committee investigating organizing crime.

The committee sentenced him to six months in jail and fined $1,000 for refusing to answer questions put to him by the committee. In 1957, he was jailed for a year when he and a business partner failed to register with the government as dealers in gambling devices.    In 1976, Aiuppa, then 69-years-old made the top of the Chicago Crime Commission’s chart as the boss of Chicago's Mob. Aiuppa, a widower with no children, he lived alone on a five-acre suburban lot. By then he was an avid hunter who made yearly trips to the Canadian backwoods to pursue his hobby.  

He picked up the nick name "Joey Doves" (It was largely used only in the press) after he was arrested transporting mourning doves unlawfully across state lines on October. 2, 1962. Wild life agents found the fowl, 563 of them, dressed and stuffed in the gangster’s freezer. Aiuppa was proud of the fact that he and several of his men had killed the doves during a Kansas hunting trip by using shotguns and automatic revolvers to shoot the birds off of power lines. Aiuppa was later convicted of illegal possession and transportation of the doves and sentenced to three months in jail. The conviction was overturned by the U.S. Court of Appeals.  By 1971 Aiuppa was a power in the mob and is widely considered to have ordered the deaths of both Sam Giancana in June of 1975 and Tony Spilotro in 1986. Auippa is thought to have ordered the murder of Boss Sam Giancana in June of 1975 in retaliation to Giancana's refusal to grant Aiuppa and Accardo a percentage of the proceeds from an illegal gambling ship operation in Mexico.

 It is more likely that Giancana was killed because he had made remarks about not serving another day in jail, or what the bosses thought sounded like Giancana’s willingness to flip to the Governments side.   In June of 1985, Aiuppa and 40 gangsters were subpoenaed to testify before the President's Commission on Organized Crime which was looking into the Chicago Outfits massive gambling operations which was estimated to be about $40 million a month in wagers, most of it from sporting and horse racing events.

 In 1986, Auippa, his underboss Jackie Cerone and several other mobsters from Chicago and Kansas City were indicted for skimming millions from the Las Vegas casinos. As soon as the indictments were released, street taxes paid by bookmakers, gambling houses burglars and robbers to operate in the Chicago area and Las Vegas were increased from 15 to 25% to make up for the loss of income to the Chicago Outfit by the Las Vegas losses. Mob's extortionists raised the "fear fees," or money paid for protection, and loan sharks were levied with a surtax of sorts by the Outfit. Not everyone abided by the increase as the violent deaths of Chuckie English, Lenny Yaras and Hal C. Smith, within five weeks, showed.  

On January 10 1985, Lenny Yaras, the son of legendary hoodlum Dave Yaras was murdered as he made his usual rounds collecting street tax from bookies in the Rogers Park neighborhood, the same area his father had worked in fifty years before.  It came out later that although Lenny Yaras was known principally as a street tax collector from bookmakers and other gambling operators in Rogers Park and in the northern suburbs, he may also have been active in the narcotics trade, with or without the mobs permission. His father was considered a major narcotics importer in the late 1940s. 

 Yaras pulled his car up to 4224 West Division Street and stepped into A-1 Industrial Uniforms Company, which was actually a large laundry shop. Yaras claimed his mainline of work was a consultant to A-1 Industrial Uniforms.  He came back out at 10 a.m. and entered his late-model Oldsmobile on the north side of Division Street. As soon as he shut the door, a tan Chevrolet swung in front of his auto, preventing it from going forward. Two men wearing ski masks got out, and one opened the driver's side door of Yaras' car. The men shot Yaras four times in the face and once in the throat.

Yaras fell toward the passenger seat and was shot two more times, once in each leg. Some bullets missed or went through him and broke the passenger-side window. Yaras slumped down on a bundle of files and a calendar and died. The gunmen got back in the Chevrolet, driven by a third man also in a ski mask, and drove away. The car and license plates had been stolen earlier in the day Thursday from the suburb of Burbank. It was found a short time later found burning in an alley near North and Latrobe Avenues, about a mile northwest of the shooting. Witnesses told police they saw four men get into another car and speed away.

 Police searched Yaras office inside the laundry and found his appointment books for 1982, 1983 and 1985, but the 1984 book was missing. Yaras, born in 1941 when his father was at the top of his game in the Underworld, lived in a condo at 6400 N. Cicero Avenue in Lincolnwood Illinois, was a business partner with mobster Joe DiVarco. An hour before Yaras was killed, DiVarco, who was on trial for tax evasion and gambling charges, was ordered into federal custody as a danger to the community under a law that  prosecutors can ask that defendants be jailed immediately after conviction upon a showing that they pose a danger to the community, even if they have posted bail.

 Yaras was once regarded as a lieutenant to DiVarco but had moved up in recent years before his murder and operated on about the same level as DiVarco. While Yaras was the recognized gambling boss in the Rogers Park and north suburban areas, DiVarco ran mob gambling in the Near North Side nightclub area, including Rush Street.  Police suspected that Yaras had secretly provided information that convicted DiVarco. But federal investigators close to the DiVarco case insisted Yaras had nothing to do with it.    

 On April 18, 1974, Yaras brother Ronnie (Born 1938) a massage pallor operator in Miami Beach was shot dead by persons unknown n his house. Three months before, their father, Dave Yaras, suffered a heart attack while playing golf and died in Miami.   Yaras was probably the getaway driver in the January 20, 1983 murder of Allen Dorfman and may have been threatening the Outfit with telling what he knew or was killed simply because the Dorfman murder could be used in the case against Aiuppa and Cerone. The actual shooter in the Dorfman killing was said to have died of a drug overdose several months before in Florida. Police suspected he was murdered. 

Another theory was that Italian-American faction of the Outfit no longer wanted to work through Yaras, a Jew, to collect street taxes from Jewish bookmakers on the North Side and told Yaras to step aside but he refused. That theory was doubtful since the mob had always worked peacefully with virtually any ethnic group in as long as they delivered the money they were assigned to deliver. The murder was apparently inspired by Joe Ferriola who was racing towards the Outfit leadership and felt that the aging hoods before had to go. A Mob informant told the Chicago Crime Commission that Ferriola said, "Things are coming apart in Chicago and something has to be done about it."

Always paranoid, it was Ferriola’s belief that bookies and collectors were working together to hold out on delivering the correct street tax and that Yaras was the most blatant of the group.    David "Red" O'Malley, who was serving a 10-year sentence at the federal Metropolitan Correctional Center for an unrelated extortion conviction in May of 1985, was arrested and eventually acquitted in the Yaras murder, largely because the judge found too many inconsistencies in the prosecution witnesses who placed O'Malley at the scene of the slaying. The witness gave different accounts about the type of masks the killer was wearing And the color of the clothes he had on. Another witness testified that he had seen O'Malley drive away from the alley where the stolen Chevrolet had been found burned. But in the court room, when asked to identify the man he had seen leaving the alley, he couldn’t spot O'Malley, who sat at the defendant's table, five feet away. When asked a second time, he identified O'Malley but seemed to do it reluctantly.

 Another witness, a self-employed roofer, changed his testimony in mid stream and told the court he could identify O'Malley as the assailant because the assailant had been wearing a mask made of thin plastic that only partly concealed his face and then failed to identify O’Malley in court.

On February 10, 1985, just a month after Yara was killed, the body of gambler Hal C. Smith (Born 1937) was found in the trunk of his car in suburban Arlington Heights, Ill. He had been brutally beaten, and his throat was cut. Rumors were that he had simply stopped paying his street tax as a way of protesting the increase placed on him to defray the cost of Aiuppa’s upcoming trial.   

A prominent independent suburban bookmaker, Smith’s mangled body was found in the trunk of his champagne- colored Cadillac. He had been beaten, stabbed and strangled. (He died from strangulation.) He had vanished two nights before, telling his wife he was going to meet Outfit gambler Bill Jahoda in the Village Tavern restaurant in Long Grove. The site where Smith’s body was found, on the Elmwood Park side of Harlem Avenue, bordering Chicago, was unusual since most of the Outfits leaders lived near the area and preferred to keep crime out of the area. To make sure that was understood, in 1962 hoodlums Jimmy Miraglia and Bill McCarthy, both 24, inadvertently chased two men and a woman into Elmwood Park and killed them there. Both were later tortured and murdered by Outfit killers as a lesson to keep heavy crime away from where the bosses lived.

  In 1995, a full ten years after Smith was murdered, Robert Salerno, a onetime boxer and Outfit slugger, Rocky Infelise, Robert Bellavia and Salvatore DeLaurentis were convicted of conspiring to murder Smith.   It was a bizarre trial, even by Chicago standard.  Salerno was represented by his son,   defense lawyer Alexander Salerno said he was proud to introduce the defendant, "my father" at which point Salerno stood up at the defense table, bowed and said "Pleased to meet you, ladies and gentlemen."

"I wanted to help him not because he's my father” The younger Salerno told the court

“but because he's always helped me. I probably know him better than anyone in the world. I don't believe he killed anyone. He's always taught me to obey the law."

"I'm not an angel, but I did not kill this man," Salerno told the court

The key government witness was Bill Jahoda, the former newspaper man turned gambler turned mob informer. Jahoda said that not only had Smith refused to pay his $6,000 a month in street tax, he had fallen into a loud argument with mobster Salvatore Dé Laurentis in a suburban restaurant. Afterwards, Dé Laurentis waited for Smith in the parking lot and screamed at him “You, my friend, are trunk music."

He told the court that he lured Smith to his home in suburban Long Grove Illinois on orders from crew chief Rocky Infelise.  Jahoda said he didn’t know the Smith was marked for death, "But I knew it was a serious meeting.”   

Jahoda directed Smith to drive his car into the garage attached to Jahoda's home, and then directed Smith into his kitchen. He said that Rocco Infelise told him to make sure Smith entered the house alone. So Jahoda headed toward the curb on the pretense of picking up his mail.  Jahoda said he left the house and when he looked through a window outside his house, he saw Salerno, dressed in black, come up from behind Smith as he entered the kitchen. Later he said he saw that Smith had been knocked to the floor and dazed. The killers had slashed his throat, repeatedly punctured his body with a knife and then strangled him.

 At the prosecutor’s instruction during his testimony, Jahoda placed toy figures inside a model of his home to illustrate to jurors where Smith, Salerno and the others were in the kitchen when he peered inside. Jurors then walked past the model to get a closer look.

Four years after the murder, Jahoda began working undercover for the government. In one taped meeting with Robert Bellavia, who was also in the house when Smith was killed, Jahoda asked if Smith made it out of his kitchen alive. "No, that was it, right there. Out," Bellavia responded.   The prosecutor told the court "It was, in a word, sadistic, and it was meant to send a message.  For the defendant and others, this was strictly business, and unfortunately, it was business as usual."

   "I don't know why he put me there," Salerno said of Jahoda. "I fit the description, I fit the nationality."

Three days after Smith was found dead, on February 13, 1985, Chuckie English, (Born 1915 as Charles Inglesia) a onetime Capo under Sam Giancana was gunned down as he walked to his car in the parking lot of Horvath's restaurant, 1850 N. Harlem Ave., Elmwood Park.   Under Giancana, English was the Outfits boss of jukeboxes, gambling, counterfeit music recordings, coin-operated vending machines, gambling and juice loans on the West Side in the 1950s, 1960s and early 1970s. He had once owned Lormar Distributing Company, which sold phonograph records and tape decks but was largely a front for the collection of juice loans from gamblers. When, in 1950, English was called before the U.S. Senate Rackets Investigating Committee concerning the jukebox industry, then heavily influenced by the mob, he repeatedly took the 5th Amendment.

 Three years after Giancana's death, English was reported to be semi-retired, spending winters in the Hallandale, Fla., area, golfing and deep- sea fishing. During the summer and fall he ran small card games in Elmwood Park. Otherwise he lived quietly in a 10-room, two-story, Mediterranean-style home, with a swimming pool at 1131 N. Lathrop Avenue in River Forest. When English bought the home in the 1960s, a real estate agent remembered, he put down $5,000 as earnest money, and said: "There is a lot more where that came from."

He then peeled off more bills from several other large wads of money, the real estate agent recalled.   The rumors about why the 70 year old English was murder on the eve of St. Valentine’s Day were rampant. Some said it was because he was trying to expand his gambling rackets which is doubtful. Others claimed that a group of young Turks within the organization had gotten permission to take him out and take over his operations. Perhaps Ferriola himself ordered the murder or, as others speculated, the imprisoned Joey Lombardo because English was too quick to turn his street tax over to Ferriola who was obviously pushing his way to the top of the organization. But Ferriola’s dislike of English was legendary.

Chicago police noted that English had fallen out with the acting boss Joe Ferriola when they followed him to Bruno’s, a gasoline station frequented by the Outfit which was across the street from the Elmwood Park restaurant where English was gunned down. Detectives who were tailing Ferriola recalled "There apparently was a very cold relationship between English and Joe Ferriola, who likes to take over everything. English was there. So were other regulars, among them Dominic Cortina, Don Angelini and George Colucci. Ferriola shows up and here's what he did: He walked right past English. Didn't look at him at all. Goes right into the gas station like English wasn't there. That meant a lot to me. It showed who was strong and who wasn't. English stood around a while alone. Then he walked away, got in his Cadillac and left. The boys weren't talking to him."  

Patrick Healy, then the executive director of the Chicago Crime Commission, said, "This killing is out of character, sort of a mystery. He hasn't been in the mainstream of gambling activities, and that's what's been getting all the attention lately."

  English was a prime suspect in the 1975 murder of his old boss Sam Giancana in the basement of Giancana's Oak Park home. Conversely, there was another argument that claimed English was exiled because he had refused to set Giancana up for the killing, although it is almost a certainty that he either killed Giancana himself or directly assisted in the murder.   Investigators said it appeared that English had been trying to organize some independent bookies under his supervision and may have patched up, or was trying to patch up,  differences with Joseph Ferriola, who has been in charge of gambling for the mob. Ferriola, the cops said, had forced English to leave town right after Giancana was killed. It was common knowledge that English had been telling his friends that he, rather than Ferriola, should have been put in charge of suburban gambling.  English arrived at Horwath’s restaurant in suburban Elmwood Illinois, at about 3:00 AM.  Horwath's was firebombed bombed on May 4 and August 8, 1982, for reasons that never known. (It was closed and demolished in 2004 and is now a Staples Supply store) That afternoon at 3:30 PM, the restaurant’s owner, Charles Roumeliotis, served a roast pig for regular customers and had invited English to drop by to eat. Sharing the table with him were 13 other guests including two Cook County judges, Louis J. Hyde and Benjamin DiGiacomo as well as the village trustees Donald Storino and Louis DiMenna. Sitting with them was labor thug John Lardino. It was his birthday.

 English was a former client of DiGiacomo’s when he DiGiacomo was a lawyer in private practice. At about 6:00 PM, English stood, patted his stomach, hitched up his belt, waved goodbye and walked toward his white Cadillac De Ville coupe.  English left at about the same time as two other men, one of whom paid English's check, although they weren’t sitting at the table with him. One of the men, described as elderly and slumped, walked out with English but went to another car. As he reached for the car door, which was parked less than fifty feet from the restaurant, two men wearing ski masks pumped five shots into his body, one hitting him between his eyes, the forehead, nose, left eyebrow and right cheek, and once in the back, below the right shoulder.  

Two men, the killers, were in the parking lot waiting for him. Police impounded a car that witnesses said the killers were leaning on before the shooting. The killers left on foot and no shell casings were found on the scene, although several shots reportedly were fired, leading police to theorize that the murder weapon was a revolver, which does not eject casings. The government suspected that the gun or the silencer used in the killing was provided by Hans Bachoefer of Elk Grove Village who had a long history of dealing weapons.

Aiuppa’s skimming trial began September 23, almost two years to the day after the indictment against Aiuppa and the others was returned, although the hoods defense team had tried to delay the trial even longer, arguing that they needed additional time to study more than 4,000 hours of FBI surveillance tapes made from bugged telephones and hidden microphones during the four-year investigation.

 During those four years, the FBI followed money couriers from Las Vegas to meetings with mobsters in parking lots near Aiuppa's home in Oak Brook.   During the trial, other defendants and their attorneys treated Aiuppa with apparent respect and although he listened closely to testimony of mob informant witnesses, he more than often dozed off to sleep especially when FBI agents were on the stand.

Allan Ackerman, Aiuppa's attorney later told the appeals court that government lawyers used details supplied by an unnamed informant to obtain the conspiracy indictment against the defendants and that defense didn’t learn the identity of the informant until after the trial.  "Now, we're told there was” Ackerman later argued “and we find this crucial and devastating. This is the only witness in the entire case who testified that he physically put money in anyone's hands. We would have the right to investigate him, then question him before the jury." Assistant U.S. Attorney. Frank Marine replied "We have never publicly disclosed the name of the informant because of fears that he would be killed," Marine said. "There was definitely a concern for his safety."   

The informant was Carl Thomas, a Las Vegas casino owner, who testified that he took $80,000 in cash from a casino counting room and gave it to a Chicago mob emissary. He also told the jury that the skimming of gambling profits took place in five Las Vegas casinos that received millions of dollars in loans from the Teamsters Union pension fund in the 1970s. Thomas had been convicted earlier for his role in a scheme with Kansas City mobsters to skim from another Las Vegas casino, and he received a 15-year prison sentence. He also was indicted in the Stardust conspiracy, but charges were later dropped and his previous conviction was reduced to time served and probation.  

Among the key witnesses for the government was Glick, who purchased the Stardust hotel-casino in the fall of 1974 with a $62.7 million loan from the Teamsters Union pension fund. Glick testified that when he first inquired about a loan from the Chicago-based fund, he was told by a former official that "the man to see" was Frank Balestrieri, the boss of the Milwaukee Mob. He said that in early 1975, he learned that Nick Civella, then Kansas City's mob boss had also helped obtain the loan through his friendship with Roy Williams, then a Teamster trustee and later the union president. After Glick assumed control of the casino, Glick said he was threatened by Frank Rosenthal, a Chicago mob associate who ran the gambling operation at the Stardust and that Rosenthal ordered him to stay away from the casino and its day-to-day operations. Wiretaps backed up his story and showed that the Chicago mob hired and fired employees at the casino at will.

 On one tape, Las Vegas hood Tony Spilotro was heard on two tapes giving instructions to a hotel official to hire a friend. After Spilotro warned the hotel official that his friend had no casino experience, the official said, "That's all right. I'll put him on the graveyard shift at $22 or $23 ($22,000 or $23,000 a year)."

 On other tapes Spilotro was overheard calling hotel employees to give them names of those he wanted to receive free rooms, meals, drinks and floor show tickets at the Stardust. The microphones for the tape recorder was hidden inside the Gold Rush jewelry store, which Spilotro owned. Glick was eventually forced to sell his interest in the casino by the state of Nevada.  Teamster President Roy Williams also testified for the government on hopes that his testimony would get him a reduction in his 10- year prison sentence for his conviction in a bribery conspiracy case. It didn’t. One time Cleveland Mob boss Angelo Lonardo, already in prison on narcotics charges also testified for the government. His testimony implicated Rockman, his brother-in-law, in the conspiracy.

 In 1981, Jackie Cerone and Joseph Aiuppa and Angelo Lonardo and Milton Rockman from the Cleveland mob met in a hotel room to discuss who to name as the new president of the Teamster union. Frank Fitzsimmons, the union president, was near death from lung cancer, and a struggle was underway to find his successor. Cleveland wanted the job to go to Roy Williams, an international vice president. As part of the deal, Williams would name Jackie Presser, a vice president from Cleveland, to a powerful union post. But   Aiuppa and Cerone had their doubts about Presser, however the Cleveland hoods convinced them to give Williams and Presser a try if only because they could be easily controlled.  

 Aiuppa and Cerone objected to Presser because they felt they could not trust him. "They also felt that no one could talk to Jackie Presser and be able to get him to do what they wanted," he said. "Rockman told them not to worry about Presser, as Rockman could control Presser." But a day later, Rockman got a message that Chicago would support Williams. They were also right in not trusting Presser who had been informant for the federal government for more than a decade.

  On May 6, 1981, Frank Fitzsimmons died. Nine days later, the Teamsters executive board met in Las Vegas and elected Williams president. New Jersey Mafia boss Anthony Provenzano, a Teamster official, made the motion to elect Williams, and Presser seconded it.  A week after his election, Williams was indicted by a federal grand jury in Chicago on charges of attempting to bribe then-U.S. Sen. Howard Cannon (D., Nev.). Indicted with him was Chicago’s point man in the Teamsters, Allen Dorfman.  Presser provided the FBI with critical information that helped indict and ultimately convict Williams in late 1982. In 1983, after Williams was forced to resign as Teamsters president because of the felony conviction, Lonardo said he met Cerone again and told him the Cleveland mob wanted Presser to replace Williams.

  "Cerone still felt Ray was as good as Presser, but Cerone indicated that Chicago would go along with Cleveland and support Presser," Lonardo told the jury. So Jackie Presser was elected Teamsters president on April 20, 1983, after an intense lobbying effort in which he stressed the need to improve the union's image as a haven for mobsters.

Former Los Angeles Boss Aladena “Jimmy the Weasel” Fratianno took the stand at the trial for the government and said that in 1974, when Presser was still a lower ranking Teamster official in Ohio, he sent word to the Chicago Outfit that he was available to do them favors. Fratianno then recalled a 1974 meeting in a Chicago restaurant, when he told Joseph Aiuppa that "if you need anything from Jackie Presser, he said he'll do it for you."

 Fratianno had just returned from Cleveland at the time, where he had met with Presser to get approval to set up a union dental program in Warren, Ohio, with Allen Dorfman. "Aiuppa told me he didn't like Presser and that if he had any Teamster business, he would do it through Nick Civella in Kansas City and Roy Williams,"

At another meeting in Chicago, Fratianno said, he was told in 1976 by both Aiuppa and Cerone that "they didn't want anything happening in Las Vegas." He testified further that Aiuppa told him, "We have interests in casinos there, particularly the Stardust." Fratianno said he had to follow certain protocol whenever he wanted to see Presser. "I was told I had to go through Milton Rockman," Fratianno told the jury.  After 450 hours of testimony over 64 days, the case went to the jury of six men and six women. The verdict came after the jury had spent 30 1/2 hours deliberating over a four-day period.

On January 21, 1986 Aiuppa and all of the other defendants were found guilty of conspiring to hide their ownership of a Las Vegas casino and of skimming $2 million in profits. Chicago’s FBI Chief Edward Hegarty hailed the verdicts and described the case "as the most significant prosecution of organized crime figures in the history of the United States." While the case has been overshadowed since by other large convictions, it was a major blow to the Midwest mob and the organized crimes control over Las Vegas.

Aiuppa and Cerone showed no emotion as the judge read the verdicts which found the defendants guilty of all charges in the eight-count conspiracy indictment. It was the first time that Aiuppa had been convicted of a major crime.  

  Aiuppa, 80, and Jackie Cerone, 73, received the stiffest sentences, 28 years each. Angelo LaPietra, boss of Chicago's 1st Ward, was sentenced to 16 years; Joseph Lombardo, West Side crime boss, was sentenced to a 10-year term; and Milton Rockman, the Cleveland mob's financial adviser, 24 years. When the verdict was read, Aiuppa smiled and waved to friends in the courtroom.   Carl DeLuna, the Kansas City mob underboss, and Milwaukee boss Frank Balestrieri, pleaded guilty to the conspiracy as the trial progressed. Already serving a l3-year prison term for a Milwaukee extortion conviction, Balestrieri received a l0-year sentence, to be served concurrently, and a $20,000 fine but Balestrieri's two sons, Joseph and John, won a directed verdict of acquittal after arguing that the prosecution lacked evidence to convict them.

Working under what then a newly passed federal law, the prosecutors sought immediate imprisonment for Aiuppa and Cerone, saying that they poses a danger to the community if allowed to be free on bond. The affidavit alleged that Aiuppa, as boss of the Chicago organized crime family, ordered or personally approved the murders of 14 persons, including his predecessor, Sam Giancana, and Allen Dorfman, which was probably true. They were led away in chains to Leavenworth Penitentiary, 28 miles from Kansas City. Aiuppa came to court in casual clothes, as opposed to the suite he normally wore and handed his lawyer his watch, money and wallet before he left the courtroom.  When Chicago burglar Joseph Pops Panczko was sent to  prison and he spotted Aiuppa"

Aiuppa recognized me and I recognized him," Panczko said "I asked him how much time he has left and he said, 'Too much.' " Aiuppa entered prison in March of 1986, he was technically broke despite a 50 year criminal career. It was the gangsters hope that by appearing penniless the government would give up on its attempts to collect $143,000 in fines placed on him as part of his sentence. Aiuppa refused to tell investigators anything about his personal finances but federal investigators said they discovered that Aiuppa, apparently anticipating a conviction, placed an estimated $500,000 in real estate in the names of relatives while his trial was underway. He began transferring titles to his Oak Brook, Illinois home, five acres of adjoining property, three other parcels of land then worth $100,000 and two cars. (Although Aiuppa, continued to pay the $5,029 yearly property tax on his Oak Brook while he was in prison. The property remained in Aiuppa's name, although the tax bill was sent to a nephew.)

During the trial, Aiuppa mentioned to a reporter that he bought the five acres of land near his home for $5,000 an acre and that it was then valued at $50,000 an acre. In mob circles, Auippa was noted for his generosity, once picking up the tab for an entire wedding for a mobsters son.   An informant told the FBI that the Aiuppa’s share of the Las Vegas skimming was more than $200,000 a month.

He also collected hundreds of thousands of dollars in cash each month from gambling profits, and street taxes from bookmakers, burglars and loan sharks. David Helfrey, a Justice Department Strike Force attorney who prosecuted Aiuppa in the conspiracy, estimated that the stolen casino profits may have totaled more than $20 million during the four years that the FBI investigation was underway.  But that was all behind Aiuppa. In prison, he would be allowed to keep $10 in change for vending machines and another $95 in cash in a commissary account for personal items.

Due to his ill health, Aiuppa and the sickly Carl Civella of Kansas City were sent to the U.S. Bureau of Prisons hospital facility in Rochester, Minnesota which has a campus like setting as opposed to high walls and wires. The prison is close to the Mayo Clinic, just a mile away. By the time he arrived, Aiuppa health has worsened and he was walking with a cane.  There he would live in three-man rooms, each with a large picture window overlooking tree-lined walkways on the 50-acre wooded site on the southeast edge of Rochester. On weekends the prison showed films on videotape in the dayrooms of the facility's four residence buildings.  By 1987, the 80 year old Aiuppa’s health problems were so severe that occasionally he failed to understand even a simple statement from his attorney largely because of a condition that restricted the flow of blood to the brain.

By then he had only served two of his 28 year sentence. Towards the end, he didn’t know why he was in prison. Arthroscopic surgery on his left leg due to deterioration of his knee, made it virtually impossible for him to walk. He suffered from heart problems, phlebitis and cataracts.     In 1987, the US Appeals Court reaffirming his conviction in connection with the skimming of $2 million from a Las Vegas casino’s "The appeals court action has to be a signal to mobsters he once controlled that the boss is never coming home from prison," Patrick Healy, executive director of the Chicago Crime Commission, said. 

In January of 1996, Aiuppa was released for medical reasons from a Minnesota prison hospital. Aiuppa’s wife, Angela, died in 1983 and he was cared for by his nieces and nephews in his home at 4 Yorkshire Drive in Oak Brook where he had lived since 1957.  Auippa and died shortly after being released from prison at the age of 89 from the effects of throat cancer and heart disease.