October 6th, 2008. East Farmingdale, Long Island. Federal agents were digging through dirt and brush when the ground finally gave back a secret the Colombo family had tried to bury for 9 years. A human skeleton was found wrapped in tarp, still wearing shoes. The FBI confirmed the remains belong to William “Wild Bill” Cutolo, the missing Colombo underboss.
The medical examiner called it homicide. The street had known for years that Bill was dead. Now the dirt was talking, too. This wasn’t a small-time gangster. Cutolo was underboss of the Colombo crime family, a man with money on the street, a crew waiting for him every Wednesday night, and enough respect inside Brooklyn to make bosses nervous.
He had survived the bloody Colombo war of the early 1990s. He had backed the wrong faction, fought the Persicos, then somehow walked back into the administration. That alone made him dangerous. This is the story of how a mafia underboss went to meet the acting boss on May 26th, 1999, and disappeared. It is about power, old grudges, loan shark money, a social club dinner that never happened, and a family that was threatened into silence after their father vanished.
But here is what makes this case different. Wild Bill wasn’t killed because he was weak. Prosecutors said he was killed because he was getting too powerful inside the mafia. That is the worst kind of strength. To understand why the Colombos turned on him, you have to understand the world Cutolo came from. The Colombo family was never the calmest of New York’s five families.
It was a family with a name problem, a succession problem, and a civil war problem. Carmine “the Snake” Persico was the official boss, but he was locked away. His son, Alphonse “Allie Boy” Persico, wanted control. Victor Orena, the acting boss, had his own followers and did not want to step aside. Cutolo chose Arena.
That choice followed him for the rest of his life. During the early 1990s, the Colombo family split into two armed camps. The Persico side and the Arena side fought for control. Court records describe about a dozen killings during that war, plus arrests that drained the family of manpower. Cutolo was on the Arena side trying to rest power away from Carmine Persico and Ally Boy.
When the war cooled down, it did not really end. The bodies stopped dropping so often, but the memory stayed alive. That is how mafia politics works. You can shake hands, you can sit down, you can call it peace, but the old ledger stays open. Cutolo was not just a gunman in that world. He was an earner.
He knew how to move money through street loans, crews, union influence, and social club discipline. On the surface, the operation could look simple. A guy gets money, he puts it out on the street. Borrowers pay weekly interest. If the borrower misses, the pressure comes. If the collector lies, he pays a tax.
If somebody uses the wrong name, the violence becomes the receipt. Here is how it worked in Cutolo’s orbit. Giovanni Floridia, known as John the Barber, was involved in loan sharking with money that came through Colombo associates. Cutolo learned his name was being used and that he was not getting his cut. Floridia was asked how much money he had on the street.
The real number was about $300,000. He claimed it was only $80,000 to $100,000. Cutolo found out. Then, Cutolo confiscated $50,000 Floridia expected from a robbery and taxed him another $25,000 for lying. That is not just greed. That is management by fear. Cutolo was teaching everyone around him a rule. If his name created money, he owned part of it.
But the same system that built him also built resentment. Floridia was furious. Other men believed Cutolo was too harsh. Joseph Campanella, a Colombo soldier who had known Cutolo since childhood, owed him about $300,000 from loan-sharking money advanced years earlier. When Campanella bought a Mercedes instead of paying back the debt, Cutolo was angry enough that there was talk of smashing the car windows.
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In the regular world, that is a money dispute. In the Colombo family, it could become a murder motive. John Jackie D’Amico is the man you have to watch. D’Amico had history with Cutolo. Court testimony said D’Amico had proposed Cutolo for membership in the family. He had helped bring him in. Then D’Amico went to prison for about 8 years.
When he came home, the relationship had changed. Cutolo was no longer under him. Cutolo was above him. That kind of reversal burns inside a mafia man. The guy you once sponsored becomes your superior. The man who used to look up now gives orders. D’Amico resented it. By about 1998, the commission backed the Persico faction.
Allie Boy Persico became acting boss. Cutolo became acting underboss. On paper, that looked like reconciliation. In reality, it put the former enemy inside the administration. Close enough to watch and close enough to remove. Cutolo had what mobsters call boss mentality. Michael Di Leonardo, a Gambino captain who dealt with the Colombos, later testified that Cutolo had momentum behind him and wanted the main hat.
He warned Persico that Bill had boss mentality. That phrase mattered. It did not mean Bill was ambitious in a normal way. It meant he might not give power back once he had it. Allie Boy had another problem. He had been arrested on a gun possession charge and was expected to go back to prison. If he disappeared into a federal cell, who would control the family outside? A quiet underboss might preserve the throne.
Wild Bill Cutolo was not quiet. This is where the murder begins before the murder. In mid-April 1999, DeRoss asked Campanella how he would feel about killing Wild Bill. Campanella later testified that DeRoss was serious. He refused. Around the same period, Floridia heard from Vincent Chickie DeMartino that Cutolo would not be around much longer.
DeRoss then told Floridia not to worry and said things were going to change. That is how plots move in the mob. Rarely does a boss say everything in clean language. They test people. They ask a question. They watch the reaction. They create distance between the order and the trigger. The opportunity came on Wednesday, May 26th, 1999.
Wednesday mattered in Cutolo’s routine. He usually went to a Manhattan union office that day. He also had his regular Wednesday evening gathering at the friendly bocce social club in Brooklyn, where members of his crew assembled and expected him to show. The day before, Persico and Cutolo paged each other several times and spoke by phone.
That night, Cutolo was upset because a planned appointment had been moved from Tuesday to Wednesday. On Wednesday, around midday, his wife Peggy paged When he called back, she later testified, he said he had to go to Brooklyn to meet the kid. She understood that to mean Allie Boy Persico.
The meeting place was 92nd Street and Shore Road in Bay Ridge, Brooklyn. According to Peggy, her husband had told her he habitually met Persico there near an overpass where they could avoid FBI surveillance. Just picture that detail. Not a restaurant, not a club, not a formal sit-down with witnesses, an overpass, stone steps, a place chosen because eyes would have trouble following.
In the early afternoon, Cutolo drove toward Brooklyn. His car was having problems, so he took it to a repair shop. At his request, the mechanic drove with him to 92nd Street and Shore Road. At about 3:15 in the afternoon, the mechanic dropped him near the park and took the car back for repair. Cutolo said he would pick up the car around 5:30. He never came back.
What happened after that point has never been cleanly described in public court records. The government proved that Persico and DeRoss ordered and arranged the murder. It did not prove that either man personally pulled the trigger. That distinction matters. In the mafia, the order can be more important than the weapon.
The next scene is one of the coldest parts of the entire story. That evening, Cutolo’s crew waited at the Friendly Bocci Social Club for the usual Wednesday dinner. Wild Bill did not show. He did not call. That was not his routine. His son, William Cutolo Jr., tried to reach him. The anxiety started spreading through the room. DeRoss was there watching the crew.
When Bill failed to appear, DeRoss acted surprised and told Cutolo Jr. to call his father. But according to prosecutors, DeRoss already knew what had happened. That is the performance inside the performance. The man tied to the plot watches the victim’s crew realize their boss is gone.
Early the next morning, May 27th, DeRoss arrived at the Cutolo home around 5:00 or 6:00 in the morning. He did not organize a search. He did not ask where Bill might have gone in the way a worried friend would. According to Peggy Cutolo, he demanded records and papers. She understood that to mean the books of loan shark money, the records of who owed what, and the cash behind the crew.
This is the second scheme in the story. After the murder came the takeover. Street money is not just cash. It is a map of power. If a book says one man owes $20,000, another owes $50,000, and another owes $300,000, whoever controls that book controls the pressure. The debt survives the dead man. The new administration wants the paper trail because the paper trail becomes income.
DeRoss kept coming back. He searched the office, bedrooms, attic, drawers, cabinets, bookshelves, furniture, and walls. Peggy knew there were records and money hidden in the house. Court records say $1.65 million was hidden in a vent above the stove and in tubing in the attic. She stonewalled him. That hidden money tells you everything about Wild Bill’s power.
A man with $1.65 million inside the house is not a ceremonial underboss. He is running real money. He has loans on the street. He has people paying tribute. He has enough liquidity to survive pressure or fund a move. That is why the fear of him taking over made sense inside mob logic. After Cuttolo vanished, the Colombo family did not act like an underboss was missing.
There was no serious internal investigation. In Mafia tradition, if a high-ranking member disappears without authorization, the family is supposed to ask questions. Other families listen. Liaisons talk. Nobody wants an unauthorized killing to start another war. But here, the machine moved straight to business.
DeRoss summoned crew members and asked about the state of the money. He was soon introduced as the new underboss. Campanella’s $300,000 debt to Cuttolo was erased. That was not mercy. That was politics. Cancel the debt, quiet the anger, and turn a potential witness into a man with something to lose.
But the family still had a problem. The Cuttolos knew too much. Peggy knew Bill had gone to meet the kid. Barbara Jean, Cutolo’s daughter, had her own suspicions. William Jr. knew his father would not simply walk away from his family, his money, and his crew. So, the third scheme began. Witness tampering.
Months after the murder, in March 2000, William Cutolo Jr. secretly recorded DeRoss threatening the family. DeRoss ordered them to help Persico by giving false information to a private investigator. He warned them not to talk to the law. He spoke about the little kids, Barbara Jean’s daughters, who were 7 and 5. That is not a casual warning.
That is the Mafia pushing fear through the next generation. You have to understand the cruelty of that. Wild Bill chose the life. His family did not choose to become evidence in a federal murder case. But once he vanished, they were dragged into the same machinery. First, the killers took the father. Then they tried to control the widow, the son, the daughter, and even the grandchildren through fear.
There is one more human detail that matters. Cutolo’s house was not just a gangster’s office with hidden cash. It was also a family home. Peggy had been his wife for about 30 years. Betty Ann Fox had been his girlfriend for about 20 years. His children lived with the consequences of both his public reputation and his private absence.
That is the contradiction in these stories. The same man who could terrorize borrowers and punish crew members could also leave behind people who waited for a phone call that never came. The mob likes to pretend those worlds are separate. They are not separate. They collide at the kitchen table.
For years, the case had a problem, no body. Defense lawyers understood what that meant. If there is no body, they can argue the victim may be alive. Maybe he ran. Maybe he went on the lam. Maybe the government built a murder case out of gossip and fear. Prosecutors had to prove death without remains, and that is not easy. They used behavior.
DeRoss demanding the books within hours, no real search by the family, statements from mob witnesses, the transfer of power, the canceled debt, the threats to the Cutolo’s. The pattern showed that everyone in the Colombo leadership acted like Wild Bill was dead because they knew he was dead. There was also a $50,000 notation found in Persico’s apartment.
Prosecutors connected it to DeMartino 1 month after the disappearance. The government argued that DeMartino had been involved in carrying out the order. But even here, the court later made the key point. The exact shooter was not the center of the case. The center was who ordered the murder and why. On December 28th, 2007, after an 8-week trial in Central Islip, New York, a federal jury convicted Alphonse Persico and John DeRoss of murder in aid of racketeering and witness tampering.
The verdict said the old Colombo war had never really ended. It had only waited for a quieter moment. Then came the twist. In October 2008, before sentencing was complete, agents found Cutolo’s body buried in Farmingdale. This contradicted one piece of the government’s trial theory because prosecutors had argued his body was likely dumped into the Atlantic Ocean.
Defense lawyers asked for a new trial saying the discovery undermined the government’s case. But the court rejected that argument. The burial site changed the disposal theory, not the murder order. The evidence still showed that Persico and DeRoss arranged Cutolo’s death. On February 27th, 2009, both men were sentenced to life imprisonment.
The life sentences closed the courtroom chapter, but they did not erase the message.
