He was one of the most disliked mob bosses of all time, with a superiority complex second to none. However, if Paul Castellano had been street-smart like any Mafia boss should be, he might not have been executed so easily and so publicly.
Paul Castellano was born Constantino Paul Castellano on June 26, 1915, in Brooklyn, New York. Castellano did not like his given first name, so he insisted that everyone call him Paul instead. Castellano’s parents were both born in Sicily, and his father was a butcher, with a little illegal numbers business on the side. Castellano’s father was also a early member of the Mangano Crime Family, which was created by Salvatore Maranzano after the killing of Joe “The Boss” Masseria, and the ending of the Castellamarese War.
Castellano dropped out of the school after the eighth grade and went to work in both of his father’s businesses. In 1934, when Castellano was only 19-years-old, Castellano and two of his buddies decided to commit an armed robbery of a local business. However, things went awry, and when the police arrived on the scene, his two friends escaped, but Big Paul, as he was called (Castellano was six-foot-three, and in his prime weighed over 275 pounds), was caught by the police. Castellano refused to rat on his colleagues and was hit with a three-month bit in the slammer. When he returned to the mean streets of Brooklyn, Castellano’s reputation was enhanced by his refusal to cooperate with the police.
In 1937, at the age of 22, Castellano married his childhood sweetheart Nina Manno, who was the sister-in-law of Carlo Gambino. They eventually had three sons — Paul, Philip, Joseph, and a daughter Connie.
In 1940, Castellano was inducted as a made member of the Mangano Crime Family, the same crime family his first cousin Carlo Gambino was already a captain in. In fact, Castellano and Gambino were so close, Gambino even married Castellano’s sister Catherine (marrying first cousins was not uncommon amongst the Sicilians). After Mangano was knocked off in 1951 by his underboss Albert Anastasia, Anastasia took control of the Mangano Family and changed the name to the Anastasia Family. Anastasia also bumped up Big Paul to the ranked of captain. In 1957, when Anastasia was killed by rival Vito Genovese, Gambino took over the Anastasia Family, changed the name to the Gambino Family, and inserted his cousin Paul Castellano as one of his right-hand men.
November 17, 1957, Genovese called for a huge summit of all the Mafia men in America to take place in Appalachian, New York, at the home of Mafia member Joseph Barbara. There were several items on Genovese’s agenda, but the most important one was to declare himself “Capo Di Tutti Capi,” or “Boss of All Bosses.” However, the wily Gambino knew that the local state police would be tipped off to the meeting, so he stayed away, and instead sent his cousin Paul to take the heat. When the state police raided the Barbara residence, dozens of mobsters tried to escape by jumping out of windows and running through the woods in their expensive suits and patent leather shoes. But not Castellano. Big Paul surrendered without a fight, and was sentenced to a year in prison for refusing to tell the police the purpose of the meeting.
After his marriage to Nina, Paul prospered in the family meat businesses, and by the 1950’s, he owned several businesses, including Blue Ribbon Meats, Ranbar Packing Inc., and The Pride Wholesale Meat and Poultry Corporation. According to Jonathan Kwitney’s book Vicious Circles, “The Castellanos owned many meat stores and distributorships in Brooklyn and in Manhattan. They had a long record of welching on debts; of suffering suspicious hijackings, which can lead to insurance claims; of selling goods that were later found to have been stolen off docks or trucks, and of cheating other firms by receiving the assets of companies about to go into bankruptcy proceedings.”
Whereas Castellano gave the airs of a successful businessman, issuing a death warrant was certainly not beneath his character. Castellano once ordered the death of an underling, because the man had the audacity to say Castellano looked like chicken magnate Frank Purdue (Perdue was famous for his chicken-like face splashed across the screen in his TV commercials, where he pronounced, “It takes a tough man to make a tender chicken.”). In the mid 70’s, Perdue was having trouble getting his chickens in the New York City weekly supermarket advertisement circulars. Someone whispered in Perdue’s ear, and soon he signed a distribution deal with Dial Poultry, owned by two of Castellano’s sons. From that point on, Perdue had no trouble advertising and selling his chickens in the New York market.
To show he would not allow anyone in his blood family to be abused in any way, Castellano’s son-in-law Frank Amato disappeared from the face of the earth after Castellano discovered Amato was beating Castellano’s pregnant daughter Connie, and cheating on her on the side. As a display of familial compassion, Castellano did wait for his daughter’s divorce to become final before he gave the order to vaporize Amato.
Castellano, with the blessing of his cousin Carlo Gambino, was also heavy into the loansharking busin then threw the book at Berardelli, sentencing him to five years in prison for contempt-of-court.
By 1975, Carlo Gambino was obviously very ill from a severe heart condition. If Gambino died, the favorite on the streets to take over the Gambino Family was Aniello Dellacroce, a hardened criminal and Gambino’s second-in-command. Dellacroce was a respected man, who had allegedly taken part in several “pieces of work,” or murders, and according to Mafia rules, was, in fact, supposed to be promoted to boss instead of Castellano. Dellacroce had the backing of all the major Gambino street crews, including Carmine Fatico’s men at the Bergin Hunt and Fish Club in Queens.
However, Gambino wanted to keep things in the family, and to the consternation of many, he anointed Paul Castellano to be his successor as the head of the Gambino Family. As a result, there was outrage from the street soldiers, who saw Castellano as nothing more than a greedy snob, who thought he was stratospherically above the common street soldiers who were kicking up all the money to the bosses up top. Whereas most captains demanded 10% of the street soldier’s take, Castellano wanted 15% of any scheme his men were involved with.
Things came to a head, when on October 15, 1976, Carlo Gambino finally died and Castellano was officially inducted as the Gambino boss. Street men, like tough John Gotti, bristled at the choice, and were hardly placated when Dellacroce, as a consolation prize, was given control of all of the lucrative Manhattan Gambino street rackets. Dellacroce, an old school Mafioso, who went by the credo that a bosses’ word should never be challenged, was he only person who was keeping his crew from a devastating and bloody mutiny against Castellano and his allies.
Whereby Gambino had lived in an inconspicuous house in Brooklyn, Castellano build himself a mansion on trendy Todt Hill in Staten Island. Todt Hill, which meant in Dutch “Death Hill,” was the highest track of land in the entire borough of Staten Island. The 17-room house was build with stone and stucco, and was painted entirely white, with two white columns majestically standing out front, looking suspiciously like the White House in Washington, D.C (The Gambino street crews snidely referred to Castellano’s home as “The White House.”). The house was completely surrounded by tall wrought-iron fences, and armed with the most sophisticated of burglar alarms. If this wasn’t enough to discourage intruders, Castellano had ferocious Dobermans patrolling inside the perimeter, viciously leaping at the fences if anyone, including the mailman, came near the house.
In 1979, 35-year-old Columbian Gloria Olarte went to work for the Castellanos as a housemaid. At the time Paul Castellano was 64-years-old, and his wife Nina — a very attractive 60-years-old. But that didn’t stop Paul Castellano from having a roving eye. Soon he started an affair with Olarte right under his wife’s eyes, and also in front of his daughter Connie, who was living nearby. Whenever his wife and Connie went out shopping, Castellano made sure they had enough cash to spend, so that they wouldn’t return home anytime soon.
At first, Castellano’s advances where just petting and simple kissing, and soon Olarte began to wonder why Big Paul had not consummated their relationship. It seemed that at the time Olarte made her way into the Castellano household, due to a diabetes condition, Castellano had not had an erection in four years. That problem was taken care of when Castellano has “the operation”: a penile implant that would make him able to have intercourse with his young housemaid.
His affections for Olarte were obvious to the crew members who visited Castellano for business meetings, and were also obvious to his wife. Gambino family members began talking amongst themselves about Castellano behind his back; about how he was disgracing his wife, by prancing his young housemaid in front of them at their “White House” meetings.
The FBI had been wanting to plant a bug in Castellano’s house for many years. Through conversations they overhead from bugs planted in other mob hangouts, the FBI had ascertained that when men came to visit Castellano to discuss family business, these meeting always took place in a little dining nook in the kitchen. There is some dispute as to whether Olarte herself, realizing that Castellano’s affections for her were waning, told the FBI where to plant the bug or not. But on March 17, 1983, while Castellano was on a Florida vacation with Olarte and his trusted aide Tommy Biloti, the FBI decided the time was ripe to plant the bug. The only problem was, Castellano’s wife was still on the premises.
When Nina Castellano finally left the house at around 5pm that afternoon, a team of FBI agents disguised as gardeners, sanitation workers, and telephone installers went to work. The “gardeners” drugged the Dobermans who were standing guard inside the fence, by throwing drugs-infested steaks over the fence for the dogs to consume. Then FBI “techies” disabled the burglar alarm, allowing three more “techies” to pick the door locks, then enter the Castellano residence. Two Sanitation trucks blocked the entrance to the street, and the FBI agents in the trucks disguised as sanitation workers were under orders to stop Nina Castellano, by any means necessary, from returning to the house until the bug was planted and the FBI agents safely out of the house.
Once inside the house, the agents went directly to the kitchen nook. By the table sat a chrome lamp near Castellano’s high backed chair, which he always sat in during mob meetings. The agents removed the base of the lamp, and replaced it with an identical base that contained a microphone, and a power pack. They placed the lamp back in is original position and quickly exited the house. Their stay inside the Castellano resident lasted only 12 ï½½ minutes. Once safely outside, the outside FBI “techies” re-activated the burglar alarm, so that when she returned to her home, Nina Castellano would be none the wiser.
These bugs became a treasure trove of information for the FBI. The FBI was, under law, supposed to stop listening when the conversations being recorded involved inane personal matters. But that was not always the case.
Within a few days, they heard Castellano boasting to one of his associates, “No one comes to Staten Island unless I say so.”
The bug in the Castellano residence lasted 4 ï½½ months. During this time Castellano was heard discussing how he was controlling the construction business, the meat packing business, and the labor unions; specifically the Teamsters, the painters union, and various unions related to the restaurant business. Castellano let the feds know he was also involved in the pornography business, as well as stock frauds, and insurance frauds.
These tapes decisively revealed to the feds that there were two factions within the Gambino Family, each of which had no use for the other. Castellano had the support of Bilotti and his cousin Tommy Gambino, who controlled the garment center in Manhattan. While the other faction was led by Dellacroce, and Dellacroce’s “favorite son” — John Gotti.
One of Gotti’s underling was Angelo “Quack Quack” Ruggiero, a rotund, boisterous man who got his nickname because he couldn’t stop talking; on the phone, or in places that were most likely bugged by the FBI. When Ruggiero was arrested in a big heroin deal, Castellano was incensed that any of his men would dare to sell “babania,” which was forbidden in the Gambino Family, and supposedly all throughout the American Mafia. Castellano immediately called Gotti on the carpet and reamed Gotti a new one, saying, “Listen Johnny, you got to prove you weren’t involved.”
Gotti knew that this meant if Ruggiero was indeed guilty of selling dope, and if Gotti knew about Ruggiero’s involvement, it was a death sentence for both men.
Soon, Castellano discovered from lawyers involved in the case that Ruggiero had been caught on secret recordings bragging about several drug deals. Castellano demanded that Ruggiero turn over the tapes to him, and when Ruggiero refused, Castellano (on tape) went berserk, threatening to do bad things to both Ruggiero and Gotti. This is when the FBI decided to lower the boom on “Big Paul.”
On March 25, 1985, FBI agents Andris Kurins and Joseph O’Brien made a trip to the Castellano’s “White House,” and told Castellano his was being arrested on RICO charges (Racketeer Influenced and Corrupt Organizations Act). Castellano seemed quite confused when he heard the charges, because he fully didn’t understand the implications of RICO.
Under the RICO Act, a person who is a member of an enterprise that has committed any two of 35 crimes-27 federal crimes and 8 state crimes-within a 10-year period, can be charged with racketeering. The RICO Act “allows for the leaders of a crime syndicate (family) to be tried for the crimes which they ordered others to do or assisted them to do, closing a perceived loophole that allowed someone who told a man to, for example, commit murder, to be exempt from the trial because they did not actually do it.” Those found guilty under the RICO Act can be fined up to $25,000 and sentenced to 20 years in prison per racketeering count.
So Castellano, at the moment of his arrest, oblivious to the fact that his house had been bugged for more than four months, did not realize the scope of the indictment he was about to face. According to Kurins and O’Brien, Castellano first heard of the taped conversations recorded in his house on the federal car radio, while the two feds were transporting Castellano from the “White House” to the “Big House.” After hearing the news on the radio, Castellano told the two feds he suddenly felt ill, and would they please stop the car at a drug store to buy him some Tums, and a candy bar for his diabetes, which was suddenly making his head swim.
However, Castellano was not the only mob bigwig arrested that day. Under the direction of Rudolph Giuliani, the US Attorney for the Southern District of New York, as the cuffs were being put on Castellano, they were simultaneously being put on Gambino underboss Aniello Dellacroce, Fat Tony Salerno, the head of the Genovese Crime family, Lucchese boss Tony “Ducks” Corallo, Columbo boss Carmine Persico, and Rusty Rastelli, the acting boss of the Bonanno Crime Family. Giuliani went so far as to arrest eighty-two-year-old Bonanno Family patriarch Joseph Bonanno in his home in Tuscon, Arizona. It seemed that Giuliani was astounded and overjoyed after reading Bonanno’s recent autobiography “Man of Honor,”where Bonanno admitted things about the “Sacred Society” that no made man ever dared utter.
In addition to the RICO charges, Giuliani hit Castellano with an additional 51 charges stemming from the murders and stolen car ring perpetrated by Roy Demeo’s crew. (Rumors were that before Castellano was arrested on RICO charges, he heard from his law enforcement moles about the impending Demeo-related indictments. Feeling that Demeo, facing life in prison, was not the type of man to do his time quietly, Castellano ordered the murder of his most proficient murderer. Demeo’s own crew did the honors; stuffing his frozen body into the trunk of a car for the police to find.)
Though an FBI informant close to Johny Gotti (code name Wahoo – later discovered to be longtime Gotti pal Willie Boy Johnson)), the feds found out that Castellano, because of the internal strife in the Gambino Family, was planning to whack Gotti and his entire crew. Gotti, cognizant of this sober fact, started tomake plans to do away with Castellano first. The only person that was stopping Gotti from doing what he wanted to do was Gotti’s boss Dellacroce, again an old-schooler, who would never sanction a hit on his own boss. This obstacle was removed on December 2, 1985, when Dellacroce finally succumbed to the ravages of cancer.
With the coast now clear for Gotti, Gotti sought permission from the other mob bosses to whack Castellano, before Castellano whacked him. Vincent “The Chin” Gigante issued a firm no to Gotti, but the other mob bosses, not liking Castellano too much, shrugged their shoulder and basically said, “Do what you got to do.”
On December 16, 1985, after finishing a 2:30 p.m. appointment in Manhattan with his lawyer James LaRosa, Castellano decided to kill a little time Christmas shopping with his chauffeur Tommy Bilotti, before they went to their 5 p.m. appointment at Sparks Steakhouse at 210 East Forty-Fifth Street. At Sparks, Castellano and Bilotti were supposed to meet with Gotti and three other men. A table for six had already been reserved for 5 p.m. under the name “Mr. Boll.”
According to several published reports, what Castellano didn’t know was that Gotti had no plans to show up inside Sparks Steakhouse, but was in fact at this time in the passengers seat of a Mercedes driven by Salvatore “Sammy the Bull” Gravano. Gravano parked the car at the corner of Forty-Sixth Street and Third Avenue, where he and Gotti had one eye trained on the entrance to Sparks, and the other eye trained on Third Avenue, waiting for Castellano’s black Lincoln to make its appearance. On the street surrounding Sparks were anywhere from eight to ten of Gotti’s men, armed with guns and walkie-talkies, ready to take action.
At approximately 5:30 p.m., with Castellano now fashionably late, Castellano’s Lincoln made the turn from Third Avenue onto Forty-Sixth Street, and parked in front of Sparks. As soon as Bilotti exited the driver’s side, he was met by a hail of bullets, allegedly fired by Gotti henchman Tony “Roach” Rampino, rendering Bilotti quite dead. As Castellano was exiting on the passenger side, he turned toward the street to see what all the commotion was about. Before Castellano knew what was happening, another Gotti shooter, allegedly John Carneglia, pumped six bullets into Big Paul, thus ending the reign of Paul Castellano as the head of the Gambino Crime Family.