Ronald Zellman. More complications occurred in the organization when Vito Spatafore, the top earning captain of the Aprile crew and cousin-in-law to Phil Leotardo, fled New Jersey after his homosexuality was revealed. Tony finds out that his cousin wants a bigger share of responsibilities, while Finn makes an embarrassing discovery about Vito. Junior was judged to be mentally unstable and was sent to a mental rehabilitation facility. When Jackie Aprile was diagnosed with cancer in 1998, his closest friend—Junior's nephew Tony Soprano—took over Jackie's responsibilities to Junior's displeasure. Tony, realizing that Phil was sending the message that New York can do whatever they want, decided to hurt Phil financially as payback for Vito. Bobby Bacala is killed at a model train shop when two assassins ambush him. He, along with Vito Spatafore and Donny K., found Gigi Cestone dead on the toilet in the Aprile Crew hangout after suffering a constipation-induced heart attack. Tony refused at first, but had a change of heart after talking to Johnny Sack at his daughter's wedding. In an attempt to clear the air between them, Tony paid a visit to Phil's hospital bed, telling him of his own near-death experience. Tony conducted the execution of Millio with caution, bringing in two men from Naples to carry out the hit on Rusty and his soldier, Eddie Pietro. He states to his friends that, "The only thing I ever found in the street was my first wife," showing that he hasn't had much good luck in his life (and at least one failed marriage). In the meantime, the Soprano Family continued to stay in a period of transition, with Richie Aprile, older brother of Jackie Aprile, taking over the previously defunct (due to the death of Jackie Sr.) Aprile crew after his release from prison in 2000. With James Gandolfini, Lorraine Bracco, Edie Falco, Michael Imperioli. Eugene reveals his mean streak once again in the episode "Eloise" when he and another associate engage in jury tampering, in which they are sent to intimidate a juror who is on Junior Soprano's trial. Tony reasoned that a war with New York would prevent his family from earning. New York convinces Burt Gervasi to switch sides, and he approaches Silvio Dante to join in on a coup d'état attempt on Soprano. Tony and some soldiers head to a safe house to hide, as the search for Phil continued, and Tony attempts to sleep while holding the AR-10 rifle in his arms, which Bobby gave to him on his 47th birthday, surrounded by bodyguards. Both Johnny Sack and boss Carmine Lupertazzi blamed one another for the conflict, and reached out to Tony to whack the other as a means of ending the conflict. Bonpensiero, also a close friend of Johnny Boy's son, Tony Soprano, would make his bones by killing a small time bookie, as seen in Walk like a Man and become a made man shortly thereafter. Junior's increasingly diminished capacity led him to shoot Tony in the abdomen, mistakenly thinking that Tony was former already deceased nemesis "Little Pussy" Malanga.

Disagreements over the split of the money of the Esplanade, plus the HUD projects that Tony was keeping secret from Lupertazzi and the displeasure of Johnny Sack with Ralph Cifaretto, nearly caused the two families to go to war. Carlo Gervasi was named by Tony as the replacement point man for the Family's construction interests. It becomes clear that there is no compromise available between NY and NJ, and as a result the wheels begin to move. Eugene Pontecorvo, played by actor Robert Funaro, is a fictional character in the HBO television series The Sopranos. During the early 1980s many DiMeo crime family members and associates were arrested, causing the biggest blow to the family since its formation. After a sit-down between the New Jersey and New York Families, a truce was nearly reached before a reference from Little Carmine to the death of Billy Leotardo resulted in Phil Leotardo storming out. His jobs include running a low stakes poker game, a sports betting agency and a'No Work' job at the Esplanade construction site. It wasn't long before Walden Belfiore, a Soprano Soldier, caught up with Phil at the gas station. He dates Tony Soprano's former mistress Irina Peltsin but she later broke up with Ronald due to when Tony whipped Ronald with a belt and humiliated him in front of Irina. Ronald Zellman was an Assemblyman and acted as a political operative on an interest of the Soprano Crew.He aided them in securing the Esplanade construction contract. After Raymond Curto dies of a massive stroke while giving potentially damaging information to Agent Robyn Sanseverino about Tony discussing a murder, the F.B.I. Vito instructs an overwrought Eugene to take the rest of the day off. Like Vito Spatafore and Benny Fazio, he is initially introduced as a small character, whose role slowly increases throughout the series.

Uncle Junior and Tony were at that point at each other's throats because Junior plotted to murder a rival, "Little Pussy" Malanga, in Malanga's favorite restaurant, Vesuvio, a restaurant owned by Tony's childhood friend Artie Bucco. Johnny Sack later plead guilty in his RICO trial to lessen his sentence, thus making Phil Leotardo the boss in all but title. Junior managed to beat the disease before the RICO trial against him started. Although mild-mannered, Eugene has a tendency to lose his temper, similar to Ralph Cifaretto.

Caught by the police, Tony B. ended up spending 17 years in jail, while Tony became one of the top earners in the DiMeo Family. With Tony and the Feds both hindering Eugene's chance to escape the mafia life and his stress caused by his unstable home life, Eugene sees no way out and hangs himself in his basement.

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