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Jackie Aprile, Jr. was born into North Jersey mafia royalty. His father, Jackie Aprile, Sr., was once the acting boss of Northern New Jersey, and his uncle Richie Aprile was a capo first under Ercoli 'Eckley' DiMeo, and then later under Tony Soprano. However, despite his lineage, Jackie, Jr. himself was kept away from the family business by his father and when he did get involved proved a lightweight. He only began getting involved with the criminal aspects of his family in after the death of his father and the release of his uncle from prison. Despite attempts to succeed at Rutgers, Jackie, Jr. drifted towards a life of crime as he began helping his uncle Richie with business.However, Richie was killed by his fiancee Janice Soprano and for a time thereafter, Jackie was back on the straight and narrow. He went back to school and tried to work hard, but was unable to do well. At this point, his mother Rosalie Aprile began a romantic relationship with Soprano capo Ralph Cifaretto. It was Ralph's bad influence, coupled with laziness and a sense of entitlement due to his family name, that propelled Jackie, Jr. into a brief and ignominious career in organized crime.Working alongside his friend Dino Zerilli he began small by selling Ecstacy to college kids. They often hung out at the Ooh Fa pizza restaurant which brought them into contact with Christopher Moltisanti. Jackie planned the robbery of a Jewel concert at Rutgers and drove the getaway car for Christopher and Benny Fazio. Later Jackie tried to use his 'influence' with Christopher to help a drug dealer associate from college named Matush sell ecstacy at the Crazy Horse club, owned by Christopher and Furio Giunta and fronted by Adriana La Cerva. Matush had been thrown out of the club by Giunta once already and Jackie met with him at a "sit-down" and agreed to take his case up with Chris; Chris refused to grant any favours but Jackie told Matush it would be alright to work outside the club anyway - resulting in a severe beating for Matush.Jackie, Jr.'s budding relationship with Meadow Soprano put him at odds with her father and DiMeo family street boss Tony Soprano, and as a result, he tried to maintain the appearance of a respectable college student while drifting further and further into the family business. Tony's interest was further increased because he had been a close friend of Jackie's father and had promised to keep him away from their way of life. Tony began to see through Jackie's facade when he caught him at the casino on Bloomfield Ave and later at the Bada Bing.Things came to a head after Jackie, Jr. flunked out of Rutgers University. Tony was furious because he had tried so hard to keep Jackie straight, beating him up in the bathroom of a rival strip club when he caught him there with another stripper. Jackie was subsequently dumped by Meadow after she found him cheating on her. Resentful of two generations of the Sopranos--the Royal Family, as Ralph mockingly called them--Jackie began working directly for Ralph, forming his own minor crew in the process.Upon hearing Ralph tell the story of when Jackie Aprile, Sr. and Tony took down a card game held by Feech La Manna, Jackie became inspired to follow in his father's footsteps. Using his dim-witted crew of Carlo Renzi, Dino Zerilli and Matush, Jackie attempted to hold up a card game run by Aprile soldier Eugene Pontecorvo. The young, would be stick-up men got high and Jackie almost decided not to go through with it. Once inside things went horribly awry - Jackie killed Sunshine the dealer, Renzi was killed at the scene, made man Furio Giunta was shot in the leg and Matush fled in the getaway car on hearing the gunshots. Jackie, Jr. barely escaped with his life by performing a quick carjacking. He drove straight past Dino Zerilli leaving him to perish at the hands of Christopher Moltisanti and Albert Barese.
