Richie Aprile, the older brother of acting DiMeo Crime Family boss Jackie Aprile, Sr., was a capo in the DiMeo crime family before being sent to prison for ten years. While Richie was in prison, Jackie Aprile Sr died and upon his release, Richie came back to a very different family with Tony Soprano in charge. Richie had known Tony since before he became a made man; Tony himself recalled having to pay for dinners for Richie and others as a newly made man. While Tony and Richie had gotten along in the old days — Richie intervened on Tony and Jackie's behalf when old-school mobster Feech La Manna wanted them killed for robbing his card game — there was no love lost between the two once Richie came back on the scene. Impetuous and irascible, Richie still saw Tony as his younger brother's friend, and subsequently had difficulty accepting orders from someone he viewed as a "youngster". Richie was arguably the most ruthless of the entire mafioso cast in the series.
Tensions between the two developed throughout Season Two. One of Richie's first actions as a free man was to confront his old partner Peter "Beansie" Gaeta and try to claim money from him. When Beansie failed to pay Richie at his welcome back party, Richie tracked him down again and threatened to shoot him. Later, Richie waited for Beansie by his car, and when he went to get in, Richie ran him over twice, paralyzing him from the waist down. Richie was later ordered by Tony to make amends by building Beansie a ramp for his wheelchair, to which Richie said "I'll build a ramp to your ass, run a Lionel up in there."
Richie loaned money to Tony's childhood friend Davey Scatino and eventually cut him off when Scatino started to miss payments. Scatino managed to get a seat at Tony's high stakes executive game and when Richie found him there he flew into a rage. Tony intervened because he could not lose face by allowing one of his players to be harmed and sent Richie away. After the game, Scatino was so heavily indebted to Tony and Richie that both men took over Scatino's sporting goods store, Ramsey Sports and Outdoor, in what became known as "The Scatino Bust-Out".
Richie disliked Tony's protégé Christopher Moltisanti because of his violent relationship with Richie's niece, Adriana La Cerva. Richie once called Christopher a "camel-nosed fuck" . This friction between them contributed to a failed attempt on Christopher's life by two young associates, Matthew Bevilacqua and Sean Gismonte, hoping to impress Richie. Richie had nothing to do with planning the hit and refused to help them afterwards because he expected a reaction from Tony.
Richie acted as a mentor to his nephew, Jackie Aprile, Jr. for a short time before his death; he brought him along to meetings to discuss mafia business.
In the end, Richie was preparing, with the approval of Tony's Uncle Junior, to take over the family as boss. Richie approached acting capo Albert "Ally Boy" Barese to ask for his support in his takeover bid but he declined. After weighing his options, Junior realized he was better off with Tony in charge and tipped him off about Richie's plans. Tony ordered Silvio Dante to have Richie hit for insubordination and plotting to have Tony whacked for interfering in his drug dealing.
Richie and Janice Soprano, Tony's sister, used to date in high school. When Richie left prison, he and Janice resumed their old relationship and eventually became engaged. Janice frequently encouraged Richie to defy Tony, because she wanted to be married to the boss. One night, Richie and Janice were having sex on the couch. In this scene, Richie held a gun to Janice's head during intercourse as Janice found to be a turn-on (a fact she later relayed to Carmela). This particular encounter ended abruptly when Janice said "Oh baby, you're the boss… it should be you." Richie became upset, and told Janice he needed to be loyal. Janice's response "Tell that to Paul Castellano," a reference to the real life slaying of the Gambino boss by John Gotti.
After returning home one night, Richie and Janice entered into an argument over Richie's son's sexuality, an idea Janice dismissed, but defended regardless. As soon as she did this however, Richie punched Janice in the face before settling down for dinner. Appearing in complete shock, after Richie said "What? You gonna cry now?," Janice left the room but quickly returned with a gun and shot Richie in the chest. As Richie in disbelief slowly struggled to crawl away, Janice shot him in the head, killing him instantly. A distraught Janice called her brother Tony who had Chris and Furio Giunta dispose of Richie's corpse by dismemberment at Satriale's Pork Store, and sent Janice off to Seattle to lay low. Apart from Tony and Janice, only Christopher and Furio know what really happened to Richie. Carmela knows of Richie's death, but doesn't know the specifics; everyone else has been told that he became an FBI informant and entered witness protection. He is based on real life Bonanno crime family capo Carmine Galante who in 1979 after his release from prison attempted to take over the Bonanno crime family by murdering Phillip Rastelli. The attempt failed and Galante was later murdered.