Tony’s first major operation with the mob came when he joined Jackie Aprila and two other associates to rob a card game. This act became a legend among the mob and formed a lasting friendship between Tony and Jackie.
As Jackie nears the end of his life, he tries to keep his son Jackie Jr. from illegal activities, feeling that he just doesn’t have the guts to do so. After Jackie’s death, Tony vows to keep his friend’s son out of the business.
Despite this, Tony never aspires to be Jackie Jr.’s mentor, instead leaving it up to Jackie Jr.’s uncle Richie, who leads him into petty mafia activities. This doesn’t last long because Tony’s sister kills Richie during an argument. Jackie Jr. is then taken under the tutelage of an even worse mentor: Ralph. As Jackie Jr. searches for the father figure, Ralph tells him a famous story about Tony and his father looting a card game, which inspires him to do the same.
There’s no denying that Tony is trying to steer Jackie Jr. in the right direction, especially when he starts dating Meadow. Tony recognizes himself in Jackie Jr. and wishes he would escape this world. But when it really matters, and Jackie Jr.’s Tony-inspired card game goes awry, Tony doesn’t even think about protecting Jackie Jr.
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