Son of the Mob

Son of the Mob is a two-book series by Gordon Korman, detailing the life of Vince Luca, a boy whose dad Anthony Luca is the head of one of the biggest east-coast crime familes ever. Vince, on the other hand, is a law-abiding citizen, and tries to stay out of his dad's work however he can (especially since his Love Interest is the daughter of the FBI agent tasked with investigating his family).

Contains examples of:

 * The Ace: Patrick (P-Rick), also being Always Someone Better for Vince's film class in the second book. He does turn out to be a good person, if overly serious about his art, when he convinces Kendra to talk to Vince instead of making assumptions.
 * Beware the Nice Ones: Vince's mom. . Don't mess with an Italian mother.
 * Mafia Princess: Vince is the male version and the reluctant version. He also gets more slack than his older brother, Tommy, since he doesn't want anything to do with the business and the family tries to keep it that way (unless necessary).
 * Vince is constantly torn between doing the right thing and loyalty to his family, which drives several aspects of the plots of both books.
 * Parental Favoritism: While Anthony and Mrs. Luca love both their boys very much, Anthony clearly wants Vince to be the one to take over the family business since Tommy only thinks in the short-term and is generally unmotivated. However, so far Tommy is the only one to show interest in the "vending machine business" (even though by the end of book one, Vince has shown a better aptitude for manipulating it).
 * Riding into the Sunrise: Vince's movie script from the beginning of book two describes him, Kendra, and Alex doing this as they make the cross-country trip to their college, but Kendra points out that that would be impossible since they're going west.
 * Star Crossed Lovers: An example of the Romeo and Juliet comparison being done right: Vince is dating Kendra Bightly, whose father is the head of the investigative team who deals with the Luca family. Both Vince and Kendra were terrified when their parents (more accurately, their fathers) met at their graduation, but there was just a tense handshake and a terse greeting. Both have acknowledged that this is the best that they can hope for.
 * To Be Lawful or Good: Vince refuses to make the choice, avoiding any situations that would prompt it. The first book's moral is that there's no way for him to do this unless he cuts all ties to his family, because only when he's away from them will he have no opportunity to protect them from the consequences of their own actions. (See Beware the Nice Ones--Vince actually approves, but he can't do something like that, and the guilt from not doing it if he had the chance would tear him apart.)
 * Well Done Son Guy: Tommy shows shades of becoming this, because he seems to know that Vince is acknowledged by everyone as being smarter than him. However, Anthony always tries to show that he loves both his sons.
 * Youngest Child Wins: Vince is shown to be more motivated, smarter, and more-liked by the family than his older brother Tommy. Also, despite Tommy actually wanting to be in the Family Business, Vince has shown more aptitude for doing what a mob boss would do (even if he did it to save Jimmy Rat, a sort-of friend).
 * Your Costume Needs Work: In Vince's video of, his teacher declares everything perfect except for Anthony, who was clearly "a caricature" of a mob boss. Vince tries not to laugh.