Regarding Jackie, Jr....this was when it must suck to be in the mob.

Tony has to order the hit of a very close friend's son- Jackie Sr probably asked Tony to keep an eye on his son and watch over him. Or...Ralph has to order the hit of his girlfriend's son. Rosie was barely over grieving for her late husband.

What made it less gut wrenching for the viewers is that Jackie Jr was such a jerk in the show.

You shit-kicking, stinky, horse-manure-smelling motherfucker you! If you ever get out of line over there again, I'll smash your fucking head so hard you won't be able to get that cowboy hat on. You hear me? Fucking hick. -Nicky (Casino)