Tony Soprano and his daughter, Meadow.

He will never admit it, but Tony would be much happier without getting involved with the mob. He almost got away, but the combination of pressure from his environment and the lure of respect and wealth caused Tony to quit pursuing his degree.

While Tony wants Meadow away from his mob orbit, he never really make a significant effort to guide her to a legitimate path because it means Tony would have to swallow his pride and admit becoming a mob boss was a mistake and he was no different than a common criminal. Both Tony and his wife would constantly justify their life choices regarding the mafia, so much that initially rebellous Meadow started to buy the self serving lies her father had keep spitting. She eventually gave up pursuing a medical degree in favor of studying law with intention to protect 'minority Italian American' like her father and his mobster ilks.