Raised in comfort, it was easy for a young Anthony to assume himself deserving of the things he had been provided. As a sheltered child sometimes is, he was near unaware of other states of being until he was old enough for school.
School that taught the young boy about injustices, and how hard many people had to fight in order to find themselves in anything resembling the life he had.
So he vowed to fight just as hard to stay ahead- not difficult when hand-me-down funds roll in.
In order to preserve this wealth for future generations, he involved himself deeply in the stock market as he aged. A gradual build to a point where the earnings alone were enough to live on. After complications when his assistants made off with withdrawal slips and skipped town, perhaps even the country, he was left with a fraction of the wealth left, and no motivation left in his heart to relive all he'd built over time.
Rather, he had a compulsion to fight from the bottom. Without other skills and no means to coast on inheritance, Anthony was exactly driven and morally rotten enough to fit in with the mafia. Turns out that things accumulate much easier in the family.
It can be difficult to get a read on just how far exactly the man would go in order to find success where he is now.