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Average Salary: $50,000,000

Expected Lifetime Earnings: $1,000,000,000

Being a lowly soldier in a crime family means you're making money only when the boss decides you've earned it; it's the status and possibility for advancement that keeps you in it, not the money.

Start paying up or we start knocking them down. (Source)

That all changes when you finally kill enough peo—er, work hard enough to become the mob boss. Just like any CEO or store manager, you take more risks, you have more responsibilities, and you probably work longer hours. 

You're getting a cut of all the businesses you're involved in, which can be incredibly diverse depending on your attitude and motivation. Gambling, extortion, drug trafficking, neighborhood "protection" funds, wind energy—whatever gets you those untaxed stacks of cash whenever you or your friends show up.

A mob boss can earn a seemingly unlimited amount of money; after all, making, stealing, blackmailing, and flat-out knocking down old ladies and taking their money is what the mob is all about. But can you, as the boss, display your wealth? 

You may want to do that on the down-low, maybe outside of the city you own. You don't want to give the cops any cause to pick you up, you don't want the I.R.S. on your tail, and you never know which subordinate is going to try to take your job (you should probably just assume all of them).

Good thing you have several houses you can go to at any time. If you're going to be doing illegal stuff, at least diversify your assets so it makes it more difficult for them to find it all.