Throughout the series, money seems to be the driving factor for many of the characters, be it legit folks or guys in the "Family".

One thing I notice is the inconsistency in the incomes, one minute they are able to buy diamonds, expensive trips, cars, place heavy bets, and in the next minute are bickering over something like a $1200 restaurant bill.

So let's investigate:

Tony - Possibly broke by the end of the series as his top earners were all dead and suffered from a debilitating gambling problem.
Jackie Sr - Possibly broke as Rosalie mentioned there was nothing left after the funeral
Junior Soprano - Very broke as he had no money left after years of trials and lawyer fees and ended up in a state asylum.
Paulie - Always broke and resorted to robbing old ladies to make his kick-ups to Tony
Silvio - Will be broke due to the hospital stay
Vito - Became broke as he was outed
Carlo, Patsy, Ray Curto - Always had problems earning
Johnny Sac - Assets frozen or seized by the Feds. Died broke and penniless. His wife had to move in with her daughter
Big Pussy - Left Angie with scraps and she ended up selling Kielbasa samples at the supermarket.


I mean, is all this risk of having your loved ones potentially murdered, receiving long prison terms, or getting shot/stabbed really worth it? The guys I mentioned were top earners based on the show's dialogue.