At the end of season 6, Tony was complaining about heating the pool and ran into big money problems which caused him to reach into his own stash to make up for the gambling losses. Carm's Dad built Tony's house, so maybe it was a gift/present for him. Vito and Ralphie were long gone at that point, so his cushion of easy money was gone. AJ's mental asylum stay was 2K a day in which Tony pissed and moaned about.

Rosalie openly admitted to money problems after Jackie Sr. died, but she could have gotten some type of death benefit once her husband passed on.

Sil wasn't a Boss, he did well, but who is running the Bing in his absence? Probably no one close to his bookkeeping acumen. Paulie maybe? Imagine how much a hospital stay for comatose patient would run you?

Paulie constantly had money woes and often complained about his Mother an the retirement community which was 8K a month. Towards the end he nearly fought Chris over a measly 1200 restaurant bill.

Junior went broke or in the process of going to the poorhouse once his plot to take out Tony failed and he lost much of his territory and power. Once the RICO trial started, he was getting fleeced royally by his lawyers with their appeals, discovery evidence, and "Wrigley Fuckin' Field" invoices. Remember when his Lawyer casually mentioned a basic analysis of Wiretap info would run him 400K? That is only what we saw of his fees. 6 years of that on a reduced earnings would drive him literally into the poorhouse. We always saw Junior begging Tony for more points so he could pay for his medical bills....Oh, right, yeah, the out-of-pocket medical bills with the Cancer....Junior had no money.....


Bobby couldn't even afford to help with Uncle June staying in the retirement center.

In the Episode "Chasing It", Jenny had to move in with Allegra because the Feds left her with nothing....80-85% of his assets which was 6 million which leaves 1.2 mil left for Jenny....whoa, lest not forget the wedding, which was 500K...700K left, then taxes, lawyers, fees, Sallie Mae Loans, yeah, John was toast. He tried to liquidate some assets (like the property in New Orleans), but fell through. The fact that he had to trust a man in another Family and not Philly showed how desperate the situation was for him.

If Vito was so rich, Marie wouldn't have begged Tony for a 100K to move to a new location. If anything she could have put the house up for sale and got out of there.

Rats, War With NY, Murder, and Tony's bad decisions certainly brought an end to financial prosperity.