Navin Johnson.
Every once in a while he’d come into the bar I worked at.
He’d be with some jerk who’d walk around and goad everyone to “buy the champ a drink” and of course he’d want one too.
Often he could barely stand and some other drunk jerk would try to fight him just to say he took on the champ.
Heartbreaking doesn’t begin to describe it.
These days, what determines if you’re rich or if you’re broke isn’t assets vs. liabilities; it’s cash flow vs. debts come due. In principle, you can owe millions and yet live like a king until the day you die, if you can only structure your debt properly.
John Sutter owned vast landholdings in Northern California – I’ve read his stake reached from San Francisco to Sacramento – and had hundreds of people working for him when gold was discovered on his land. The gold rush destroyed him. He wasn’t quite penniless when he died; I believe he received some sort of pension or stipend in his old age.
Sorry for the double nitpick, but you both misspelled his name. Or rather he misspelled it and you mis-misspelled it.
He never went broke- he still had a thermos and a story.
That guy, don’t you remember? You called him Al. It was Al all the time.
Jimmy the Greek.
July Garland and Oscar Wilde, although I’m not sure how extremely rich they ever were.
Certainly not Jimmy the Greek extremely rich. 
No, that was another of Richardson’s problems, namely, not being able to spell his own first name correctly.
As a prediction for athletes with trouble to come, it would not be at all surprising to see Jamarcus Russell show up on this list, though according to Wiki he’s apparently making some current moves that show slight flashes of sanity, and apparently the NFL has not completely written him off in spite of the very intensity with which he burned his bridge.
Really? I thought it was Barzini all along.
I remembered another author for this category: Dr. Benjamin Spock. Dr. Spock’s Baby & Child Care and his other books sold more than 50 million of copies making him easily on the short list of highest earning authors of the 20th century. He died almost penniless and deeply in debt.
His fortunes began to decline in 1976 when he was 73 and divorced his wife of 47 years. In addition to the fact that everything they had was community property she was a major contributor and editor to his works and he was leaving her for a woman 40 years his junior, thus she received the lions share of assets and the book. Next he had a tax debt that took years to sort out, and he continued to live very well and be overly generous, and then he lived into his 90s and had major medical problems that cost more than his income. His around the clock home healthcare cost $16,000 per month (this was from his obituary) while his income was less than half that and his wife refused to put him in a nursing home which would have been much cheaper, instead appealing- in the newspapers- to wealthy benefactors to please help support him in his final days. (I’m assuming that like Sammy Davis, Jr., the dust eventually settled and left her in better circumstances, but I don’t know this.)
Groucho Marx was well-to-do when he died but not stinking rich by any means, just a “moderate millionaire”. He was one of the highest paid entertainers in the world in his prime but like Mark Twain he wanted to have Bob Hope/Oprah/Paul McCartney money instead of “really really good money”. He lost a fortune in the Depression and then more fortunes in later bad business deals then two divorces in ten years wiped him out; he remained with You Bet Your Life strictly because he needed the money.
In the infamous sordid legal battles twixt his family and Erin Fleming that filled his last days and continued well after his death one of their allegations was that she embezzled from him and forced him to work, but it was revealed that had she not forced him to work he would have been far less comfortable in his final years as his fat personal appearance checks and guest star fees largely replenished his fortune that had been depleted by multiple alimony payments and financial mismanagement. (That was an odd relationship that it’s still hard to determine whether it was May-December love or Elderabuse as there were elements of both.)
John Wayne is another star who was well to do but nowhere near as rich as you might think. His big fortune killers came from divorces and from bankrolling some of his own works, most famously The Alamo which lost him millions.
I’m sure I’m forgetting a stack of others but one that springs to mind is Evalyn Walsh McLean, former owner of the Hope Diamond. At one time rich enough,thanks to her inherited mining fortune and her husband’s newspaper business, to be able to put the famed diamond around the neck of the family dog and let it run around for laughs. Er, that is the dog ran about not the diamond. There was nothing left of the fortune when she died. I read somewhere a tale of the people who bought her home eagerly searching the floorboards in case a spare nugget of gold had been tossed aside, relic from more wealthy and careless times. They were disappointed.
1920s child actress “Baby Peggy” Montgomery (who will be 92 later this month) made a lot of money but lost in, through high spending and bad advice.
The wiki article doesn’t mention it but her maternal grandmother had divorced her husband and married his brother. Her father Jack mostly couldn’t stand step-dad and left home at a young age to be a cowboy, his childhood dream since meeting Buffalo Bill Cody. Later, when his daughter just happened to become a film star (he was in California as a cowboy, part time extra, his wife took Peggy with a friend to get her check and a director saw her and cast her opposite Brownie, the Wonder Dog, who died shortly thereafter). Jack decided to mend fences and bring in step-dad, a banker, to run the finances. Step dad embezzled the money, left his wife for another woman and moved to-where else- Texas to better keep his ill gotten gains.
It may not be quite the same but some Roman emperors such as Caligula and Nero bankrupted the state, or came close to it. Always a bad idea in ancient Rome to give power to some wet behind the ears youth.
Not quite sure how rich she was but Emma Lady Hamilton (Horatio Nelson’s mistress) ended up in debtor’s prison. England decided to honor Nelson’s brother instead of the woman he wanted them to.
Things to avoid if you want to keep your millions:
[ul]
[li]gambling[/li][li]mansions with high upkeep[/li][li]alcohol and drugs[/li][li]ex-wives[/li][li]crooked/incompetent business managers[/li][li]shorting the IRS[/li][li]investing in ventures you aren’t an expert in[/li][/ul]
I’m surprised that no one has yet mentioned Jack Whittaker, the West Virginia man who won the world’s biggest solo lottery prize in 2002 and was in financial ruin barely three years later. His story has it all. Walking around with big wads of cash, which, as you’d expect, prompted an attempted robbery. Heavy gambling leading to massive losses that he couldn’t pay. Relatives going on drugs and ending up dead. Multiple lawsuits. Strippers and strip clubs. Reading the story will make you glad that you never received a three-hundred-million-dollar windfall.
This story reminded me of Viv Nicholson, the 1960s Football Pools winner who famously announced she was going to ‘spend, spend, spend’. Which she did, falling rapidly into financial difficulties and things spiralling out of control, as this little snipprt from the wikipedia article illustrates:
Still, on the upside, she DID get to feature on the cover of a single by The Smiths.
Ex-wives played a part as well.
I used to fancy myself something of a John Wayne expert, but I had no idea how less-than-solid his financial situation was until about ten years ago. He kept up a very grueling workrate over his entire career (up until the last five years or so of his life) despite having major surgery for cancer that cost him a lung and four ribs. I always thought this was just part of his work ethic and desire to make movies, since I’d read a blurb that he’d made a fortune in Arizona/New Mexico real estate. Come to find out he kept up his schedule (including starring in some real clinkers) because he really needed the money.
I’m not sure he really belongs in this thread, since we’re talking about a man who kept rooms in several hotels around the country and practically lived on his massive yacht, but he was never comfortable enough to kick back and retire until his health made it impossible to do anything else.