He's a self-described poor little rich boy who was packed off to boarding school at the age of 11, ignored by a string of stepfathers and now lives in a multimillion-dollar Park Avenue apartment with a butler.
Today, at age 83, that rich little boy, Anthony Marshall, the son of New York City's legendary philanthropist Brooke Astor, faces criminal charges for allegedly mishandling his mother's $198 million estate.
The high-spirited doyenne died in August at the age of 105 after suffering from Alzheimer's disease. Her third husband was the son of John Jacob Astor IV, who controlled a fortune in fur, real estate and banking and died aboard the Titanic.
More focused on her social life and charities, and aloof with her son, Astor called him "baby" well into his senior years, according to a recent interview Marshall gave to New York magazine.
Marshall joined the military, dabbled in diplomatic posts and eventually financed theater productions, while his philanthropic mother danced well into her 90s and supported institutions like the New York Public Library and the Metropolitan Museum of Art.
The family war began in 2006 when Marshall's son Philip filed a petition with the court, alleging that his father had "turned a blind eye to [Astor], intentionally and repeatedly ignoring her health, safety, personal and household needs, while enriching himself with millions."
Marshall may be the prototypical example of the wealthy son who is plagued by "affluenza" or "entitlement-itis," according to estate planners for America's richest families.
Having seen the dark side of wealth and worrying that their children will end up troubled ne'er-do-wells, some of today's richest families are asking "how much is too much" to inherit?
"When I deal with clients who are worth $50 million and up, their biggest concern is, 'how do I not screw up the kids?'" said Jeffrey Baskies, a Palm Beach, Fla., lawyer who handles estates and trusts.
"How do I use it as an incentive for kids to grow up to be mature, self-reliant people with some degree of empathy for the world around them and not turn out like Paris Hilton?"
Few things divide families more than money. Stories abound of wastrel children who fight each other or their parents for an expected inheritance. Some turn to substance abuse or suffer from depression.
In 2002, two members of Chicago's Pritiker family, heirs to the $15 billion Hyatt hotel fortune, alleged that other family members had looted their $1 billion trust funds.
Carter Cooper, the son of fashion designer Gloria Vanderbilt (the granddaughter of rail tycoon Cornelius Vanderbilt, whose father died of alcohol poisoning) jumped to his death from a 14th-floor penthouse. One of her other relatives squandered his money and died penniless.
Shell and Chevron heir John Paul Getty III survived a high-profile kidnapping, then went on to suffer a drug overdose-induced stroke that left him paralyzed and vision-impaired.
More recently, Max Factor cosmetic heir Andrew Luster was hunted down in Mexico in 2003, after fleeing in the middle of a trial on rape charges. Paris Hilton, heiress to the hotel chain fortunes, served time in jail on charges of drunken driving earlier this year and has been derided for being famous for doing nothing.