A man named Kerry Packer is perhaps the greatest of these of all time.
Kerry Packer was an Australian business tycoon worth about $6 billion before he died in 2005. During his life, he was known for a lot of things but mostly for his legendary gambling habit. He would phone ahead to a casino to find out how much he could gamble. If he didn’t like the number, he kept hunting til he found what he wanted. On a few occasions, he even ran casinos out of business by winning too much money. He once flipped a coin for $150 million. He won.
Kerry was also a big tipper… he would frequently pay off waitresses’ mortgages. Kerry once made a casino manager fire his waitress so he could tip her $80,000 tax-free. He then insisted she be re-hired. When he had a heart attack, at a casino, he tipped the paramedics each a million dollars for saving his life.