9. Charles Barkley: Gambling
Oscar Wilde said it: “moderation in all things, including moderation”. Basketball star Charles Barkley, never got the memo saying “gambling in moderation”. Some forms of gambling are relatively harmless. A few dollars here or there on a baseball game or a fantasy football pool will never hurt someone, but betting the house, spouse or kids on whether or not team X will beat the spread is wherein lies the problem.
Barkley has lost, by his own estimate, around $30 million gambling. The crazy thing is, he still enjoys it as a hobby and doesn’t sound like he regrets the losses. What a problem to have, right?
8. Willie Nelson: Taxes
Legendary country singer Willie Nelson is no fan of the man, man. He never made a secret about it and continues to be an anti-authoritarian figure to this day. Back in the early 90’s, the IRS took nearly everything he had after he was discovered to have not paid taxes or severely underpaid for many years. He ultimately paid all of his debts off in the next couple of years, and sued his former money managers for keeping his money in illegal types of accounts, which was partially what he got in trouble with in the first place.
He released an album called IRS Blues: Who Will Buy My Memories? and sent all of the profits to the IRS. The moral of this story can be summed up in a few sentences. Just pay the damn government when the time comes, or don’t get caught. Furthermore, if you don’t like paying taxes, vote for a small government candidate and hope they win, because illegal tax shelters and just not paying taxes doesn’t work forever.
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