Joe Louis Heavyweight boxer and longtime world champion Louis was both overly generous and swindled by his handlers throughout his career. Despite earning $4.6 million in winnings over his lifetime, Louis saw only $800,000 of it. Worse, engaging in charitable fights for the military during WWII landed him in hot water with the IRS that would last for the rest of his life (and beyond). The IRS claimed, despite all the money raised going to charity, that Louis owed taxes on it, a fee that ballooned to more than $1 million with taxes and penalties. Louis also bought homes, cars, and schooling for his parents and siblings, and paid back the government for any welfare funds they'd received. To pay his enormous tax bill, he turned to professional wrestling and repeatedly came out of retirement to box — with diminishing results. Ultimately, former rival Max Schmeling and mobster Frank Lucas (who was disgusted with how the government had treated Louis) provided financial help, and the IRS agreed to limit its collections to amounts based on his post-retirement income. Though he was broke, these dual donations allowed him to live comfortably until he died of a heart attack at age 66 in 1981.
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