After having been forced pay taxes on a PT Cruiser he won in a raffle in 2007, Sherman W. Friend of Pennsylvania vowed never to pay taxes on winnings again.
In 2009 he drove to West Virginia to play slot machines so his winnings will not be easily tracked. When his slot machine adventure netted him $1600, his next move was to buy 208 fifty-cent lottery tickets using the same lucky number.
When the tickets returned $520,000 in winnings, Sherman asked forty mostly unemployed and destitute people to cash in the tickets for him, paying each about $250 per ticket.
When the IRS found out, it sued Sherman who was recently sentenced to 1 year in jail, $3000 in fines and $132,445 in back taxes, penalties and interest.
Read more in http://www.cpapracticeadvisor.com/news/10944461/71-year-old-lottery-winner-gets-1-year-in-prison-for-strange-tax-evasion-scheme