April 16, 1922: On this day, Manny Sullivan challenged his 1922 tax evasion conviction for operating a bootleg booze company in violation of the National Prohibition Act, which he was convicted of in 1922. “Manny” was Sullivan’s nickname. Sullivan appealed his conviction because submitting a tax return on the earnings of criminal operations violated his Fifth Amendment protection against self-incrimination. Sullivan claimed that the alcoholic drinks sent to Charleston, SC, were not his. Sullivan won his appeal in the Department of Justice’s Court of Appeals, which ruled that his illegally obtained money was subject to federal taxes. For this reason, he was protected by the Fifth Amendment, which forbids him from paying such taxes. Mabel Willebrandt, an Assistant US Attorney General, tasked with executing federal tax and prohibition laws, filed an appeal with the Supreme Court.

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