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Ill Gotten Gains

The Supreme Court of the United States views the privilege against forced self-incrimination – commonly referred to as the right to remain silent – as a flexible right. It has ever been thus. For anyone who harbors fantasies about a halcyon time in American history when the Supreme Court was a bastion of freedom and individual liberties as enforced against an overbearing state, you are sadly mistaken. There has never been such a time. While there have been outstanding members of the Court throughout history, and there have certainly been some fruitful decisions, overall the Court has always been awful.


Well, maybe awful is too strong a word – it has always had an agenda. And, the early 20th Century proved a very interesting moment for the Court. As many know, it had an, umm, interesting view of the Reconstruction Amendments depleting most of their promise for a more equal and fair nation. And then, the Constitution changed quite a bit more. Of the 27 Amendments to the United States Constitution, 10 of which hardly count because they came on the heels of ratification, 6 would come between 1865 and 1919. The 16th Amendment granted Congress the power to collect income taxes “from whatever source derived” in February, 1913. Later that same year, the 17th Amendment granted citizens the power to elect their own United States Senators directly. Just a few years later, in 1919, the 18th Amendment prohibited manufacturing, selling, or transporting alcohol. These Constitutional changes radically altered the relationship Americans had with the federal government and with the powers the federal government could – and would – exercise.


A particular United States Assistant Attorney General, Mabel Walker Willebrandt, pioneered a prosecution theory for tax evasion under the 16th Amendment to ensure that the federal government obtained the income tax it was due by seeking tax from income derived from activities prohibited by the 18th Amendment. This would present a problem, however, because by admitting the income from unlawful acts, the taxpayer would, necessarily, be in a right-to-remain-silent-pickle. If he admitted the income from manufacturing, selling, or transporting alcohol, he would be incriminating himself as a violator of the laws prohibiting doing those things. Surely, the Supreme Court of the United States would protect the sanctity of the 5th Amendment privilege over enforcement of prohibition, right? Wrong.


In United States v. Sullivan, 274 U.S. 259, 263 (1927), the Court declared, “We see no reason … why the fact that a business is unlawful should exempt it from paying the taxes that if lawful it would have to pay.” The argument leading to that ruling was pioneered by Mabel Willebrandt.


Mabel Walker Willebrandt rabbit hole: In a word, she was brilliant. Willebrandt taught school full time while she attended law school. In that same moment, she volunteered her services as an unpaid public defender in the “police courts” where she was listed as counsel in over 2000 cases, mostly defending women accused of prostitution. During WWI, she headed the Los Angeles Legal Advisory Board for conscription cases. She was not even 30. And incredibly impressive. In 1921, every single judge in Southern California recommended her for a position as Assistant Attorney General in the Harding Administration. She claimed to be personally opposed to Prohibition, but she campaigned for “dry” candidates and enforced the Volstead Act with ferocity. She prosecuted South Carolina bootlegger Manly Sullivan for failing to file income taxes despite having earned income (from criminal activity). Indeed, she argued over 40 cases before the Supreme Court, winning major victories. For reasons known only to him, President Hoover did not take the opportunity to appoint the first woman Attorney General when he came into power and - to her credit – Mabel resigned when she was passed over. One may not agree with her politics but Mabel Walker Willebrandt had a keen legal mind and was an exceptional lawyer.

The Sullivan ruling opened the door for the federal government to engage in a lot more crime fighting. Turns out that trying to stop the new violence associated with the formerly peaceful supply of alcohol to a population that desperately wanted it became an industry unto itself. Local governments were not prepared for the crime wave Prohibition initiated and begged the federal government to step in. No one begged more than the folks in Chicago. They wanted the notorious Al Capone off their streets. Willebrandt's theory of requiring the declaration of ill gotten gains for tax purposes would be the ticket. Interestingly, Capone’s brother was convicted for tax evasion prompting Al to call his lawyer and arrange for his own income to be declared. That was not done. But, what did happen is that the lawyer admitted certain income to the federal government on which Capone would be willing to pay taxes (in other words, his lawyer was trying to open a negotiation). This saved the government the burden of doing any work at all save calling together a grand jury to indict Capone, which they did to the tune of dozens of charges – years of income tax evasion and thousands of violations of the Volstead Act.


Capone’s lawyer and the feds agreed on a plea deal, but the judge refused it and left the lawyers with little time to prepare for a trial. With mounds of evidence against their client, this must have been a nightmare for counsel. Despite what anyone may think about Capone and his business practices, that trial was incredibly unfair. It was almost a kangaroo court - conviction was guaranteed. Capone was sentenced to 11 years in prison on October 17, 1931. Even though he had a lengthy career, he was only 33 years old. When he arrived in prison, he was frail and already suffering from symptoms of syphilis. Seven years into his sentence, he was granted parole due to his poor health and severe mental deterioration. He would live another ten years or so and actually be one of the first people treated with penicillin which slowed, but did not cure, the effects of his illness. He died at the age of 48. It’s unclear if he ever paid the taxes.


Maybe the moral of the story is that if local governments find you to be a nuisance and state governments want to run you out of town because your antics are just more than they are prepared to manage (even if you helped to get all of those folks elected) and the federal government has tools to prosecute you (even if they present you with the Hobson’s Choice of self-incrimination for illegal activities or prosecution for tax evasion), they will find you and throw the proverbial book at you. And, if you think the Supreme Court will save you, think again.



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