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One of the more unusual political memes we've come across presented four different cases of tax-related financial improprieties to suggest that tax-evasion prosecutions were somehow influenced by racial bias against non-blacks: However, the Tax Racism meme offered examples — not all of which were actual cases of tax evasion — so widely spaced in time and so differing in circumstances as to be non-useful in making any point at all about either tax fraud or race. Martha Stewart, the entrepreneur who rose to prominence as the author of books on cooking, entertaining, and decorating, was not charged with, or imprisoned for, non-payment of income taxes. Stewart was found guilty in March 2004 of felony charges of conspiracy, obstruction of an agency proceeding, and making false statements to federal investigators in a case related to a U.S. Securities and Exchange Commission (SEC) investigation into insider trading activity: Stewart was sentenced to 5 months in prison and also settled a civil suit with the SEC by paying a $195,000 fine (a penalty that reflected four times the amount of stock value loss she avoided by taking advantage of inside information, plus interest). Stewart did engage in a dispute with the state of New York in 2002 over unpaid property taxes that she contended she didn't owe because she hardly spent any time in that state, and she was eventually ordered by a judge to pay $220,000 in back taxes plus penalties. But contrary to the false impression created by this meme, she was not prosecuted or jailed over that issue — the time she spent in prison was solely related to a later insider-trading case, not to tax evasion. By the mid-1920s, notorious Chicago mobster Alphonse Gabriel Capone was reportedly taking in nearly $60 million annually ($878 million in 2018 dollars) from a variety of illegal activities, primarily Prohibition-era bootlegging. Capone was dubbed Public Enemy No. 1 after the 1929 Saint Valentine's Day Massacre in which gunmen allegedly hired by him posed as police officers to murder seven members of a rival gang, leading to increased public pressure on the government to rein Capone in. Federal authorities had difficulty gathering sufficient hard evidence to convict Capone on any substantial criminal charges, however, so they took what was then a novel tack: Even if they couldn't prove Capone was making his millions illegally, they could prove he wasn't paying income tax on his ill-gotten gains. Despite his obviously lavish lifestyle, Capone never filed a federal income tax return and claimed he had no taxable income, reportedly boasting at one point that, They can't collect legal taxes from illegal money. He was proved wrong. IRS and Treasury agents gathered evidence that Capone had made millions of dollars in untaxed income, and the mobster was eventually indicted on 22 counts of federal income tax evasion. After conviction he was sentenced in 1931 to 11 years in prison, fined $50,000, and ordered to pay back taxes in the amount of $215,000. Capone was released from prison in 1939 with time off for good behavior and retired to Florida, where he died in 1947 at the relatively young age of 48. In a literal sense Capone was indeed jailed for non-payment of income taxes, but the tax evasion charges were essentially a proxy for prosecuting the mobster over the multitude of vastly worse and violent crimes with which he was connected (and the immense profits he derived from those criminal activities). Capone was by no means an otherwise upright and law-abiding citizen who was thrown in prison simply because he didn't pay his income taxes. At this point in our narrative we need to distinguish between different forms of tax evasion. At one end of the spectrum are those who haven't engaged in any fraudulent behavior but simply didn't or can't pay their taxes for any number of reasons — maybe they didn't plan or withhold prudently, they received poor financial advisement, they had legitimate confusion or dispute over what constituted taxable income, or they simply overspent and ended up in debt. Although non-payment of taxes is a crime, the IRS will not usually seek prosecution in these types of case and will instead work with offenders in order to facilitate payment of their back debts (rather than making repayment difficult or impossible by incarcerating them). At the other end of the spectrum are those who actively engage in fraud in order to evade the full payment of taxes: They fail to disclose their full income, hide financial transactions, claim deductions to which they are not entitled, disguise monies earned as something other than income, or otherwise file falsified tax returns. The IRS will, at their discretion, seek prosecution in egregious cases of these forms of tax evasion. Leona Helmsley, derisively known by the nickname as the Queen of Mean, was a billionaire who — along with her husband, real estate investor and broker Harry Helmsley — owned a vast portfolio of real estate and other assets, including a chain of hotels and the iconic Empire State Building. Leona Helmsley, who once reportedly asserted that We don’t pay taxes. Only the little people pay taxes, fell into the latter class of tax evader, falsely manipulating her personal finances, business expenses, and dealings with third parties in order to avoid paying immense sums of taxes: She was convicted of 33 felony counts related to her evasion of $1.2 million in federal income taxes. She was sentenced to 16 years in prison (reduced to four years on appeal), fined $7.1 million for tax fraud, and ordered to pay some $1.7 million in back federal and state taxes. She began serving her sentence in 1992 and was released from federal prison in Connecticut in 1994 after having served less than half her sentence. Where along the tax-evader spectrum between legitimate dispute and willful tax fraud civil rights activist Al Sharpton might fall is a difficult to determine. Claims were made in the press in 2014 that Sharpton owed some $4.5 million in unpaid taxes, but the accuracy of that number and how much of the monies owed might already have been repaid by Sharpton were unclear, and his tax-troubles narrative involved a muddied mixture of personal, business, and non-profit finances as well liabilities for federal taxes, state taxes, payroll taxes, and personal income taxes. Much of the dispute over the why and how much of Sharpton's unpaid tax bill stemmed from the operations of the National Action Network, a not-for-profit, civil rights organization founded by Sharpton in 1991. Sharpton contended in a 2014 New York Times account that he incurred an unexpected tax liability because he was taxed personally for income he had given to the non-profit organization, and that he was up to date on repayment plans. Officials contested that the amount he was in arrears for in unpaid taxes had actually grown larger, though: Sharpton then contested that news account, asserting that it referenced old taxes and insisting again his tax liens had been paid down below the $4.5 million debt claimed in the New York Times report that stated Sharpton's unpaid tax debt had nonetheless grown larger, not smaller: Regardless of the numbers, Sharpton wasn't put in prison because tax officials did not deem his case to be an exceptional one of scofflaw tax fraud or evasion that merited prosecution, instead working with him to facilitate his paying down the debt. The conclusion here is a simple one: Cherry-picking four very disparate cases of financial wrongdoings spanning several decades, while ignoring the many other instances of tax evasion successfully prosecuted by the U.S. government, documents nothing about any purported racial bias in such prosecutions.
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