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Contrary to popular belief [1] some bootleggers in the 1920's did pay their federal income tax. As John J. Binder wrotes in *Al Capone's Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition*, pp. 242-3, "not everyone in his shoes refused to pay the government, and he [Al Capone] should have followed that example. In 1923 almost five thousand bootleggers around the country paid income taxes. John Torrio, Hirshie Miller, Maxie Eisen, and Frankie Lake did so in 1924, and it was front-page news Eddie Waters, a zealous internal revenue agent in Chicago, pestered various bootleggers, including Capone's brother Ralph, about filling out their tax returns. He even helped them do it in a way that did not reveal their sources of income. Certainly the federal government had charged several bootlegers with income tax evasion as early as 1925, and in 1927 the US Supreme Court ruled that it was legal for the government to collect come taxes from illegal activities. Robert Schoenberg, for one, is astounded that by 1929 Al Capone did not simply settle up with the government for the previous years' tax liabilities, which would probably have closed the issue."

(The Supreme Court decision Binder refers to is *United States v. Sullivan*, 274 U.S. 259 (1927), https://supreme.justia.com/cases/federal/us/274/259/case.html where Justice Holmes wrote, "We see no reason to doubt the interpretation of the Act, or any reason why the fact that a business is unlawful should exempt it from paying the taxes that, if lawful, it would have to pay. As the defendant's income was taxed, the statute, of course, required a return...In the decision that this was contrary to the Constitution, we are of opinion that the protection of the Fifth Amendment was pressed too far. If the form of return provided called for answers that the defendant was privileged from making, he could have raised the objection in the return, but could not on that account refuse to make any return at all. We are not called on to decide what, if anything, he might have withheld. Most of the items warranted no complaint. It would be an extreme, if not an extravagant, application of the Fifth Amendment to say that it authorized a man to refuse to state the amount of his income because it had been made in crime. But if the defendant desired to test that or any other point, he should have tested it in the return, so that it could be passed upon. He could not draw a conjurer's circle around the whole matter by his own declaration that to write any word upon the government blank would bring him into danger of the law....In this case, the defendant did not even make a declaration, he simply abstained from making a return." In other words, Capone would have to say "I made X million dollars" and pay the taxes on it, though he could not be forced to say that he made the money through bootlegging or running gambling houses or brothels if the answer would incriminate him.)

So suppose Capone had indeed paid his income tax. Here we have to remember one thing: Eliot Nesss and his "Capone squad" AKA the Untouchables, while they no doubt ate into Caponne's profits with their raids, did not "get" Capone; Ness had nothing directly to do with George E. Q. Johnson's indictment of Capone for income tax evasion, which is what actually sent Capone to prison. It is true that, using wiretaps, the Capone squad was able to get an indictment of Capone for bootlegging which could have been used as a back-up in case the tax charges failed. Johnson wisely decided to give the tax rather than the bootlegging charges first priority because jurors in Chicago in the early 1930's were a lot less likely to feel sympathy for income tax evaders than for people who provided liquor for willing customers. If the tax charges had failed--or in this ATL not been available--would the bootlegging charges have succeeded? It is far from clear. Success would have depended on the promised testimony of a number of gangsters who were facing long prison sentences that the man they were referring to in the wiretaps as "the Big Fella" and by other nicknames was in fact Capone. They might have been willing to so testify to get lighter sentences, or they might in fear have backed away--and even if they didn't back away, the jury might choose not to believe them. There's a good discussion of this in Douglas Perry, *Eliot Ness: The Rise and Fall of an American Hero.* https://books.google.com/books?id=6Wg2AAAAQBAJ&pg=PT60

And remember that in 1925 the top income tax rate was reduced to 25 percent (thanks, Andrew Mellon!) so it's not as though the Big Fella would be hurt *that* much financially.

[1] Little Bonaparte: [thick Italian accent] Thank you, fellow opera-lovers. It's been ten years since I elected myself president of dis organization... an' if I say so myself, you made duh right choice. Let's look at duh record: In duh lass fissel year we made a hundred an' twelve million dollars before taxes... only we didn't pay no taxes! http://www.imdb.com/title/tt0053291/quotes
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