My Friday column suggested that President Trump might want to cool it with all the references to Al Capone, who famously went to prison for tax evasion when the feds couldn’t get him on more serious crimes.

NRA spokeswoman Dana Loesch has also recently complained that the same fate may befall Trump, apparently not realizing that a notoriously murderous Chicago gangster may not exactly be the most sympathetic comparison for our current president. As New York magazine’s Jonathan Chait cheekily points out, Trump and his defenders seem to be relying on the (fictional) legal principle that, for both Capone and Trump, “A person can only be charged with their worst crime.”

Tax historian Joseph J. Thorndike wrote a recent article for Tax Notes about Capone, incidentally, that includes some resonant details about the early 20th-century bootlegger. One is that apparently Capone’s lawyers also argued that it was somehow unfair to convict someone for a tax crime when other bigger charges couldn’t be made to stick.

From a 2011 history by law professor Douglas Linder, also quoted by Thorndike:

In his summation for the defense, Albert Fink told the jury to stand as a bulwark against an oppressive government that was just using the tax law ‘as a means to stow Al Capone away.’… Michael Ahern, summing second for the defense, returned to the theme of an oppressive government bent on using questionable means to put Capone in jail to satisfy the newspapers and the persecutors. “You, gentlemen,” he told the jury, “are the last barrier between the defendant and the encroachment and perversion of the government and the law in this case.”

Thorndike also notes that Capone’s downfall came in part because he initially hired an incompetent lawyer who handed over incriminating information to the feds.

In what became known as the “Mattingly letter,” tax attorney Lawrence Mattingly gave Treasury officials a letter acknowledging that his client had substantial income for 1925-1928, despite Capone previously telling a Treasury agent that he “never had much of an income.”

The Mattingly letter also explained Capone’s central role in his syndicate. Capone’s defense attorneys later tried (unsuccessfully) to suppress the letter during the trial, arguing that “a lawyer cannot confess for his client.”

Linder shares some other bits of color from the defense attorneys’ closing statements. Ahern told the jury that the prosecution had spent far too much money trying to put his client behind bars:

By the same token, when the United States Government reaches to all parts of the country for witnesses, spending large sums in this manner, the government is guilty of acts of profligacy. Far better for the government in these hard times to spend this money for soup kitchens!

Fink argued for his client’s innocence by invoking Capone’s generosity and many loyal, loving followers:

Capone is the kind of man who never fails a friend. He was loved by his followers. Open-handed, generous, a man a bookmaker would trust with a ten-thousand-dollar bet. This does not fit in with the government’s picture of a miserly effort to evade income tax. A tinhorn or a piker might try to defraud the government, but not Alphonse Capone.

And finally, the trial included some evidence that may remind readers of the Manafort prosecution, which is of course what led Trump to invoke Capone’s name in the first place. At one point investigator Frank Wilson produced a list of extravagant expenses that suggested Capone’s lifestyle was more lavish than his claimed income would allow. No ostrich jacket, alas, but the list did include:

$8,000 worth of diamond belt buckles, a $6,500 meat bill, $27 shirts, furnishings bought on a spending spree for his home — all told, “$116,000 that is not deductible from his income,” Wilson said [at trial]. “And yet counsel comes here and argues to you that the man has no income!”

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