Brian Galle, a tax professor at Georgetown Law School, has this article: Trump’s Bookkeeper: How Prosecutors Could Easily Prove Tax Crimes for Hush Money Reimbursements (Just Security 12/18/18), here.
Brian's article links this article by Martin Sheil, former Supervisory Special Agent IRS Criminal Investigation: Did Trump Organization Executives Cook the Books?–Tax Crimes Explained under Federal and State Law (Just Security 12/18/18), here.
Both are good reading, although written for readers who are not tax crimes specialists (who do need to reminded from time to time about Cheek).
Here is a good excerpt from Brian's article:
In my view, Trump’s key defense to the campaign finance charge would focus on his purpose in making the payments. There’s a strong circumstantial case to be made that candidate Trump knew secret mistress payoffs could be crimes: he tweeted about the John Edwards prosecution for the same general sort of conduct, and was broadcast saying he had talked to lawyers after reading about that case. So his best shot is to say simply that he paid not to influence the election, but instead for personal reasons, such as to avoid hurting his wife. The timing, in October of 2016, makes that argument challenging, but he might say that he knew the timing would drive press coverage that would be especially hurtful or that it was his accusers who dictated the timing.
But down that road lies tax fraud. The problem is that if the payments were indeed personal, they were not deductible business expenses. In all likelihood, when Weisselberg created an account entry listing the payments as “legal expenses” for the Trump Organization, that entry resulted in those costs being deducted from the Organization’s income (as with many things Trump, it would of course be useful to see the tax returns themselves). Although Trump probably no longer signs the Organization’s tax returns, and so likely did not himself lie on the 2016 return, he could be guilty of conspiring with others to fraudulently reduce the Organization’s taxes. The payments likely also should have been taxed to Trump personally as de facto distributions of profits; whether they are reported as such on his personal tax returns is also an interesting question for investigators.
Just as with the campaign offenses, mental state is critical to tax offenses, and so it is here that Weisselberg will be critical. Ignorance of the law actually is an excuse for tax crimes. Because the tax code is so complex, taxpayers can’t be convicted of most tax offenses unless they undertake a “voluntary, intentional violation of a known legal duty.” Cheek v. U.S., 498 U.S. 192, 201 (1991). Proving that defendants actually knew what they were doing was wrong is the most challenging part of almost any tax prosecution.
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