One thing I will say, because I've spent too much of my life talking to @matt_levine, is that one of the *problems* with our tax evasion laws is that once the government decides to come at you, they WILL get you, because a BUNCH of stuff is technically "tax evasion."
So, like, the question really becomes "do the Feds hate you enough to go after you." Once that answer is *yes*, you're TOAST.

HERE, the Feds never decided to go after Trump (including now, depending on what the SDNY is doing).
If they had, they would have caught him. They'd have caught him long before he ran for president and ruined America and helped kill 200,000 people.

But, remember, that could be said about almost *any* large org they don't like.
The problem, as I'm sure @BernieSanders and @ewarren fans are waiting for me to get to, is that the entire SYSTEM favors the rich committing low-grade tax evasion, AND sucking up to prosecutors who don't think tax evasion is important but use it as a hook if you piss them off.
The SOLUTION, is to close up the distance between tax "avoidance" and tax "evasion." You've got to close up the loopholes that make it easy for the rich to avoid taxes, which also would make it harder to cheat. And then MERCILESLY STRIKE at those who still do.
But closing up all those loopholes is *painful* to the business community, and they fight it with everything they've got.
Put another way, nobody should go to jail for lying about a haircut. But the way to fix that is to NOT HAVE HAIRCUTS be deductible expense EVER.

And that sounds broadly acceptable, but when I say "OR LUNCH" Don Draper comes at me with a sawed off coke bottle.
Uhh... just to be clear, Trump should ABSOLUTELY GO TO JAIL for *apparently* paying $750,000 to his daughter to decrease his taxable income and listing one of his homes as a business to deduct property taxes. That's the egregious stuff.
I just don't care about the haircuts is all
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