No, I just managed investment portfolios for billionaires, including people more wealthy than I'm sure anyone on this site has worked with. I have often and frequently encountered tax work for the extremely wealthy, including things like modeling cascading GRAT's and managing CDIT portfolios, if you even know what that is. So perhaps I'm not quite as ignorant as you'd like to think, and maybe we take step back from the unnecessary jabs on the nuance of tax laws. I let the lawyers do the tax work because, admittedly, it's not my area of expertise, and I understand extremely well, again, as a private banker, the lengths the wealthy take to minimize taxes.
Further, you seem to not be keeping up with the train of thought here, as I'm talking about potential criminal liability. If you're trying to say that a big booster gives one rat's *** about his spoiled grandchildren getting another hundred thousand dollars after he's dead over his beloved football team winning another ring while he's alive, I'd say your logic is highly flawed.
Finally, at no point did I say "only Ned Flanders files tax returns." I said no one files for (or rather claims) every single thing they should file for. That's kind of an enormous difference.
Look, you've always been an arrogant individual who likes to brag about what he does, as if that purchases additional respect or credibility.
All you have to do is look at your "if you even know what that is" line. Yeah, I have an LL.M. in Tax Law. I "know what that is".
But, yeah, you are pretty ignorant. Not just because you don't know things (and CONTINUE to yap as if your "investment banking knowledge" is on point here), but because you continue to sneer at others who are simply trying to provide accurate information to rebut your misstatements.
I don't know how to convince you as to how ridiculous your statements are, so I'm going to stop trying. I'll leave you with a couple of real world realities that show just how misguided your "spoiled grandchildren" nonsense is. First, if you honestly believe that the loss to an estate for non-filing would be only "another hundred thousand dollars", that's your choice. But you're wrong.
More importantly, if you had paid even a few seconds of attention to any of the "booster" cases that have ever been publicized, you would realize that no wealthy booster actually reaches into his own pocket to fund "winning another ring". These cases will ALWAYS involve a booster using a legal entity, such as a business or charity, to disguise the true nature of the dealings. So while these boosters LOVE to have people think that the beneficence is coming from them personally (and the first layer of analysis and discussion would certainly involve the individual booster, since a student-athlete usually has no idea whether that booster will ultimately hide that payment on the books of a legal entity), the reality is that the forensic accounting will usually find the substance of the illicit transactions buried within a legal entity. Therefore, the boosters are usually throwing around other people's money (which they may, in fact, have control over).
You are entitled to think that if the IRS (and/or state revenue departments) finally wades into this area, that nothing will happen. That's on you. You are free to underestimate this jeopardy if you so choose. But I guarantee you, the next big fight that Donald Trump faces will not involve the launch of his social media platform, but will be with the legal authorities in New York (both fed and state).
And tax prosecution usually does not end well. Or cheaply.