Trump absolutely 100% broke the self dealing rules for his foundation
Trump is no tax genius, because he broke the rules regarding direct self dealing. It's right in Fahrenthold's article. So bear with me and let's just think about this...
Self Dealing Defined:
IRC 4941(d) provides that the following transactions are generally considered acts of self-dealing between a private foundation and a disqualified person: E: Transferring foundation income or assets to, or for the use by or
benefit of, a disqualified person
So in English a charitable foundation can't buy you stuff if you are a substantial contributor. Which Trump is.
A disqualified person is: A substantial contributor to the foundation (as defined in IRC 507(d)(2));
https://www.irs.gov/pub/irs-tege/eotopicq85.pdf
So we can agree there's no question that Trump is a disqualified person and cannot receive any personal benefit from the Foundation. In the WaPo story there are numerous examples of how Trump benefitted, but many of those benefits are "indirect." Some of these indirect benefits, like fixing the fountain in a public space that indirectly help his property values are tolerated by the IRS. They're super skeezy and the kind of thing done by irredeemable people, but allowed. However, there are smaller transactions listed and as with everything in the law, the devil is in the small details.
Then he used $100 of the foundation’s money to buy a two-person membership to the Metropolitan Museum of Art.
https://www.washingtonpost.com/politics/trump-boasts-of-his-philanthropy-but-his-giving-falls-short-of-his-words/2016/10/29/b3c03106-9ac7-11e6-a0ed-ab0774c1eaa5_story.html?utm_campaign=pubexchange&utm_medium=referral&utm_source=huffingtonpost.com
Whoops. That ain't legal Mr. Trump. Here's what the IRS has to say about that.
Membership dues and fees, by their very nature, are usually paid by individuals on a continuing basis. When dues are paid by a private foundation on behalf of a disqualified person, it may be presumed that the disqualified person is being relieved of the obligation, whether or not legally enforceable, to make such payment. The benefit conferred on the individual is not incidental or tenuous, but is direct and economic in nature. Accordingly, Rev. Rul. 77-160, 1977-1 C.B. 351, holds that the payment of membership dues by a private foundation on behalf of a disqualified person is an act of self-dealing under IRC 4941(d)(1)(E).
And here's the point. Agents at the IRS and courts have burned a lot of calories on these rules. You can't just say, "Pssssssh, it's just $100. What's the big deal." Well, the big deal is IRC 4941(d)(1)(E). IT'S IN VIOLATION OF THE IRS CODE. There doesn't seem to be a "nominal direct dealing exception." Meaning that if the foundation gives a disqualified person $100 thats not legal.
This is akin to the bank teller who was caught taking $20 out of the drawer. The bank isn't going to die with that loss. But can the teller say, "It's only $20?" Hell no. The bank would analyze every one of the teller's transactions and you can believe that there would be legal consequence.
At some point, willful direct self dealing becomes criminal if it is implemented as a fraudulent tax avoidance scheme. How can we be so sure Trump's tax returns are clean? Gotta see the returns.
He might brag about how much of a tax genius he is, but the limited information available to us shows he ain't.
= new reply since forum marked as read
Fahrenthold deserves a finder's fee, okay the Washington Post. I've love to see Trump have to cut a check to the WaPo directly 
