The latest is that Trump could be criminally charged for tax evasion by paying for some benefit to an employee rather than salary. The Internal Revenue Service (IRS) was looking at taxing frequent flyer bonus points as income to an employee when the company pays for the flight, but the employee uses the bonus point for themselves. They are saying Trump offered to pay school fees and that is a crime. This has always been a gray area. Banks often paid for apartments in places like Tokyo for employees to live in while there but the lease was in the company name. Often the rent for apartments was very expensive to the point transferring an employee to Tokyo would not work unless the company paid the rent. Does that become personal income?
Unlike gifts made on a personal level, gifts from an employer to an employee (outside the context of employment) are generally taxable to the recipient as supplemental wages. In other words, the gifts are subject to both income tax and employment taxes. IRS doesn’t really even have a concept of a ‘gift’ in their vocabulary. It has considered having a coffee machine at work at least de minimis. Believe it or not, there were people arguing if an employee was given coffee and a donut every day for breakfast at work, that should be taxable.
This is one huge grey area. Even doing business, if you did a contract and then bought them tickets to Disneyland for their family, now you are violating the Foreign Corrupt Services Act, for which the SEC will put you in prison under the theory it is a bribe. Essentially, where a person could buy a friend dinner, an employer cannot buy an employee dinner for that is a taxable benefit. This is the problem with income taxes. Those in power see if you find a dime in the parking lot, legally you owe them 5 cents.
I am sure that the NY prosecutors could walk into any of the Wall Street banks and criminally charge everyone under these sorts of theories. But then again, they are not running for president.
