>Covey, 84, a Missouri native and former U.S. Marine Corps basketball player who earned a law degree from Columbia Law School in 1955, uses the words “romantic” and “beautiful” to describe the most elegant tax maneuvers.
This guy is a hacker.
What I've always wondered is why people don't load the tax code into the automatic proof systems and let it do some goal seeking. The idea of putting money into a trust and then taking it out took a while to occur to Covey. All the "useless" edge cases would be explored by a goal seeking system. There are probably a large number of these hacks out there already discovered, but taking it all the way through to a tax court decision is the real trick. I also vaguely remember a legal principle that if a transaction was entered into soley for the purpose of lowering taxes, and with no other business goal, it can be disallowed unless that was the intent of Congress.
There have been a number of conferences over the years on the general topic of AI and the law. I once read in a general book on business strategy about how a contract can be either a sale or a lease, but that it is often extremely valuable to make a sale appear to be a lease, and vice versa. Lawyers will craft twenty pages of dense legalese to hide the facts from the casual reader. Someday a sophisticated text processing system will ingest a contract and give the answer, along with the chain of inferences from the obfuscated language (to show the judge).