Also the complexity isn't all tax breaks and loopholes. Much of it comes from the need to precisely specify things. I remember several times when in my tax cla

Also the complexity isn't all tax breaks and loopholes. Much of it comes from the need to precisely specify things. I remember several times when in my tax classes in law school looking at the history of complicated provisions and finding they started out as short and simple provisions whose meaning was obvious to anyone with common sense. But then people would find ambiguities that could give them a favorable tax result. There would be a court fight over it, and eventually the provision would be change to be more precise. And so what had been short and simple because longer and more complicated. I don't remember all the details (law school was 30+ years ago and afterwards I decided I'd rather go back to programming than become a lawyer), but I remember the overall gist of one example. Some big company around the 1930s or so came up with a clever idea. Next time they were going to pay a dividend instead they did a fractional stock split, such as 1.01 to 1, immediately followed by a mandatory fraction buyback which resulted in each shareholder getting the amount of money they would have gotten if a dividend had been declared, and with no change in each shareholder's percentage ownership of the company unchanged. The company suggested that shareholders report that money as capital gains. The IRS said it was really a dividend, and the IRS won that dispute. The tax code and/or regulations were updated to reflect that. But there are legitimate buybacks that really should get capital gains treatment, and so those updated rules had a bunch of clauses and steps to go through to apply them to any specific case.