If he's engaged in debt parking on this, you'd call that "legitimate?"
You can't do that legitimately in the US. But let's assume, for argument's sake, that he did exploit a real legitimate loophole, a mistake in the tax code, some provision that was never intended to allow someone to escape some tax liability. Yes that's legitimate.
I know that sounds crazy, but how can you tell the difference, really, between a mistake in the tax code and a provision in the tax code? Like, for example, taking a mortgage deduction on a yacht... that's clearly an abuse right? Except congress specifically made it ok to take a mortgage deduction on a boat if it had sleeping quarters, etc. So it's a provision. Is setting up your company headquarters in Deleware to avoid state income tax a loophole or a provision? It's allowed under Deleware law.
There's an example where someone who raised sod for sale was able to be considered a miner of an exhaustible natural resource and was able to take a deduction on the sod as a "natural deposit". That's clearly not what was intended by "natural deposit" or "exhaustible resource" right? Well, if the law allows you to declare your sod an exhaustible resource, that's what it is. We're not talking about getting away with something that violates the letter of the law, we're talking about trying to ascertain the "spirit" of the law, and that's often a very difficult thing to do with the tax code. Because the "spirit" of the tax code is friggin bizarre. In some cases, the "spirit" of the law is that some congressman wanted a provision (maybe including "sod" as a natural resource) to please a voting bloc, or influential group, or contributor. And in the "spirit" of compromise to get the bill signed, it was added as a nonsense provision that everyone knew was a joke, but was fully intentionally added into law. So when a sod farmer who had nothing to do with that comes along and realizes that they have an opportunity to take a natural deposit deduction, what are they to do? Assume that it's a mistake? It may not be.
Tax law is so convoluted that I think the only thing that makes any sense is to determine whether what the person did was legal. There is no "right" when it comes to the US tax code, it's all wrong. All of it violates equal protection, every bit of it should be tossed on its ear.
I think in this case, perhaps it's a bit of a catch 22. Especially if there is something shady to be found. General ignorance of tax codes will only hurt so much. In fact, it could be used to his advantage in a debate if Hillary did try to use it against him. If everything is on the up and up, then simply return citing the codes he followed, the reason things are the way they are and tell her to have her people fact check it. It won't sway people that are already firmly entrenched on one side or the other, and the people who haven't decided should be able to use Google.
But if he doesn't, it definitely looks suspicious. It doesn't matter if he is or isnt following regs since there is no proof other than his word. We all know how he feels about libel, but I'm certainly not of a mind to trust him.
Every one of my buddies in California is a tax fraud, and probably everyone I know in Texas. I posted on this site recently that Texas has a provision where if you buy something online and don't pay sales tax on it you're supposed to get a sales tax form from the county and mail your sales tax to the state. I'd be surprised if anyone in the history of the state has done that. They all just buy their tires off of tirerack.com, grin about not paying sales tax, and move on - tax frauds. In California you're supposed to disclose internet purchases on your income tax form if you don't pay sales tax. Nobody I knew there did that (except myself).
I'd imagine that I could make a tax fraud/criminal out of almost everyone if I took their tax returns and gave them to an angry 50% of the US populace to find flaw with. The only people that might get away from that are people who are career politicians and knew that they'd have to release their tax forms to the public, and so would comply with every last word.
