: How did historical high tax rates work in practice? For at least half of the 20th century, the upper tax bracket rates were very high, over 80% in most cases: How did this work in practice? I contend that the US has always

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I remember in the 19th and early 20th century was the problem of Trusts set up by the wealthy to avoid taxes (hence the term "Anti-Trust")

That's not what antitrust means. The trusts in that case were monopolies that used their outsized influence to dominate customers and suppliers. They weren't for tax evasion purposes. Trusts were actually older than a permanent income tax. Antitrust law was passed around the same time as a permanent income tax becoming legal. Prior to that income taxes were temporary taxes imposed to pay for wars.

The primary ways to evade taxes was to move expenses out of the personal and into businesses or charities. The business could pay for travel, hotels, meals, and expenses. Or a charity could pay for a trip as a promotion activity (the infamous safari to Africa scheme). Charities can pay salaries to employees, so someone could fund a charity (tax deductible) and then use that money to pay people rather than giving gifts. If you declare your house as a historical landmark, a charity could maintain it.

Subscribe to magazines at the office and set them in the waiting room after you read them. Use loyalty program rewards from business expenses for personal things. Sign up for a benefit for all employees at a steep discount and pay everyone a little less as a result. Barter. You do something for someone else (e.g. give them a free car), and they return the favor. Call it marketing or promotion ("Trump is carried away from his eponymous Tower in a sparkling new Mercedes Benz limousine.").

Another option is to move income and expenses to another tax jurisdiction that has even fewer laws about it. Where the United States increasingly cracked down on personal expenses masquerading as business expenses, many jurisdictions would be happy just to see the money flow through and sit in their banks briefly.

Tax policy is different now than it was then. Many things that would have worked then wouldn't work now. The IRS is more aggressive about insisting that some payments be considered income even if the organization writes the check directly to someone else. It's unclear what would happen if United States tax rates went back to the level they had in the fifties or even the seventies. Would tax evasion become omnipresent again? Or would it stay closer to current levels.

The rich actually pay a higher percentage of the overall income taxes now than they did in the forties and fifties. And the rich in the United States pay a higher percentage of the taxes paid than the rich in other countries with higher marginal rates. Some of this may be more rich people in the US than other countries, but tax policy is part of that too. High income taxes make it hard to become rich.