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- you use the auction house hack to inflate the value of the painting from $1_000_000 USD to $20_000_000 USD buy buying it from yourself

Isn't that a realization event right there?

Obviously, the described scheme could still work if you sold one painting to yourself, and then donated N paintings based on that valuation.

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"The federal tax code allows you to contribute long-term appreciated securities—such as stocks, bonds, and mutual fund shares—directly to a charity without paying capital gains tax on the appreciated value, as you would if you sold it first and then contributed cash to the charity." [1]

[1] https://www.fidelity.com/viewpoints/personal-finance/tax-bre...

Sure the donation isn't taxed, but why wouldn't the original (fraudulent) sale be taxed?

Selling an item at auction and buying it yourself isn't exactly a charitable contribution.

You don't pay (an income or capital gains) tax when you buy something. Only when you sell it. Maybe there's some other tax, like VAT or luxury or sales that are all based on the purchase price.

You can of course donate $20 mil to a charity that you can influence (a foundation of a relative or a friend’s family, say) and get that charity to buy the first painting at auction.

This way you pay cap gains on 19 million but can offset 20 million of charity donations against the gain.

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