Since it's Tax Week, I've been thinking how bothersome it is to fill out tax returns. There have also been the usual articles about how much of the income tax is paid by the top 1% of filers. I have an idea for how to save a huge amount of effort. It would have the side-effect that that same amount of tax would be paid by the top 1/2% of filers, as you'll see.
The idea is simple. People can sign up for my Double or Nothing program in December of each year. The next January 10, the Commissioner of the IRS would go on TV, standing blindfolded next to a transparent box full of red and white balls. An assistant would mix the balls and then the Commissioner would pick one. If it was red, all enrollees born Jan 1-June30 would pay no taxes, and all other enrollees would pay double the normal taxes.
This would be attractive to rich people, who could be close enough to risk-neutral and whose time is valuable enough that they'd like the 50% chance of not having to file tax returns. They'd be able and willing to dig into capital to pay their doubled tax.
It would not affect economic surplus, because the expected tax rate would be unchanged by the randomization.