Let's say you have an investment account with millions of dollars in it. Let's say for the purpose of the example you are earning 30% a year[0]. You're accust

Let's say you have an investment account with millions of dollars in it. Let's say for the purpose of the example you are earning 30% a year[0]. You're accustomed to use that account to fund your travel. You convert some securities to cash to buy plane tickets to travel all over the world. You're going to pay capital gains taxes, or just income taxes, on those conversions to liquid capital. If instead you donate those securities to a "Charity", then the earned interest is not taxed, and you receive a tax benefit for moving the property to the charity entity. If the charity is happy for you to travel all over the world, then you're done. Same benefit accrues, tax burden becomes negligible. What's left to determine (from our electronic armchairs) is: Does the charity do good for the nation, for the world, to an extent that it's worth forgoing the tax income? I expect that the answer is "Yes" for several of the charities we consider household names. I expect that the answer is "No" for the overwhelming majority of charities, by count or by endowment. We could start by taxing Harvard. :) [0] Not that anything is dependable year on year, but that's the rate that university endowments made in 2021.