I'm surprised the article didn't mention CRUTs (Charitable Remainder UniTrusts). The idea here is that you "donate" an asset that has immense unrealized capital

I'm surprised the article didn't mention CRUTs (Charitable Remainder UniTrusts). The idea here is that you "donate" an asset that has immense unrealized capital gains taxes attached to it. The donation sits in a trust, that pays you back a certain percentage every year until you die. Once that happens the remainder goes to a charity of your choosing. The benefit of it is the following: 1. You aren't taxed on any of the unrealized gains the asset had when you donated it. 2. The trust receives tax free growth. 3. You are taxed on the percentage you get back using something called the four tier rules of CRUT taxation (explained further here: http://floridadomicilehandbook.com/2009/12/11/the-four-tier-rules-of-crut-taxation/ http://floridadomicilehandbook.com/2009/12/11/the-four-tier-...). Basically, any money you take from the interest is taxable, but the principle is not. 4. You get a tax deduction for the full amount (which can be spread over 5 years. For each year, up to 30% or 50% of your AGI can be deducted, depending on whether the original investment was long term or not) It sounds fair, but in reality it's easily gamed. You just take out the highest percentage you are allowed each year, and invest in the safest low-earning investments possible. In this way, most of what you pull out is principle, which isn't taxed at all. Given that and the fact that you can deduct the donation from your other income, you can, in effect, pay negative taxes on it. More info can be found here: https://en.wikipedia.org/wiki/Charitable_trust#United_States https://en.wikipedia.org/wiki/Charitable_trust#United_States It's a lot better than it used to be. In 1997, congress cracked down on it, (http://www.mclaughlinstern.com/docs/publications/pub_kosakow_16_new_proposed_regulations_challenge_accerlerated_charitable_remainder_trusts.pdf http://www.mclaughlinstern.com/docs/publications/pub_kosakow...) but it's still a mighty windfall if you're looking to store some of your wealth in safe investments.