http://sivers.org/book/SmartestInvestmentBook
EDIT: Just read the wikipedia article he links to, and as the value of the trust is recalculated each year, and his annuity is based on the recalculated value (as opposed to the original value) it's effectively impossible to deplete the value.
Also, you can setup a net-income CRUT that pays out the lesser of the annuity income percentage, or the trust's net income for the year, thus ensuring that your annuity doesn't reduce the value of the trust from year to year.
Bashing numbers helps me visualize this...
Looking at (nearly) the worst case, if the trust earns zero interest, he will be draining it by 5% per year, so the principle will be
0.95^y * 22e6
where y is the number of years. If he lives for 40 more years... 0.95^40 * 22e6 = 2.8e6
(13% of the original sum is left).A less drastic case would be earning 4% but paying out 5%, i.e. losing 1% per year.
0.99^40 * 22e6 = 15e6
(67% of the original sum is left).OK, the absolute worst case is he invests the whole amount in subprime mortgages and loses it all. We won't bash those numbers, obviously he is a lot smarter than that.