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"What about the 'chutzpah' trust ---- where the donor reserves the right to borrow from the trust?"-

In a Charitable Remainder Trust, there are rules against "self-dealing." I think this would keep you from being able to borrow from the trust.

Many reputable, well-established charities have "Planned Giving Officers" in their Development Offices. Most of these are able to give you good, reliable information about CRT's - and other "Retained Interest" gifts.

Through these, you can convert a highly appreciated asset into an income stream while avoiding CG taxes and receiving a (partial) charitable deduction for the gift. Remember, though, that it is a gift. The "Remainder" of the trust after its term (life, fixed term up to 20 years, or life + fixed term) must go to a qualified 501(c) charitable organization. Taxes are due, of course, on income received from the trust.

This is also an irrevocable trust. You can't give it and decide you want to take it back! One form of the CRT allows you to profit from growth in the trust since the payment is a fixed % of the value of the trust. Another form is a fixed payment (a % of the initial value of the trust).

There are also probability tests that insure the charity will actually receive a benefit (or that the probability is there) of at least 10% of the initial value.

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