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One rule of thumb in investing says that you should pay no tax before it is due. But because of the current transfer tax landscape, prepaying taxes—by making taxable gifts in 2010—is a strategy families of means should at least consider. The risks involved in prepaying taxes are well-known: Doing so can reduce precious liquidity, and in the worst-case scenario investors could end up paying a large tax bill they might have been able to avoid down the road. So it’s critical to first gauge the potential benefit. In the following pages, we have used Bernstein’s Wealth Forecasting System to examine the merit of making taxable gifts in 2010.

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