The first thing that you need to do is to actually run the numbers to see what the capital gains tax rate will be. I suspect that you are misunderstanding how the tax rates work.As long as you qualify for long term gains, they max out at 15%.http://en.wikipedia.org/wiki/Capital_gains_tax_in_the_United...Gifting the stock to a charity or someone else may save on taxes.If you need to spread the gains out over a few years without risking losing a lot, or to qualify for the long term tax rate, then you could use options to hedge yourself against price changes for long enough to get the sales spread across several different tax years.Greg
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