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Hi Malatu!

First of all, the Tax Strategies board is commonly used for this type of question and there are professionals that frequently respond to them: http://boards.fool.com/tax-strategies-100155.aspx?mid=308697...

As for your question, in general it is not advantageous to do as you propose. Stock losses can be used to offset taxable income. Up to $3,000 year can be written off on line 13 of Form 1040 that would reduce your adjusted gross income and, consequently, your tax. Amounts over $3,000 are carried forward and used up on subsequent years. Now, if you sell stock at a profit, the losses offset those capital gains first. Usually capital gains are taxed at a lower rate than ordinary income. So, by selling you may end up paying higher taxes, resetting the clock on the holding period of your (winning) stocks and paying commissions.

Hope that helps,

- zol
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