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Selling a Stock to Reduce Your Income Tax - By John R. Bullis

Updated: Mar 30, 2023

No one I know makes 100 decisions and finds all 100 were right or good decisions. We all make mistakes. If you purchased a stock say for $10,000 and the value has gone down to $6,000, maybe you should consider selling it to recognize a capital loss. Capital losses are deductible first against any capital gains (both short term and long term). Sometimes there are some capital gains that are part of the dividend distributions. And, you can deduct $3,000 of the rest of the capital losses on page one of your income tax return. The unused capital loss carries over to the next year. By having enough capital losses to offset your capital gains and get a $3,000 deduction, you will reduce the income tax. If you still believe in the stock, you can sell it to recognize the loss and after 31 days, buy it back. The “wash sale” rule prevents the loss from being deductible unless you wait that long before buying it back. I hope all of your stock investments have gone up, but it is not unusual if you buy individual stocks to have one or more that have gone down in value. If you were thinking of making a gift, ie to a relative, it is best to sell the stock that has gone down to less than your purchase price. Then you recognize some tax savings from the capital loss and can give the cash to your child or other relative. Sometimes folks will buy a stock directly from the domestic (US) company. If the company is a “small” business-has less than $1,000,000 in capital, then it may qualify as section 1244 stock. Any loss on sale of section 1244 stock has a special rule that allows a full ordinary loss deduction of up to $50,000 for single taxpayers and $100,000 deduction for married individuals filing a joint return. We’ve seen a few examples of where the stock qualified as section 1244 stock. The loss on sale of that stock gives more deductions and saves a lot more tax than capital losses do. Did you hear “Sometimes the best things are right in front of you; it just takes some time to see them.” Gladys Knight, a singer.

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