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Hoots : Should I sell and rebuy stocks before the end of the year to trigger a gain and offset capital losses? This year the market has been volatile and my portfolio has hardly gained. I was forced to sell some stock earlier to - freshhoot.com

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Should I sell and rebuy stocks before the end of the year to trigger a gain and offset capital losses?
This year the market has been volatile and my portfolio has hardly gained. I was forced to sell some stock earlier to buy into another investment opportunity and chose to sell two stocks that had substantial losses. Right now my capital losses are in the ,000 - ,000 range (I haven't figured it out exactly yet).

I've never had net capital losses in a year before. How do I best apply them to my taxes for 2016? Does it make sense to sell stocks that are currently positive and repurchase them immediately, so that the cost basis is brought up to current value and any taxes on that gain are offset from my losses?

Assume that these stocks have all been held more than one year. Also assume that I have no income and thus no personal income tax to offset with these losses. I also have no depreciation of property.


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You have multiple issues buried within this question. First, we don't know your tax bracket. For my answer, I'll assume 25%. This simply means that in 2016, you'll have a taxable ,650 or higher.

The interesting thing is that losses and gains are treated differently. A 25%er's long term gain is taxed at 15%, yet losses, up to 00, can offset ordinary income. This sets the stage for strategic tax loss harvesting. In the linked article, I offered a look at how the strategy would have resulted in the awful 2000-2009 decade producing a slight gain (1%, not great, of course) vs the near 10% loss the S&P suffered over that time. This was by taking losses in down years, and capturing long term gains when positive (and not using a carried loss).

Back to you - a 15%er's long term gain tax is zero. So using a gain to offset a loss makes little sense. Just as creating a loss to offset the gain. The bottom line? Enjoy the loss, up to 00 against your income, and only take gains when there's no loss. This advice is all superseded by my rule "Don't let the tax tail wag the investing dog." For individual stocks, I would never suggest a transaction for tax purposes. You keep good stocks, you sell bad ones. Sell a stock to take a short term loss only to have it recover in the 30 day waiting period just once, and you'll learn that lesson. Learn it here for free, don't make that mistake at your own expense.


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