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Tax Talk with George Saenz

Ask the tax adviser

A capital-gains loophole

Dear Tax Talk:
I retired early in 2000 and planned to be in the 15 percent tax bracket through 2003. I have some stock that I've been holding for more than five years, and I want to reduce my tax exposure. I should have sold some last year because my taxable income was well below the 15 percent bracket, but I didn't. The total amount of stock I should sell this year will put me into the 27.5 percent bracket, causing 20 percent capital gains on some of it. However, it looks like I may be able to take advantage of the provision that allows a "deemed sale" in 2001, though the intent may be a bit different. If I can do this, I will only pay 8 percent capital gains tax on the deemed sale in 2001.

Then, if I actually sell that same stock in 2002, I'll only pay 10 percent on the additional gain and I can sell another block and pay only 8 percent capital gains on it. That way I can sell as much stock as I should in 2002, and only pay 8-to-10 percent capital gains on all of it.

The rub is that the unplanned gain in 2001 will cause an underpayment penalty, though even with that it looks like I can save a decent chunk. This appears to be a wonderful loophole for my circumstance. Am I misinterpreting or missing something?
Bill

Dear Bill:
It's nice to get the question and answer all from one user, it cuts back on my involvement. Unfortunately, you're kind of on the hook for the underpayment penalty, and I don't see an exception there.

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Back in 1997, Congress passed a tax law that said a taxpayer can elect to treat certain capital assets sold in a deemed sale on Jan. 1, 2001. If the taxpayer makes this election with their 2001 tax return, then future gain on the assets may be taxed at a lower rate. The lower rate first applies to those elected assets sold five years after the deemed sale date, which won't be until 2006, so we don't really need to be concerned about those assets for now.

The lower rate, however, is available in 2001 for those taxpayers in the 15 percent or lower tax bracket for that tax year. The rate is reduced from 10 percent to 8 percent on those assets held more than five years for which either the gain election is made or those actually sold in 2001.

Since you didn't get around to selling your five-year assets, the election is a perfect way in hindsight to take advantage of the loophole. If you sell the elected assets within five years, you'll pay tax at the 10 percent rate on appreciation since the deemed sale date (provided you're still in the 15 percent or lower bracket). After the five years, you get the 8 percent rate on all gain if you're in the 15 percent or lower bracket, or 18 percent if you're in a higher tax bracket.

-- Posted: Jan. 30, 2002

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See Also
Stock losses could cut your tax bill
Wrong investment basis could trigger bigger tax bite
Figuring your capital gains rate
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