Skip to main content
Message Font: Serif | Sans-Serif
No. of Recommendations: 26
I'm in the process of readjusting my taxable portfolio. It is about 51 percent equities, and I'd like to bring that down to about 40%.

The problem is that all of the positions show big gains. OK...they are long-term, but I'm afraid that sales will leave me with a big income tax bill next year.

In the past, I've offset gains with losses. What other strategies could I use?

Get some information about an overpriced stock in a company that's about to file bankrupcy, buy a lot of it, lose your investment, et voila! No cap gain to worry about when everything nets on your Schedule D.

Or you could count your blessings that you've nothing but winners and pay your maximum 15% tax on long-term cap gains. You can, of course, just leave things alone and not rebalance, but I assume that there's a reason you want to reduce your equity exposure. Don't let the tax tail wag the investment dog.

Rule Your Retirement Home Fool
Print the post  


In accordance with IRS Circular 230, you cannot use the contents of any post on The Motley Fool's message boards to avoid tax-related penalties under the Internal Revenue Code or applicable state or local tax law provisions.
What was Your Dumbest Investment?
Share it with us -- and learn from others' stories of flubs.
When Life Gives You Lemons
We all have had hardships and made poor decisions. The important thing is how we respond and grow. Read the story of a Fool who started from nothing, and looks to gain everything.
Contact Us
Contact Customer Service and other Fool departments here.
Work for Fools?
Winner of the Washingtonian great places to work, and Glassdoor #1 Company to Work For 2015! Have access to all of TMF's online and email products for FREE, and be paid for your contributions to TMF! Click the link and start your Fool career.