Skip to main content
Message Font: Serif | Sans-Serif
No. of Recommendations: 1
It is obvious that I do not understand the "wash-sale" and "replacement shares" of trades which, in the past, I did frequently building up a considerable long term loss and deferred loss.

Also, due to reverse splits interesting things happened involving options with this stock which recently expired.

Specifically: I now have 10 shares of a stock (DUST) which my broker is carrying at:
Purchased: 6/4/2019 Price paid=421.51 Long
How can I sell this stock to generate a long term loss without triggering more "wash sales and or replacement shares"?

I am 81 years old and am now ready to throw in the towel as it seems no matter what I do, I always have lots of short term gains (to pay taxes on), and all my long term losses become "deferred"; losses which I can only take at the rate of $1500 per year. If I throw in the towel and live to 250, I might be able to use them all up.

I have also considered selling covered calls on stocks more than a year out. If they are called out at expiration, any gain would be long term since they had been held more than a year. Is that correct? If they are NOT called out, I could either sell the same covered call again, or sell the shares at whatever they were priced at expiration and generate either a long term gain or loss. Is that correct?

I am having memory problems and the rules are so confusing I cannot get a grasp on them.

I enjoy this board very much as well as a few others and wish you all well.

I thank you for any advice or help you can give an "old guy" that is starting to lose it all. The entire port is only 200-250K but retirement income, housing, and health care are not a problem for me.

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.