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I also suggest being conservative on the issue (and following the majority opinion) unless you have lots of money to burn on lawyers and are interested in your 15 minutes of fame coming from a test case in tax law.

If the IRS decided he committed a no-no 2 years later, what's the worst case scenario? Say there's a $1000 difference between the stock transactions and the IRS considers it a wash sale. What's a ballpark number for the IRS penalties and interest?

I'm thinking it would be easier to plead guilty, do the time, and move on.

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