Offer your thoughts or opinion on the input financial query or topic using your financial background.

Strategy to minimize taxes due to unpaid wages?
Can I write off the $56,000 based on demand letters? Or do I need to   finish suing him to write-off the loss? No and no. You didn't pay taxes on the money (since you didn't file tax returns...), so what are you writing off? If you didn't get the income - you didn't get the income. Nothing to write off. Individuals in the US are usually cash-based, so you don't write off income "accrued but never received" since you don't pay taxes on accrued income, only income you've actually received. Should I file the 2012 taxes now? Or wait until the lawsuit finishes? You should have filed by April 2013, more than a year ago. You might have asked for an extension till October 2013, more than half a year ago. Now - you're very very late, and should file your tax return ASAP. If you have some tax due - you're going to get hit with high penalties for underpaying and late filing. If the lawsuit finishes in 2014, does it apply to the 2012 taxes? Probably not, but talk to your lawyer. In any case - it is irrelevant to the question whether to file the tax return or not. If because of the lawsuit results something changes - you file an amended return.