Taxes when you have minimal records.

[MicroBob]

I really don't know what the best way to do it would be.


Claiming excessive losses can likely set off red-flags I would think even if they're legit.
In other words: I think that claiming $1,000 in wins and that's it would likely just slide on by.
If you claim $12,000 in wins and deduct $11,000 in losses then the IRS might be more likely to ask "what the hell is going on here?" even though you are just playing by THEIR rules.


to the other poster...regarding reporting one's winnings from previous years. Not sure how much we're talking about here.
If it's minimal stuff then I would be less inclined to worry about it.
If it's pretty significant then I really don't know.
You could just lump it all in for this year...and if they ask what happened you can explain that you are now learning that you needed to report your winnings from previous years so you are just doing that.
They might not like that very much...or they might think you are a wonderful guy for trying to do the right thing.
Don't know.
I might consider asking a tax-professional about this.
Just tell him that you won X-amount in previous years and never reported any of it and that NOW you are starting to get worried that perhaps it will come back to haunt you.
Do you have anything to worry about?
Are they really going to check your PREVIOUS year's records?
Who knows.
Anything's possible.
A tax professional may be worth your time on this one....I suspect it's not uncommon to decide "hey...I owe taxes from such-and-such from 3 years ago that I forgot to report....and I'm a little panicky that the IRS will think I'm up to something devious." but I just don't know what the best course of action for such a situation is.

[Jeffage]

If the amount you didn't claim last year is significant, you can file an amended return. You'll need an accountant to help with this.

Disclaimer: I'm not an accountant.

Jeff