Itemized deductions (gambling losses)

[havenotfiled]

What is the name of your state (only U.S. law)? FL

I have to either get a OIC or file for Chapter 7 would it be a better idea not to itemize? Itemizing over 200k in gambling losses with no way to prove the losses (no journal) sounds like the IRS would disallow them anyhow if ever audited.

 

[OHRoadwarrior]

Losses deducted cannot exceed winnings claimed. Sorry.

 

[havenotfiled]

Losses deducted cannot exceed winnings claimed. Sorry.

I may not have been clear. Example below

2009 - 50k won that I am itemizing as 50k loss
2010 - 50k won that I am itemizing as 50k loss
etc

What I am asking is should I even bother itemizing seeing how I can not prove the losses (no journal) and I plan on trying to get a OIC or filing Chapter 7. The IRS will probably not allow the write offs anyhow without a journal.

 

[LdiJ]

I may not have been clear. Example below

2009 - 50k won that I am itemizing as 50k loss
2010 - 50k won that I am itemizing as 50k loss
etc

What I am asking is should I even bother itemizing seeing how I can not prove the losses (no journal) and I plan on trying to get a OIC or filing Chapter 7. The IRS will probably not allow the write offs anyhow without a journal.

The IRS is not necessarily going to disallow the losses just because you have no journal. If the losses are real, you should claim them. If you still have access to bank and/or credit card statements that might demonstrate where your money went during the tax years in question that might also be helpful.

One significant problem (other than the obvious) of waiting so late to resolve tax issues is that access to records becomes infinitely more difficult after a few years.

 

[tranquility]

What is the name of your state (only U.S. law)? FL

I have to either get a OIC or file for Chapter 7 would it be a better idea not to itemize? Itemizing over 200k in gambling losses with no way to prove the losses (no journal) sounds like the IRS would disallow them anyhow if ever audited.

There is a 100% chance you don't get them if you fail to claim them.

Talk to the people you gambled with. They often have records of people who lose so much. It's good business to know who is paying to keep the lights on. Start trying to document it in every way possible. See a tax professional with what you come up with to see if you can get plan together on how to file.