Originally Posted by jdog View Post
Technically in this case Aunt Louise could report a $600 gambling loss if she was able to benefit from itemizing all her deductions. However most people do not, so in this case it would be entirely legal for her to not report anything when using the standard deduction.
I could be misinformed, but afaik, it's required to report the total of winning sessions as income. In Aunt Lou's case, that's $300.

Then the itemized loss would be limited to $300.