You live in the U.S.?
You might want to check this forum:
https://forumserver.twoplustwo.com/5...ted-rich-muny/
And this thread:
https://forumserver.twoplustwo.com/5...-poker-740589/
But I would report it as a $16,000 win and no deduction. And I'd include an attachment with my tax return explaining what happened.
*DISCLAIMER: THE ABOVE IS NEITHER LEGAL NOR ACCOUNTING ADVICE AND IS NOT TO BE CONSTRUED AS SUCH. YOU COULD CONSULT AN ATTORNEY OR ACCOUNTANT IN YOUR JURISDICTION*