Tax Question

[Port Conway Lane]

I won $5,000 in a free online contest. Can I write off $1,800 in gambling losses against that? Because the contest was free I thought I couldn't but called h&r block and the guy said I could but it wouldn't be worth it unless I had enough itemized deductions on schedule A blah blah blah. I have nothing to itemize and didn't quite understand what he was trying to tell me. Any tax experts out there ? Thanks