I'm a CPA - had one of those clients that was both stupid and arrogant - but they were rich.
They would go to Vegas a few times a year and gambled enough that the trips were comped. They bragged that they ALWAYS made money on their trips. At the end of the year they would dutifully provide me their 1099's for their winnings, which were substantial.
But, once she gave me the report from the casino that showed they actually put more money in than they won. I told her we could deduct those losses to the extent of the winnings.
She insisted that report was way off and that they would certainly go to jail if they claimed those losses.
So, they needlessly paid tax on 6 figures of winnings just so they could brag about how much money they made in Vegas.