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How is this legal? Let's assume he lost the money, how would this show up in the companies books?

Let's assume he lost the money, how would this show up in the companies books?

I'd be more curious how the winnings were reported on the books. That's a lot of back tax penalties.

The company books would probably just show a loan. Then he could loan/repay the company with his winnings.

You usually can't issue a loan to an executive without some sort of director oversight. See Tyco.