It's not that these things cannot be run - they can - but there is a set of regulations in this country that govern them as to how, as well as responsibilities of both the sponsor as well as the winner that neither are likely to be aware of in this case. Not trying to rain on the fun, but rather to inform people so they are aware of the implications they open themselves up to if they participate. It may be surprising, but you cannot just outright give your own money away to people in this manner legally without certain requirements.
If it isn't a declared value item (e.g. "This is $900 worth of art you are winning!") it's a lot easier to feign ignorance in the receipt of such things because the actual value of the transaction is nebulous. In the US you are technically required to file taxes (via Form 1099) on ANY prize value amount you receive (in the form of cash or otherwise.) This is especially true for anything over the magic amount of $600 USD. Is the IRS likely going to ever find out if you take the cash and don't file it and feign ignorance? Probably not, but the exchange and paper-trail opens you up to the risk of tax evasion if either party involved is ever randomly audited. It sucks, but it's unfortunately the law. :(
It's not that these things cannot be run - they can - but there is a set of regulations in this country that govern them as to how, as well as responsibilities of both the sponsor as well as the winner that neither are likely to be aware of in this case. Not trying to rain on the fun, but rather to inform people so they are aware of the implications they open themselves up to if they participate. It may be surprising, but you cannot just outright give your own money away to people in this manner legally without certain requirements.