This is a bit of a vague question and hence a longshot as far as gaining an understanding...
Has anyone come across tax planning arrangements whereby a company and the shareholder/director enter into cross bets with each other, the individual will win the bet and hence the company pays out to that individual tax free?
Sorry but I have no other details.
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No
You may be thinking of a contract for difference, but that's not the same thing. And what happens if the company wins the bet more often than the individual?
This scheme has been around a few years
And is quite well known. I even saw it advertised on the internet the other day. You have not quite described it properly though.
Casino - bank?
You mean the casino bank scheme?
http://www.taxresearch.org.uk/Blog/2012/07/13/how-to-cheat-at-tax-one-en...