There is a flat out rule against it at U.S. brokerages because its seen as a bucket shop tactic to encourage it in order to double the spread take. I seem to recall so potential issues with big prop shops having left hand not knowing what the right had was doing issues and inadvertently triggering this by opposite positions taken by different segments of the operation (or course it would seem good business practice to net this internally anyway). The folks who do allow it probably aren't super concerned about AML rules, but I agree, if you did manage to make it happen in a real brokerage they would probably take a dim view. Although you can't really launder money that way unless you have an advisor account with multiple customers and the advisor allocates trades at the end of the day or you have separate entity accounts that are doing pre-arranged trades between one another on high bid/ask spread products.The AML people at the firm or clearinghouse will "very likely" take a hard look at this. It comes off looking as classic AML or a tax game. It may not be either, but the AML folks are gonna go nuts - especially if it shows as two clearing numbers. As Robert pointed out if they are 1256 you'll have to mark at yearend.
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