Right, I didn't think what he was describing was all that risque. What I'm trying to figure out is if there is a way to sell a cash-secured put on a way OTM option from the IRA then buy that put in the taxable account. Then let it expire worthless. Could that transfer money into the IRA and nab a tax loss deduction in the taxable account?
The problem is that you get into wash sale rules [0]. Most people are not aware of this, but wash sales can be impacted by securities owned in retirement accounts [1].
Worse, the aspect of options and "substantially similar" securities starts to get arcane fast. Meaning, you really want a tax lawyer involved on a complex transaction like that. Otherwise, you may find that you've apparently made a ton of money, and then a few years later the IRS knocks on your door and asks for all your profits in a nice check paid to US Treasury.
(I'm not saying you can or cannot do this, only that the tax law gets complicated fast.)
EDIT - meant to add that "sale or other disposition" includes the expiration of an option. So you don't actually have to sell to incur the wash sale situation.
perhaps it's possible through enough layers of indirection to create plausible deniability... but generally this type of transaction would be considered self-dealing, which is illegal.
How would you even do it, as a nobody with no connections? You have two accounts and your broker isn't linking them up for you.
Making a sham trade at an arbitrary price with yourself is not what I was describing. My idea was the calls and the puts are as close to at the money as possible, and the counterparties are just random people with no pre-arrangement.
If you're going to simply do fraud, then the constraints don't seem interesting to me.
Not directly related but if you create synthetic positions, say you use derivatives to exit a position while still holding the asset you’re supposed to report it as a sale for tax purposes. Complex positions often are not perfectly hedged sometimes to prevent this as the tax benefit exceeds the risk.
