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Actually, I can't figure out how to do this with options.

Conceptually, what I really want is "ILikeBeer Inc's Coin Toss investment". Imagine that ILikeBeer Inc. has 2 classes of shares, "Heads" and "Tails", par value $1 each.

I convert $10,000 from my traditional IRA into my Roth "Heads" account and buy 10,000 shares in "Heads"
I convert $10,000 from my traditional IRA into my Roth "Tails" account and buy 10,000 shares in "Tails".

Then the next day ILikeBeer Inc. flips a coin and
- if it's heads, ILikeBeer Inc. declares a $2 dividend to the Heads shares
- if it's tails, ILikeBeer Inc. declares a $2 dividend to the Tails shares
... and then ILikeBeer, Inc. files for bankruptcy, penniless.

Coming back to my Roth IRAs...
- if the result of the coin toss was heads, then my Heads account now has $20,000 cash in it, and my Tails account is worthless. I recharacterize the Tails account back to a traditional IRA so that I don't pay tax on the conversion.
- if the result of the coin toss was tails, then my Tails account now has $20,000 cash in it, and my Heads account is worthless. I recharacterize the Heads account back to a traditional IRA so that I don't pay tax on the conversion.

Either way I have successfully moved $20,000 from the traditional IRA to the Roth, I now have one Roth IRA account with $20,000 in it but I think I only have to pay tax on the $10,000 what was in the successful acocunt when I converted it. That's the goal of this strategy.

Unfortunately ILikeBeer Inc, doesn't exist. I was thinking I could do this somehow with options but I'm pretty sure my broker won't allow me to write calls unless they're covered, and I think covered calls won't work here.

Any ideas???

Thanks in Advance!
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