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With no offense meant to your unparalleled ingenuity, do you really think you could come up with a sure-fire double your money scheme that someone else hasn't already thought of, thus rendering it, as Mr. Market will do, ineffective?

he's not really talking about doubling his money --he's talking about 'avoiding' some taxes.

• convert $X from t-IRA to Roth(1)
• convert $X from t-IRA to Roth(2)

as it sits, there's income tax on 2X

• in the two Roths, bet opposite directions (eg, buy calls in one, sell calls in the other; buy stock in one, sell short in the other; bet on Philly in one and Dallas in the other)

• one bet wins ,the other loses. so Roth(1) ,say, has $2X, Roth(2) has $2

•recharacterize loser's (Roth(2)) $2 back to t-IRA

••Op's theory is that he now has $2X in Roth(1), but only owes taxes on
$X ..loses the transaction costs, but gains the tax on $X

.... i had a similar idea several years ago ,moving money from IRA to taxable ..can't recall why i decided it was dumb and Dumb <g>
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