Backdoor Taxation of Your Tax-Free Roth? December 29, 1997March 25, 2012 Dave Allman: "I’m 46 with a $250,000 zero basis IRA and the Roth conversion numbers absolutely make sense, if I can meet the $100,000 AGI cutoff. My concern is the "tax risk" of assuming that today’s law will control in 20, 30 or 40 years. It wasn’t long ago that Social Security wasn’t taxable (okay, special case, but point is the same). Any speculation on the risk of paying taxes today only to have to (perhaps) pay them again someday?" It’s a real risk, though there will be lots of senior voters by then to keep Congress from daring to do it directly. The Roth would never be taxable per se, I suspect. But if they decided that income from your Roth IRA should be counted in determining your eligibility for Social Security or other benefits, say, or in figuring some 21st century alternative minimum tax, it would amount to much the same thing. The best you can do is make some educated guesses, comfortable in the knowledge that, by and large, whatever choice you make is secondary in importance to the fact that you’re saving in the first place. That’s the big decision, and either way you go — traditional IRA or Roth IRA — you’re making it right.