I read this article in the Washington Post, “This widely touted retirement move isn’t all it’s made out to be.” That’s wrong: if you save and invest well, you ALWAYS want to convert to Roth if you can stay in the 22% tax bracket. You won’t pay less than this on your topmost distributions from Traditional when you’re retired and on Social Security, and more Roth ALWAYS lowers the chance that you will pay income-related surcharges on your Medicare Part B and Part D premiums: IRMAA.
The correct, apples-to-apples conversion of Traditional to Roth is clear to me, and the article did not state this correctly. Before age 59½, pay the tax due on the conversion amount from your prior Roth contribution basis. (In “five years,” you will also be able to pay the tax from prior conversion basis. After age 59½ the steps are much simpler. I wrote about these steps before here.)
DETAILS:
== RMDs push you toward IRMAA tripwires ==
You don’t want to pay income related surcharges (IRMAA) to your Medicare Part B and Part D premiums after you are retired. The surcharges can add to $10,000s per tax payer in your retirement years. If you’ve saved and invested well, IRMAA is a real risk. About 10% of retirees pay this surcharge and the percentage is increasing.

Required Minimum Distributions (RMDs) for Traditional will push you closer and closer to the next tripwire of income that triggers a surcharge. At expected returns for stocks and bonds, in ten years your RMD will double in real spending power from the one you took in your first year (age 73 now and age 75 in 2035): your portfolio grows despite the withdrawals for RMD, and your RMD percentage increases by 50% in ten years.
== $100 in Traditional = $78 in Roth ==
You can direct $100 to Tradtional and avoid 22% tax now or you can direct $100 toward Roth, pay 22% for a net of $78 in your Roth. They’re invested the same way and increase by the same multiple over time. You have the same after-tax value for each in the future assuming you would pay 22% tax on the distribution from Traditional.
It’s the same for a conversion. You want to convert-shift $100 from Traditional and wind up with $78 in Roth. You’re shifting the same future after-tax value from one to the other. They’re similarly invested the same way and increase by the same multiple over time. You again have the same after-tax value for each in the future assuming you would pay 22% tax on the distribution from Traditional.

== Roth is always better ==
You ALWAYS win when you contribute or convert to Roth in the 22% marginal tax bracket.
1. You can’t lose with Roth because you will NEVER pay less than 22% marginal tax rate on your topmost distributions from Traditional. A relatively small amount of distributions from Traditional is truly low tax (NO TAX!) after you have started Social Security (SS) – roughly the first $15,000 distributed per taxpayer.
The effective tax rate JUMPS after this. For example, you NEVER pay 10% or 12% marginal tax on distributions from your Traditional IRA. The culprit is the math that drives the increase in the percentage of SS that’s taxed. Each $1 distributed increases $.85 of SS that’s taxed. What you may think is the 12% marginal tax bracket is an effective 22.2% tax rate: 12% times 1.85.
2. You ALWAYS win with Roth because more Roth ALWAYS lowers the risk of paying IRMAA: you have no taxable income when you sell and distribute from Roth. The amount of risk reduction for a specific contribution or coversion may be small, but your are lowering the chance of paying IRMAA.
== Correct way to pay taxes ==
You want to move $100 of Traditional to Roth in the 22% tax rate. You owe $22 tax. You want to wind up with $78 in your Roth.
You’d like to pay the taxes directly from Traditional and put the net amount in your Roth, but can’t do it that way and you shouldn’t try do that because you pay 10% penalty any distributions from Traditional before age 59½. (You have no penalty on the amount you convert-shift to Roth.) When you pay a penalty, you have thrown away some of your after-tax spending power for no good reason.
The correct way to convert is to pay the taxes from your prior Roth contribution basis. You owe no tax or penalty when you distribute Roth contribution basis.
Transfer $100 from your Traditional IRA to your Roth IRA; distribute $22 of prior contribution basis from your Roth but withhold it all for taxes. The $100 winds up as net increase of $78 in your Roth IRA. That’s what you want. (Later – there is a “five-year” aging period – you can pay tax on another conversion from your $100 conversion basis. It’s simpler after age 59½; there is no aging period on conversions.)

== Not apples to apples ==
Paying tax with “outside funds” – paying tax from your taxable account isn’t an apples-to-apples conversion. You are actually adding to your Roth.
Start with $100 in a Traditional IRA and pay the $22 tax out from cash in your bank account or from of sales of securities in your investment account . (That’s painful for most folks.) You wind up with $100 in your Roth IRA. You’ve effectively added $22 to your Roth. That’s good: you have more growing tax-free, but it’s not an apples-to-apples conversion.
Conclusion: I assume you’ve saved and invested well. If you have too much in Traditional IRA, you run the risk of paying surcharges to your Medicare Part B and Part D premiums after you’ve retired. Surcharges can add to $10,000s in retirement.
You ALWAYS want to convert Traditional to Roth if you stay in the 22% marginal tax bracket. You will never pay less than 22% on your topmost distributions from Traditional, and you ALWAYS lower the chances of paying IRMAA, because you have no taxable income when you distribute from Roth. “This widely touted retirement move IS all it’s made out to be.”
You get the correct apples-to-apples amount to your Roth when you pay the taxes out of prior contribution basis in your Roth before age 59½. (It’s much simpler after age 59½.) Paying added taxes with “outside funds” – from current income or from sales of securities from your investment account – is painful and doesn’t result in an apples-to-apples conversion.

































