QUOTE (Sieve @ Nov 15 2008, 08:43 PM)

You aren't reducing the taxes when you put the one IRA (with 100% deductible contributions) into a 401(k) plan before converting the other IRA to a Roth, because eventually the 401(k) will have to be distributed and tax paid on the entire amount. Bottom line is that you will have to pay tax on all deductible IRA contributions at some point in time whether as a result of distributions from the IRA, or a conversion to a Roth, or distributions of the rolled-over IRA when it comes out of the 401(k)--so, to me, the real issue is how much of the IRA you want to convert. Maybe you've already made that decision.
I'm also wondering if you can directly transfer from an IRA to a qualified plan other than pro-rata as to basis (i.e., deductible vs. non-deductible). Seems to me that since a traditional rollover is considered a pro-rata distribution of deductible & non-deductible contributions, that a direct transfer rollover should be the same.
Sieve,
My wife and I are in 59 +/- 1 years old. Our hope is to wait until 70 before tapping Social Security. In the mean time we hope to convert a lot of tax-deferred money to Roth IRAs. When we tap into SS, we can shelter that SS income from taxes by drawing down the Roths (assuming that we have managed to minimize RMDs by depleting tax-deferred accounts in the interim). I agree that we will ultimately pay taxes on the 401k money but believe that we are better off postponing tax payments... other than those on the Roth conversions.
It is my understanding that you can move untaxed money from IRA accounts to a 401k and leave the post-tax money behind for conversion to a Roth IRA, thereby minimizing
current tax liability.
Thanks for taking time to comment.
Michael