First, some background.
Suppose you have some money with which you can do one of the following:
1) Pay taxes on it, put it (all) in a Roth IRA, and leave it there until you can withdraw it without penalty. 2) Don't pay taxes on it, put it (all) in a traditional IRA, and leave it there until you can withdraw it without penalty.Assuming that you withdraw it at the same time in case (1) and (2), it should be clear that which of these alternatives is better depends entirely on whether your marginal tax rate is lower when you deposit the money or when you withdraw it.
Now consider alternative (3):
3) Pay taxes on it and put it all in a taxable investment account.Assuming you don't want to touch the money until you would have been able to withdraw it without penalty from an IRA. Then it is clear that (3) is worse than (1), because you start out with the same principal either way, but you pay taxes on the earnings in (3) and not in (1). (3) might be better than (2) if your marginal tax rate goes up enough before it's time to withdraw the money, but (3) is definitely worse than (1).
Now for the real problem. Suppose you have some money on which you have already paid taxes, and you can do one of the following with it. In all cases we will assume that the money will stay put until it can be withdrawn without penalty:
1) Put it in a Roth IRA. 2) Put it in a traditional IRA. 3) Put it in a taxable account.Again it should be clear that (1) beats (3). But now (2) has a disadvantage over (3) that it did not have before: In (3), your earnings can potentially be taxed at reduced capital-gains or dividend rates, but in (2) they are taxed as ordinary income.
On the other hand, (2) has an advantage over (3): You don't pay any taxes at all on your earnings until you withdraw them.
So which is better, (2) or (3)? My back-of-envelope calculations suggest that (3) wins unless you plan to leave the money there for 15 years or more; but I wonder if anyone has a more detailed rule of thumb.
Lest you say that this situation is hypothetical, consider a 401(k) rollover in which there are significant after-tax contributions. If I understand the regulations correctly, when you do the rollover you have the choice as to whether to put the after-tax money in an IRA or take it as cash. In other words, for that money, you have a choice between (2) and (3). You do *not* have a choice of (1). That is, there is no way to roll the after-tax portion of a 401(k) into a Roth IRA. Would that there were!
So without that option, is there an easy way to determine which alternative makes more sense? So far, I think the answer is no; but I would welcome additional insight.