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Been playing with a spreadsheet about this. Using a somewhat unrealistic model (all gains long term, but all stock sold yearly), I find that in the long run, the IRA always beats paying the capital gains tax for realistic rates of return. However, "long run" might be too long for many people: For a 10% rate of return, 39.6% bracket, nondeductible IRA, it's over 30 years before the IRA takes the lead.

The higher the rate of return, the sooner the IRA takes the lead.
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