Ok if I can't put them directly into my roth couldn't I bend the rules a bit? Wouldn't I be better off in the long run if I took the extra $1400 that I have available to me in my roth annually and slowly liquidated and then rolled the cash into the roth and just re-purchased the same stock? Wouldn't I be paying a small price now on commission to my broker to save alot later on capitol gains?

I gather the $1400 you're talking about is your remaining allowable annual contribution, beyond the current $50/month? If what you're suggesting is selling stock X (in your regular brokerage acct), paying capital gains (if needed), then putting the proceeds (in cash) into your Roth account and buying the same stock X - sure, you can do that, and it's not bending the rules at all. Though if in fact you have a loss in your position, watch out for a wash sale if you buy the same stock in your IRA. And note that all this is assuming that you have sufficient earned income to make the annual $2000 contribution. As for the wisdom of moving the stock into the Roth so as to avoid capital gains down the road, time will tell. It all depends on how well your stock does - you seem pretty darn certain that you'll have mucho profit in 40 years!

Ohh, and how can capitol gains not be such a bad thing. It is the worst tax ever concieved!

I'm not crazy about capital gains taxes myself. What I meant was that it's a Good Thing to have a gain. If you buy X and sell it 20 years later, two things can happen - a gain or a loss. What I meant is that a gain is a heckuva lot better, even if you have to give some of it to Uncle Sam. <Rant>It drives me crazy when someone writes (on these boards, or in the newspaper, wherever) that they have capital gains of $200,000 on such and such a transaction, and how can they avoid paying tax? Well, get over it! Pay the damn tax and be glad that you have such a nice gain! Lots of people would be happy to have this kind of problem.</Rant>

Lorenzo2