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In other words, if I have a capital gain of $100,000 and I give $25,000 to charity, can I deduct this from the capital gain so that I am only taxed on $75,000? Or are you only allowed to deduct from ordinary income?

If you're planning to give $25K to charity, and you still think the investment is a good investment, I'd probably wait until I had significant income, and then give the appreciated stock. (there is no capital gains on donated stock)
At least I'm *assuming* that you're going to have significant income in a year or 3.

Even if you don't want to wait, I'd still plan on giving the appreciated stock to the charity. It'll mean a little delay (3-5 business days in my experience) from when you tell your brokerage to transfer it to when they actually do the transfer. And that means the $ amount donated is not under your control completely.

I'll let the experts address the questions you posed. (my expectation is cap gains income is still income)
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