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by coredog64 16 hours ago
> taxation of stock buybacks (which is a way to pay dividends without paying income tax on them

I don't think you've got the mechanism correct here. If a corporation has cash, they can pay dividends which lands in the pocket of every shareholder equally. Or they can buy those shares back from shareholders who are willing to cash in. If I hold shares and don't sell in the face of a buyback, I'm not getting a dividend. Instead, my on-paper wealth has increased by the amount that the buyback juiced the price of my shares. If I do sell, then I pay short term capital gains (which are effectively the same rate as income tax) or long term capital gains (which are lower but probably not low enough to offset the extra tax created by inflation)

1 comments

No, I know exactly how the mechanism works. Right now if you get a dividend and reinvest in the stock, you pay income taxes, then you pay capital gains on the stock you buy with those dividends, albeit at a higher cost basis. Both buybacks and dividends are a means of transferring wealth to an investor, and buybacks are used because they are tax advantaged for investors, and investors like that.

It’s easier to “avoid” capital gains than it is to “avoid” income taxes by using things like trusts, borrowing against the stock, changing tax residency etc. Those loopholes should all be closed too, obviously, but a stock buyback is effectively a dividend under another name. It could be taxed that way if we wanted to do it. Then you’re taxing the wealth at source rather than trying to trace billionaires’ wealth around the world.