So yes, in this case, it didn't work out for the general public. That indicates no intention of wrongdoing, nor does it indicate that the system is broken. Equity values on the whole tend to rise over time, which means that charitable stock gifts overall (especially those that are held for long periods of time) are actually better for the public than cash donations.
It's not about wanting the stock to do poorly; as the chief executive, he knows where he plans to go with the company, and if he doesn't see it going far, then at least he can save some money. The fact that investors interpreted the move this way indicates that it's not about hindsight, but a poor forecast.
Your point about values rising on average is a good one though - it means that though some of the rich may be getting away with more money, overall donations are still going to balance that. There are still some other issues though.
Investors appear not to have interpreted it that way. That interpretation was disingenuously rendered by this article’s author in support of his premise for it. See [1].
Of course the main reason for that is other parts of the tax code, not DAFs. But I think DAFs get targeted for criticism because they make it a lot easier to exploit these kinds of flaws.
I'm not entirely sure you can, based on my reading of 26 CFR 1.170A-1(c)(3) [1]:
> (3) If a donor makes a charitable contribution of property, such as stock in trade, at a time when he could not reasonably have been expected to realize its usual selling price, the value of the gift is not the usual selling price but is the amount for which the quantity of property contributed would have been sold by the donor at the time of the contribution.
"...[Mr. Woodman] was giving away much of that wealth — some $500 million worth of GoPro stock — to the Silicon Valley Community Foundation...Mr. Woodman avoided paying capital gains taxes on that $500 million worth of stock, a figure that most likely would have been in the tens of millions of dollars..."
Of course he avoided capital gains on the stock he gave away - he couldn't sell it anymore because it was no longer his. The entire section about Nick Woodman strives to imply that something improper has occurred, but all I see is a successful entrepreneur that gave away a large part of his fortune. Regardless of how long it takes for that money to be distributed by the charitable fund, the money is forever no longer his.