Last time I checked, donations to charity are only deductible IF you itemize (which means you don’t get to use the standard deduction, it’s an either-or-not-both kinda thing) AND only deductible up to 50% of your Adjusted Gross Income. A huge donation can cut your taxes approximately by half, perhaps two thirds, but won’t get you to zero.
Example: You earned $40,000 minus one $4,000 exemption gives you an AGI of $36,000. You have $1,500 in deductions, so you take the standard deduction of $6,000 instead. Hence, you owe taxes on $30,000, which comes to about $4,000. But if you donate to charity something big which, by some miracle, you convince the IRS that it’s worth millions even though you only paid a few grand for it, then you can deduct $18,000 that year (50% of your AGI) plus your $1,500 other deductions, so you owe taxes on $16,500, which comes to about $2,000. Basically, you cut your tax bill in half. Your tax bill is NOT zero.
You also have to calculate the Alternative Minimum Tax and see if that’s more. The only way this works out to you owing zero dollars for income tax is if (a) you had lots of other deductions such as excessive medical bills and mortgage interest, or (b) you had lots of tax credits such as the Earned Income Tax Credit.
There are cautionary tales about people who won huge prizes and said “Eh, I’ll just donate the whole thing to charity” and ended up owing more taxes than they could ever pay. If you win a million dollars at a casino and give all the money to charity, you basically end up owing taxes on about half a million dollars, somewhere in the neighborhood of $200,000 debt. And it never goes away, even if you declare bankruptcy.
However, the story about the MIT guy uses the word “loss” in quote marks. Donations and losses aren’t the same thing. Losses aren’t subject to the 50% AGI rule, but they are subject to a whole bunch of other rules. I say this story sounds very fishy. Like when you hear a second-hand story about a 400 lb fish that was caught in Lake Tahoe-- yes there was a fish, yes there was a boat, yes a person on the boat caught a fish, NO it did not weight 400 lb, and NO it wasn’t true that they never had to buy groceries again. I rate this story as “partly true, likely embellished”.
And, if you have a windfall and you want to donate it to charity, consult a tax attorney first. IANAL