[Thorrez]

If I give to a charity, I get a tax deduction. If I give directly to a homeless person, I don't.

Let's say my marginal tax rate is 50%. That means I could give $10 to a homeless person, or $20 to a homeless shelter, both costing me the same amount.

If someone has highly appreciated stock that is going to be sold, can donate it (e.g. through a DAF), and has the highest possible marginal tax rate in California, that person has the choice to donate $10 to a homeless person or ~$80 to a homeless shelter, both costing the same amount.