Like most middle class families after the 2018 tax code changes, even with a mortgage I'm very far from being able to itemize. Looking at how to optimally give to charity, it seems like a shame to not be able to give 20-30% more just from tax deductions.
I then considered a potential loophole. If I give a sum of money less than the $15,000 tax free gift limit to a trustworthy high-income friend who already itemizes, that person can then donate the money to charity. In addition, he or she could also donate the amount it saved them on their taxes. The net result would be that the charity gets more money.
I'm skeptical that I've somehow beaten the system, but I'm not sure where this would cause problems. I'm not getting consideration in return for the gift; it's just going to a charitable organization, and not even in my name.
I understand the potential for abuse, since the "trustworthy friend" could just pocket the money, but my question is whether I'll run afoul of the IRS doing this, not whether this is a good idea.
Another approach to being able to deduct charitable giving is to save up for many years and give all the money in one year in order to get a tax deduction. The give-to-a-high-income-individual approach results much more money for charity, consider a simple example. Someone making $80,000 per year with $10,000 in itemized deductions in a given year might save up $50,000 and donate all that money to charity in a given year. That would reduce their taxable income by roughly $48,000 relative to that standard deduction. This saves them an additional roughly $10,000 to give to charity based on a simple calculation here. Giving the 50,000 to a high income individual (over many years instead of saving for one year) lets that individual deduct the money at a high marginal tax rate. At a 35% tax rate that would save an additional $17,500 to donate to charity. And just donating it each year without saving and donating on one year would result in $0 extra for charity.