[Question] How to make the most impactful donation, in terms of taxes?

Hi, this is my first time post­ing.

I want to start donat­ing 10% of my in­come to char­ity. How­ever, this would be about $10,000 a year—i.e. just un­der the stan­dard de­duc­tion, such that none of it would be tax de­ductible. This seems ridicu­lously in­effi­cient. I could be some­what more effi­cient by clump­ing my dona­tions—e.g. donate $30,000 per 3 years, and get $18,000 of it tax ex­empt. But I want to do bet­ter.

My dad item­izes his taxes and is in a higher tax bracket than me (50% in­come tax). If he were to donate $20,000, he’d get $10,000 back on his tax re­turn. So if I gave my dad $10,000 and he donated it, my dona­tion would be liter­ally twice as im­pact­ful as if I did it my­self.

The ques­tion is, are there any le­gal is­sues with this?

  • Giv­ing the money to my dad: I know that the gift ex­emp­tion is $15,000, so I could give my dad up to that with­out ei­ther of us not­ing it on our taxes. I do want him to do some­thing in par­tic­u­lar with the money—is there any way that could cause it to not be con­sid­ered a gift? It seems like in prac­tice, many things things that would fall un­der the gift ex­emp­tion do come with ex­pec­ta­tions (e.g. a par­ent giv­ing their child money they in­tend the child to use for rent).

  • My dad writ­ing the dona­tion off: Would there be any­thing pre­vent­ing my dad from writ­ing the dona­tion on his taxes? There’s some­thing about how if you make a char­ity dona­tion, you’re not sup­posed to write it off if you re­ceive or ex­pect to re­ceive a benefit from it. I’m not sure if this means “from the char­ity” or “from any­one” though. (It’s also un­clear my dad would be re­ceiv­ing any benefit, be­cause this is dol­lar-neu­tral for him). Another ex­am­ple that this can’t too literal—I imag­ine some EA might want to take their new EA friends out for din­ner to cel­e­brate them start­ing the Giv­ing What We Can pledge—that seems like it shouldn’t nega­tively af­fect any­one’s taxes.

  • What if my friends also want to max­i­mize their dona­tions by rout­ing them through my dad? Is any­thing differ­ent be­cause they aren’t fam­ily mem­bers do­ing the giv­ing? No one in­volved would be writ­ing any le­gal con­tracts or any­thing.

Thanks in ad­vance for any ad­vice! I know taxes are bor­ing for ev­ery­one, but I don’t want to miss the op­por­tu­nity to make my dona­tions more effec­tive.

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