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I clicked on this article since I know of a good example of a donor making things complicated and half-expected to see it here. When I rented my current NYC apartment in 2012, I googled my landlord, a man named Paul Bogoni, and found this atop the search results: https://law.justia.com/cases/new-york/appellate-division-fir...

The cases in the article don't quite approach this magnitude of conflict — what do you do when a donor defaults on a pledge? What do you do when a donor sues you because they're unhappy with how you spent their money?

>> what do you do when a donor defaults on a pledge? What do you do when a donor sues you because they're unhappy with how you spent their money?

Talk to a lawyer. Sometimes pledges are just empty promises. Sometimes they are actually contracts. The former can be ignored. The later must be handled by legal professionals.

Examples:

I promise to give you $100 = nothing. I promise to match donations up to $100 = contract. I promise to leave you $100 in my will = nothing. Let my kid hang a painting in your gallery and get $100 in my will = contract.

The use of famous names can be tricky irrespective of whether they once donated or not. "The Micheal Jackson school of dance" ... expect lawyers. "The Trump memorial outhouse" = free speech ... also expect lawyers but feel good that you are in the right.

> I promise to match donations up to $100 = contract.

Hm? Where's the consideration for me? Doesn't a contract require consideration on both sides?

You have to engage in whatever fundraising efforts are necessary to obtain the first $100.

In this case, we both value progress in the philanthropic endeavor, so we make a contract: "if you generate $100 of investment in the endeavor for me, then I will invest $100 in the endeavor for you."

I am pretty confident such a contract would be legally defective and unenforceable in those terms. You raising money for yourself is not consideration that I receive, regardless of whether I think it's a good thing.
IANAL, but Promissory Estoppel might apply here?
The contract is also between the donor and other donors that give on the belief that thier donations will be matched. Because of the promise (offer) they do something they otherwise would do (consideration). And they accept by giving the money.
"Complicated" in this case consistently means "wanting their gift to be used for their ends rather than the institution's internal ends". Most of the solutions are "well, you should have a policy". What is a "policy"? It's a way to claim the institution has tied itself to the mast and can't possibly change its decisionmaking process.

The entire article is a giant warning sign to donors that there is an apparatus devoted to, eg, swindling boomers with fond memories of college football into financing Maoist campus struggle sessions.

I am not sure why wealthy people donate to universities run by maxists.
As someone who transitioned from IT management to alumni relations/fundraising at an NFP, I've experienced a couple of these 'complications'- they crop up in all sorts of ways.

A couple of examples:

1. Donor (decades ago) created a scholarship for boys from his old school (boys schools) to come and study at my institution. However, since then, the school has become co-ed and we now get the occasional situation when no boys apply, but we have exceptional female students applying. The trust which controls the scholarship will not allow us to award the scholarship to females as that will contravene the will.

2. We had one recently deceased donor donate $10k in her will for daffodils for our grounds. Our grounds are not that large nor are there many suitable places for the daffodils - eek! Luckily we were able to discuss the issue with her daughter and modified the request to become some memorial benches and daffodils.

Then the trust is being bone-headed. The legal system is full of such issues. There were/are countless laws that refer to males by default (ie "The defendant shall submit his notice.") Where such rules have yet to be rewritten they are treated as gender-neutral. My advice would be to submit such applications as "the graduate from the school" and leave it to the trust to reject them. Leave the box unticked. The trust will then be risking legal challenge when they demand that a child identify itself as either male or female.

Remind the trust that it will be much easier to make things gender neutral today than have to deal with the inevitable female applicant who self-identifies as a boy. Such people tend to fight these things. And more power to them.

Risking legal challenge from whom, and under what law? Private scholarships are not equal opportunity.

Also, do you think that fighting with the trust of a deceased or elderly donor is a good idea, for somebody in the business of asking wealthy people for donations? It is definitely not.

Well, I don't know your particular jurisdiction, but many have come to see such wills as against public policy. That can make them unenforceable. So the estate might not be able to come after the school, but the specific mechanism will depend entirely on how the scholarship was setup.

>>An Ontario judge has struck down a deceased doctor’s attempt to set up university scholarships exclusively for white, single and heterosexual student. [...] Her decision invoked a little-known legal principle — stemming from an 80-year-old Supreme Court of Canada judgment — that allows courts to quash people’s final wishes if they clearly offend the interests of the state.

https://nationalpost.com/news/canada/ontario-judge-overturns...

While US courts still tolerate race and gender-based discrimination in wills invoking close family members (ie "my son only inherits if he marries a Jewish girl.") they are less tolerant of bequests held out to members of the public. "100$ to every non-black man in town" would be easily challenged. Specifying only "boys" is a step towards that line.

I still see the occasional land deed in my area with a "no chinamen" stipulation, but everyone knows to either ignore or erase such things.

Maybe you should just not award the scholarship altogether, if the funds cannot be allocated fairly.
Getting rid of scholarships that differentiate on gender, race, or religion on a national level would be a nice improvement to society. I suspect however that such change has very little political support.
Unless the entire year is female how can there situations where no boys apply? Are the boys not told about the existence of this scholarship?
Wills can lead to some fascinating outcomes. Here's one that I always enjoy:

Henry Trigg (c. 1667 – 6 October 1724) was an English grocer who became famous following his death for his eccentric will which had his body placed in a coffin in the rafters of his barn, which became a tourist attraction

https://en.wikipedia.org/wiki/Henry_Trigg_(testator)

It can be complicated the other way around, too.

I donate annually to a local high school in my mom's honour. It's for women in STEM. This was my first donation since the fund ran dry. I was so excited to give out the awards at commencement.

One young lady added it to her pile of other awards without a smile and the other didn't even show up despite being told they were receiving it.

It was really important to me and I inflated it so much in my mind so it's kind of my fault. Had a pretty good cry in the parking lot after just slipping away early.

It taught me how hard it can be to get a reward to the right person who needs it and deserves it. It also left me thinking about how picky can I be. Can I ask them to find people who aren't wealthy or already loaded with scholarships?