I love how philanthropy is such an intimate expression of personal values. Donors give to causes that uniquely move their hearts and minds–what lawyers call “donor intent.” As I have worked with donors over the years, I have been inspired by the wide range of people’s charitable affections, and how that variety meets so many important societal needs. Some gifts or bequests make me scratch my head…but I am mostly glad just to see people acting on their generous leanings.

Which brings me to Leona Helmsley. Never a sweetheart, when she ran a hotel chain the tabloids nicknamed her “The Queen of Mean.” During a tax evasion case, she once snarled, “Only little people pay taxes.” Nice or not, she died wealthy.

In 2007, she left around $5 billion to the Helmsley Charitable Trust, setting it up to be one of the wealthiest grant makers in the country. But consistent with her eccentric life, Ms. Helmsley also made eccentric trust provisions: she dictated that all of her estate should go to the care and welfare of dogs. To put the Helmsley Trust in perspective, a New York Times analysis estimated that the estate was worth almost ten times the amount of assets of all 7,381 animal-related nonprofit groups that reported to the IRS in 2005.

Now, I love dogs as much as the next person. My golden retriever Duke is one of my best jogging companions, often fitter and always cheerier than my human companions Don, Vernon and Dave. But I have seen enough needs in the US and around the world to conclude that the wellbeing of domesticated animals is a poor way to spend $5 billion.

Most everybody else, including the courts, thought that was a bad idea. There is a legal principle that allows courts to ignore illegal trust provisions, such as when money was left to build a nursing home for white patients only. The judge handling the Helmsley estate, however, never had to resort to that. Instead, he cited ambiguous Trust language in overruling Ms. Helmsley’s Trust and allowing the Trustees to distribute the money “in their sole discretion.” In the first round of distributions, the estate gave out $136 million, with only $1 million divided between ten animal and dog charities.

I admit to being conflicted, because I believe so strongly in donor intent–that a person should be able to give away money for legal means, as his or her heart leads. Even if the gift is controversial and has lots of zeroes after it.

In this case, I am contented because the courts have overruled a ridiculous estate plan made by The Queen of Mean. But next time, money might be diverted from a cause that is vital to me…albeit out of step with society. This especially concerns me as I see declining societal tolerance with some values I hold sacred. In the Helmsley case, I believe that the court laid waste to donor intent, and their decision is for the dogs.