Philanthropy Daily’s weekly columnist, Martin Morse Wooster, has done the philanthropic world a formidable service with the publication of How Great Philanthropists Failed and How You Can Succeed at Protecting Your Legacy. The book is an expanded fourth edition of his earlier work, The Great Philanthropists and the Problem of “Donor Intent.”

In Part I of his book, “Undermining Donor Intent,” Wooster takes the reader through nine significant historical instances in which charitable legacies veered from the intentions of their founder or took on a life of their own under new leadership.

The examples range from the tragic—renunciations of leadership in the face of public pressure—to the avoidable—mission creep due to the founder’s inability to offer clear guidelines on future grantmaking.

A couple of common themes run through the stories recounted by Wooster.

First, we realize the consistent damage done to donor intent by the simple extension of a philanthropic legacy beyond the death of the original donor. Any reader who takes up Wooster’s book not just out of historical curiosity but as a practical lesson in how to manage their own philanthropic legacy may be strongly tempted to give away all of their wealth during their lifetime.

Short of that, they will strongly consider setting a sunset date by which all funds will be disbursed, preferably within one generation of their death. In all of Wooster’s examples, we see a constant tendency of foundation managers to embrace a very different philosophy of giving from that of their founders.

Second is the seemingly unavoidable tendency towards the bureaucratization of large philanthropic legacies. Almost inevitably, foundations attract to themselves cadres of experts and managers who professionalize charitable giving.

The professionalization of philanthropy has the consequence of making giving less properly charitable and more systematic. At first glance, this seems like a good thing: imposing order and systems on scattershot charitable giving promises to make philanthropy more effective, offering more bang for the philanthropic buck.

But systematization also makes philanthropy abstract. Donors who found philanthropic foundations tend to give based on their personal attachments. They make gifts based on their personal philosophies and in response to the people, places, and causes they know personally. This gives philanthropic charity quirkiness and character. Each person is unique, and the causes we grow to love in our lives (and therefore give to) are in a sense uniquely and irreplaceably our own. The best program of donor intent would seek to define the characteristics that most accurately define the founder’s quirkiness and extend those into the future.

But when professionalization takes hold of foundations, the historical record—as Wooster makes clear—shows how quickly they become generic. Rather than reflect the personalities and interests of their founders, they become subject to ideologization and begin advancing politically and socially fashionable causes.

Many large foundations today are no more than bellwether institutions for establishment thinking. It is unclear whether systems-level, “generic philanthropy” of this sort really becomes more effective at all, or whether it merely serves to reinforce outmoded agendas long after they have ceased to hold credibility.

The tragedy in Wooster’s examples of donor intent gone wrong is that donors themselves often planted the seed of their legacy’s undoing.

The chapter on John D. Rockefeller’s legacy is absolutely painful to read as we see the tycoon slowly separate himself from the destiny of his philanthropic legacy, rationalizing himself into a false humility due to sustained public criticism.

The chapter on John D. MacArthur shows what happens when a donor is more concerned about where his money shouldn’t end up than where it does. In Wooster’s words, “MacArthur did not wish to leave his fortune to his children and he was also concerned about estate taxes. So he quietly decided to leave his wealth to two foundations.”

But rather than define a mission, or some positive vision of how his money might be used, MacArthur insisted on intent agnosticism, saying, “I’ve seen too many people, including Henry Ford, try to administer their estates from the grave. You have changing times. Besides, you lay down rules and people don’t follow them. So, I’ll trust in the Almighty that my trustees will do more good for the country than I would.” It is hard to see how MacArthur could not envision a scenario in which the professional successors of his legacy would define “good for the country” along lines completely contrary to his own convictions.

It is that sense of tragedy in all of Wooster’s examples that makes Part I of his book such satisfying reading, whether for the philanthropist reflecting on the form their legacy ought to take or for the student of philanthropic history.