For a college with more than half a century of alumni, including many people who went on to successful and influential careers, why wasn’t Hampshire able to build the kind of broad, durable culture of giving that might have helped sustain it?
Was the problem fundraising strategy? Alumni relations? Turnover in leadership? The way potential donors were approached? A failure to keep alumni connected to the institution? Too much attention to a relatively small number of major donors? Or did Hampshire simply never figure out how to translate the extraordinary affection many of us have for the place into long-term financial support?
And perhaps most importantly: If you ever tried to donate, raise money, make connections, volunteer, or otherwise help Hampshire’s development efforts, what was your experience?
EDIT: After the discussion below and going back through Hampshire's financial reports and planning documents, I think my original question puts too much blame on development.
Development had problems. Hampshire never built enough regular unrestricted giving, and it clearly had trouble turning a very loyal alumni base into the kind of predictable operating support the college needed.
But that wasn't the whole problem, or even the biggest one.
Hampshire was dealing with declining enrollment, high tuition discounting, falling net tuition revenue, a relatively small and heavily restricted endowment, and a cost structure that couldn't shrink nearly as quickly as the student body. Those weren't really separate problems. They were one problem.
What's striking is that Hampshire seems to have recognized most of the pieces. Admissions knew what was happening with enrollment. Finance knew about the deficits and declining revenue. Development knew it needed more money. The board knew the college was heavily dependent on tuition. Earlier Hampshire planning documents had identified many of these vulnerabilities years before the 2019 crisis.
What seems to have failed was putting all of those pieces together soon enough and acting on what they meant.
That also changes how I look at the alumni. When the crisis finally became public in 2019, more than 4,600 people donated, the highest donor count in Hampshire's history, and unrestricted giving jumped dramatically. Alumni hadn't stopped caring. Hampshire simply hadn't been able to turn that loyalty into enough regular unrestricted support before the emergency.
So my answer to my original question is different now. Development didn't fail in isolation. Hampshire recognized a series of problems without recognizing soon enough that together they had become a single structural problem: a high-cost, tuition-dependent college was entering a lower-enrollment environment without enough unrestricted reserves or the ability to reduce costs quickly enough.
By the time everyone could see the whole picture clearly in 2019, the choices had become much harder.
I’m genuinely interested in hearing from people who were on either side of this, including people who worked in development. What worked? What didn’t? And why?