Ever heard of Zope? Ever heard of it recently? Being a leader, then not, in a large open source project over a long period of time generates a lot of funny stories. And mistakes. And even, moments of wonder, not always intentionally. In this talk I'll cover a number of insider stories from the life of Zope and Plone, then analyze them from the safety of perspective. The long view can help show what makes a big project vary in success over time measured in decades. I will also include stories and lessons from long-running, successful leaders in other Python projects.