The 1993 inaugural issue of the "Journal of Statistics Education" ("JSE") published an article about a small conference for Principal Investigators (PIs) and co-PIs of twelve projects in statistics education funded by the National Science Foundation (NSF). This twenty-year retrospective (1) offers some personal memories related to the founding of "JSE," (2) offers some thoughts about the legacies of the twelve funded projects, (3) sets out a sense of how the conference themes have fared over the last twenty years, and (4) indicates what this might suggest about the future of our profession. In conclusion, I argue (briefly) that at this moment in its history, statistics education faces the biggest opportunity and challenge of its last 40 years.