The development of electrostatic rotating machines for macroscale power conversion has been largely sidestepped, given the uncertainty of its capabilities and place in the technological hierarchy. This article reviews prior and present works in macroscale electrostatic rotating machinery and identifies the relevant machine types, their limitations, and strategies for performance improvement. The separately excited synchronous electrostatic machine presents the greatest opportunity for competitive macroscale category-two machinery, and a strategy of multiplicative gains is established. The strategy spans machine modeling, optimization, gap media (gases, liquids, and vacuum), gap maintenance, advanced manufacturing techniques, and power electronic drives/control. Ultimately, the product of innovation gains across all these areas reveals that macroscale electrostatic machinery is possible and potentially competitive with magnetic machinery for specific areas, including position and hold, low-speed direct drive, and high-voltage utility generation applications.