This chapter provides a comprehensive cultural and mathematical history of the wheat and chessboard problem—a classic tale involving exponential growth across a chessboard. Tracing its origins from ancient Babylonian mathematics through Arabic, Persian, Greek, Latin, Romance, and Germanic sources, the chapter examines the problem’s evolution across diverse civilizations and intellectual traditions. Through new textual evidence and a comparative lens, this chapter repositions the wheat and chessboard problem as a significant epistemic and cultural node in the global history of knowledge. Emphasizing newly discovered Byzantine Greek sources alongside better-known Arabic and Western ones, the chapter reveals how the problem served not only as a mathematical puzzle but also as a vehicle for exploring philosophical, cosmological, and financial questions. The problem is analyzed not only as a computational exercise but also as an epistemic object: a story-structure that encodes fundamental ideas about scale, growth, visualization, and value. Special attention is given to methods of representing and visualizing the staggering outcome of 264 − 1, as well as to the conversions of units across cultural contexts. The chapter argues that the wheat and chessboard problem functions as a cultural fil rouge connecting historiography, recreational mathematics, number theory, and early modern accounting, reflecting the cross-pollination of science, literature, and economics in premodern thought.