Edgar Anderson of the Missouri Botanical Garden had long and rich collaborations with such mathematicians and mathematically inclined biologists as R. A. Fisher, Sewall Wright, and John Tukey. It was Anderson’s Iris data that Fisher used to develop his linear discriminant function to capture multiple variations. A sabbatical with Wright in 1933 helped hone Anderson’s mathematical skills while helping him understand what mathematics could and could not do. He and Tukey shared an interest in conveying data graphically. This long-standing commitment to applying mathematics to natural history problems informed his scientific career as he sought to capture the variations he recognized in the natural populations. He used graphical tools to examine hybridization as an evolutionary mechanism and to use the taxonomic data from these variations to study the underlying genetic forces at work in evolution. In important synthesis articles in the mid-1950s, he summarized his conclusions about applied mathematics and natural history. They were not mere technical tools, but reflected a commitment to observation and pattern recognition as the basis of his science. Understanding these views more fully deepens an appreciation of this constantly independent-minded contributor to evolutionary theory in the twentieth century.