Professional jockeys are always seeking ways to gain the advantage over their riding rivals. Precisely how the jockey is positioned on the horse turns out to be an extremely important factor – one that has aroused recent scientific interest. One innovation is the so-called monkey crouch. This crouched style over the base of the horse’s neck was actually a drastic departure from the upright riding style that was in vogue until the very end of the nineteenth century. Who began this practice? Was this innovation the result of intelligent design? The answers to these questions vary, with three likely originators coming to the fore: Tod Sloan, Willie Simms, and Harding Cox. Their fascinating stories intersect in England and reveal that the invention of the monkey crouch was not due to foresighted design. The evolutionary processes of variation, selection, and retention seem to have been hard at work in its development.