Kappa Sigma traces its roots back to the year 1400, in Bologna, Italy. Bologna was renown throughout the Western world for its University, the University of Bologna. Bologna has been home to some of the greatest thinkers of all time, including Dante, Petrarch, Galileo, Copernicus, and many others that contributed to its academic reputation. During this time, the students of Bologna were terrorized by the unscrupulous governor, Baldassarre Cossa. Cossa and his followers would lay in waiting on dark streets to rob students. Manuel Chrysoloras, a teacher of language at the University, helped the students form a society for mutual protection against Cossa and his robbers. These students devised secret signs, words, and forms - a ritual, to protect themselves from Cossa's spies and henchmen. It was this ritual that bound them as brothers in fellowship, the fellowship that would become Kappa Sigma.

The Order of Kappa Sigma expanded to many other great European universities throughout the Renaissance, but by the 19th century, it was barely active. In the mid-1800s, an American traveling in Europe was given the secrets of this order, and from this, Kappa Sigma in North America was born.

Kappa Sigma in America was founded one chilly evening in the fall of 1869, as five students attending the University of Virginia, in Charlottesville, gathered in William Grigsby McCormick's room at 46 East Lawn and planted the seed of Brotherhood. For many weeks the bonds of friendship had drawn these five together; now the need became clear for a formal structure to contain their feelings. Thus, not only did these Five Friends and Brothers formalize their friendship, but they also created a Fraternity steeped in the traditions of the past. The new Brothers recorded their bond in a Constitution and an Oath, which set forth the ideals and principles to all Kappa Sigmas today.

From these humble origins, the Order of Kappa Sigma has come to dominate the fraternal world, and is the largest and most successful fraternity in North America.