After being disbarred from practicing law for having less than legitimate credentials, Jeff Winger enrolled at Greendale to get the education that he needed. He graduated after four years and then failed at another attempt at law. This lead to him being brought on as faculty during the fifth season. Jeff spent much of his education in blow-off courses so it was only fitting that he became the teacher of a blow-off course himself. A recent episode had a prison inmate enrolling in Jeff's class via video networking through an iPad. Jeff explained to the new student that he would teach him a thing or two. "And I literally mean a thing or two," Jeff reiterated. The jailed student would then complain as Jeff tried to pass the class time by showing a DVD of the "Planet Earth" documentary because even inmates do not always understand a good thing when they see it. Jeff would later try to murder this student, sort of.
