In this article, I present two virtually unknown sixteenth-century views of human freedom, that is, the views of Bartolomaeus de Usingen (1465–1532) and Jodocus Trutfetter (1460–1519) on the one hand and John Mair (1470–1550) on the other. Their views serve as a natural context and partial background to the more famous debate on human freedom between Martin Luther (1483–1556) and Erasmus of Rotterdam (1466–1536) from 1524–1526. Usingen and Trutfetter were Luther’s philosophy teachers in Erfurt. In a passage from Book III of John Mair’s commentary on Aristotle’s Nicomachean Ethics from 1530, he seems to defend a view of human freedom by which we can will evil for the sake of evil. Very few thinkers in the history of philosophy have defended such a view. The most famous medieval thinker to do so is William Ockham (1288–1347). To illustrate how radical this view is, I place him in the historical context of such thinkers as Plato, Augustine, Buridan, and Descartes.