Among the most provocative passages in Niccolò Machiavelli’s The Prince is his discussion of whether it is better for a political leader to be loved or feared by his or her subjects. Machiavelli argues that political stability and effective governance are more readily achieved if the people fear, rather than love, their political leaders. Noting that Machiavelli rarely cites biblical texts to demonstrate the wisdom of his counsel, this study begins with the question of whether he could have found illustrative examples of this position in the Hebrew Bible. I then ask a broader question about whether the presence of such examples would demonstrate a more fundamental agreement between the Hebrew Bible and Machiavelli on the topics of fear, love, and leadership. I examine primarily narrative materials, finding examples of leaders who successfully wield fear to enhance their authority, namely, Moses, Samuel, Joshua, and Solomon. In addition, Saul represents the exception that proves Machiavelli’s rule, and David supports his claim that the people’s love is fickle and, if unaccompanied by fear, can result in political chaos. I conclude by acknowledging a reluctance to commend fearing a leader especially in biblical legal texts, which instead promote fearing YHWH; but ultimately the evidence points to a substantial agreement between the Hebrew Bible and Machiavelli that the people’s fear of their leader promotes national stability and affirms a leader’s authority.