Johann Von Staupitz had no idea what he was getting into when he first met Martin Luther in 1506. Luther had recently left his legal studies at the University of Erfurt to embrace a life of monastic rigor in the Augustinian monastery. He brought with him a deepening spiritual crisis that would pose a challenge for Staupitz in his role as mentor and personal confessor. Staupitz had been elected Vicar General of the German Augustinians in 1503 and earned a doctorate in theology in 1500. He had the requisite spiritual and theological qualifications to deal with complex spiritual struggles. And, yet, his new charge would tax his considerable abilities to the limit.

Luther felt compelled to share his every sin when it came to the confessional. The comprehensive breadth of Luther’s confessions was reported to rival that of his order’s famous namesake, St. Augustine of Hippo. Luther reported years later that he had once kept Staupitz in the confessional for six hours as he labored to ease his troubled conscience. Staupitz joked that Luther confessed for hours on end without confessing “anything interesting.” Things got very interesting when Staupitz challenged Luther to just let go of his guilt and love God. “Love God!” the future Reformer responded, “I hate God!”

Staupitz’s response to this bit of blasphemy had the potential to make a tremendous difference in Luther’s life. He could have rejected his young charge. Staupitz could have reprimanded him. It would have been easy to abandon Luther to his struggles. Would it not have been much simpler to explain the failure of this promising monk as a poor fit with the monastic life? Staupitz knew that such an explanation would not suffice. Luther showed every mark of superior progress in his work, devotional practice, and obedience to the order. It was in fact because of his pursuit of excellence and spiritual purity that Luther was plagued by such inner turmoil....