Tom Walker entered into his contract with the devil willingly. He was driven to do so by greed and an unscrupulous nature. He rarely considered the thoughtlessness of his bargain until he began to grow old. As he faced his own mortality, Irving writes that Tom Walker “thought with regret on the bargain he had made with his black friend, and set his wits to work to cheat him out of the conditions. He became, therefore, all of a sudden, a violent church goer.” This is the first attempt to renounce his deal with the devil. He does not simply attend worship services, however. He employs a second strategy:
“He prayed loudly and strenuously as if heaven were to be taken by force of lungs. Indeed, one might always tell when he had sinned most during the week, by the clamour of his Sunday devotion.” In this instance, he seems to believe that the force of his repentant cries will be enough to erase the bargain that he has contracted with the devil.
Tom Walker’s fears grow more intense and he shifts his focus from his own pains to appear righteous to the sins of his neighbors:
“ Tom was as rigid in religious, as in money matters; he was a stern supervisor and censurer of his neighbours, and seemed to think every sin entered up to their account became a credit on his own side of the page. He even talked of the expediency of reviving the persecution of quakers and anabaptists. In a word, Tom's zeal became as notorious as his riches.” Here, he hopes that by censoring and condemning his neighbors for their sinful habits, he will gain salvation for himself.
The fourth step he takes in securing a release for himself is to superstitiously keep a bible on or near his person at all times. He hopes that the presence of the Holy Scriptures will ward off any attack from the devil. To protect himself, therefore, he kept a small bible in his pocket and another on his desk:
“Still, in spite of all this strenuous attention to forms, Tom had a lurking dread that the devil, after all, would have his due. That he might not be taken unawares, therefore, it is said he always carried a small bible in his coat pocket. He had also a great folio bible on his counting house desk, and would frequently be found reading it when people called on business;”
Finally, when the grim reaper approached Tom to take his life as payment for his pledge, he ran. With all the energy he could muster, Tom Walker attempted unsuccessfully to outrun death:
“Away went Tom Walker, dashing down the streets; his white cap bobbing up and down; his morning gown fluttering in the wind, and his steed striking fire out of the pavement at every bound. When the clerks turned to look for the black man he had disappeared.”