As soon as Tom arrives home that day, his wife tells him about the death of Absalom Crowninshield, and Tom remembers seeing his name hewn into the tree. Tom is reluctant to share the secret of his bargain with his wife but eventually he does; because of her extreme greediness, she urges him to take the deal. Determined to be contrary as always, though, Tom refuses just to get a rise out of her.
Finally she decides to go and take the deal herself. She is absent for many hours one day, but returns home with no luck; apparently Old Scratch was sullen and would not agree to her terms. He told her to go again with an offering, so she leaves for the swamp again with all of the valuables in their house tied up in her apron.
She never returned that day. Legend says many different things about what happened to her, but the most probable story is that Tom set out to find out what happened to his wife—and to reclaim the valuables she'd taken. Instead of his wife, he found her apron hanging in the branches of a tree near the Indian fort, with only a heart and liver tied up in it. According to tufts of hair and footprints at the scene, it seems she'd at least put up a fight against Old Scratch. Tom is more upset about the loss of property; in reality, he thinks Old Scratch has done him a favor by getting rid of his irritating wife.
Eventually Tom is impatient, and he decides he will agree to anything so long as he receives the treasure. He goes to find Old Scratch and they haggle about business; Old Scratch insists that money found through his means should be employed in his service. First he wants Tom to build a slave ship, but Tom refuses to be a slave trader; his conscience could not handle it.
Tom proposes instead that he become a usurer and extort bonds and foreclose properties by lending money with far too high an interest rate. Old Scratch agrees to this, and Tom sets up right away as a usurer in Boston.
The news of Absalom Crowninshield's death serves as a warning to Tom that dealings with Old Scratch often go astray, and that he'd be better off not getting involved. There are numerous warning signs like this along Tom's road to damnation, and each one he ignores is a bit further that he falls on his descent to hell through his loss of morals.
The loss of his wife is another one of these warning signs. Her disappearance serves as a test for Tom, which he fails with flying colors. He's more concerned with the loss of his property (the valuables she took to trade to Old Scratch) than with the loss of his wife—regardless of their poor relationship, it displays Tom's lack of human empathy overall, which ultimately leads to his downfall. Even after he sees that she's been killed, he chooses to go through with the bargain. Tom is more concerned with material wealth than with any person, even the one to whom he is married.
The final traces of Tom's morality make an appearance in his outright refusal to become a slave trader. It is ironic in light of his lack of conscience in all other respects, but it serves as a reference point; further on in the story when he deteriorates even more, readers can look back at the man who refused to be a slave trader because of his conscience and realize that after this moment, he passed the point of no return.
Tom's greed is further emphasized through his decision to use the wealth he gains through access to the treasure to acquire even more wealth, through extortion, manipulation, and hurtful money-loaning practices. He cannot ever be satisfied, and this greedy appetite is exactly what the story condemns. Greed that leads to more greed is the worst kind, and Tom Walker is on a slippery slope to hell because of it.
In this story, Old Scratch symbolizes temptation, as the devil typically does in stories. The Judeo-Christian creation myth is the earliest example of this, when the devil, disguised as a snake, tempts Eve to eat the forbidden fruit in the Garden of Eden, which causes her fall from paradise. Old Scratch is temptation, like the snake, and Tom is naiveté and greed, like Eve—though Eve was not greedy for material wealth, like Tom is, she coveted that which she could not have. The treasure is to Tom as the apple was to Eve, and in this section of "The Devil and Tom Walker," Tom kick-starts his own fall from paradise.