Following his agreement with Old Scratch, Tom becomes a usurer, a person who lent money for interest. The attitude of Irving toward such people (Irving was writing at a time when the commercial economy was expanding by leaps and bounds) is summed up by his quip that the devil was "anxious for the increase of usurers, looking upon them as his peculiar people." Tom agrees to the devil's proposal, having balked at his request that he become a slavetrader, and works at a Boston counting house.
Irving tells his readers that this (the 1720s) was a time when a loose paper money policy by the Massachusetts government had led to a speculating frenzy. The "speculating fever" this created led to a major crash, and the people of the colony were experiencing hard times. Tom received people desperate for cash, squeezing them for every penny he could get on terms that were even more extortionate than those Old Scratch had recommended:
He accumulated bonds and mortgages; gradually squeezed his customers closer and closer: and sent them at length, dry as a sponge, from his door.
In this way, Tom becomes very wealthy at a time when many Bostonians were struggling. Eventually, he begins to fear for his soul, and becomes a very pious churchgoing man. But it is too late, as fittingly, Old Scratch comes to collect on his debt (Tom's soul) in the same way Tom had squeezed his customers for their money.