Deals with the devil
A bargain struck with a figure who takes something in return. Something is given and something is got, and the price is usually innocence, ownership or the soul. In Father Figure the deal is the record contract read as a Faustian one, and by the final chorus the speaker is the devil being dealt with. In Would've, Could've, Should've the bargain is struck at nineteen and cast as a dance, drawing on the folk tradition of the devil who appears at one to claim a soul, as in the legend of Rose Latulipe. The devil here is a counterparty, not a measure of how bad a thing is.
The bargain gives Taylor a way to write about a harm she had a hand in. Someone was on the other side of it and something was handed over, which turns a loss into a transaction and lets it be priced. A record contract can then be judged the way a soul is judged, and a girl of nineteen can be shown agreeing to terms she could not have understood.
Appears in 2 songs
“I damn sure never would've danced with the devil At nineteen”
Dancing with the devil represents the speaker taking a chance that imperiled her mortal soul, entering a relationship with an older man (John Mayer) that destroyed her innocence.
“I can make deals with the devil because my dick's bigger”
The deal with the devil represents the Faustian bargain of signing with a record label, the artist gains fame and wealth but surrenders control and ownership. The devil-dealing capacity is framed as a boast of the mentor's power.