As the black Cadillac carries the Boss out of Mason City in Chapter 1, Jack has a flashback to 1922, when he first met Willie. The scene takes place in Slade's, an illegal bar in Mason City that was often the site of political dealings. Jack, already in the bar's dark back room, sees Willie come in and already knows that their futures will intertwine:
Fate comes walking through the door, and it is five feet eleven inches tall and heavyish in the chest and shortish in the leg and is wearing a seven-fifty seersucker suit which is too long in the pants so the cuffs crumple down over the high black shoes, which could do with a polishing, and a stiff high collar like a Sunday-school superintendent [...]. It just comes in like that, and how are you to know?
Jack depicts Willie as "fate." This is, on its face, an instance of personification, as Jack depicts fate, the abstract concept, as a nearly six-foot-tall man in a seersucker suit. But the reader knows, in the context of the chapter, that Jack is referring to Willie. This presents Willie as fate, which makes it a metaphor: when Jack sees Willie enter the room, it is as if he sees his own future enter too. Jack understands, even at this first meeting, that Willie was an ambitious and powerful man, already possessing the qualities that would drive him to success in the future: "Metaphysically he was the Boss, but how was I to know?"
This passage also gives the most thorough description of Willie to this point in the book. Jack describes Willie's physical appearance and his clothes: Willie's suit doesn't fit and looks cheap. Jack says it cost only $7.50, about $140 in 2024 dollars, extremely inexpensive in a time before widespread mass-produced formal wear. But, with the clarity of hindsight, Jack understood that even this less glamorous version of Willie was still destined to be the boss. This is quite unusual for Jack. Normally, Jack doesn't believe in things like fate. But Jack's devotion to Willie, writing after his death, supersedes his atheistic worldview.