The retired Mr. Woodifield represents the foil to the boss’s busy but empty life. Although Woodifield is the one depicted as being in poor health, it is an ironic contrast to the boss’s emotional wounds. Woodifield does not see the boss’s despair, nor does he see the boss’s focus on materialism and work to be pointless, but instead sees him as successful despite his loss. Mr. Woodifield serves as a contrasting reminder that life goes on regardless of personal tragedies. Woodifield is still excited by the pleasures of his life, such as the stories of his children abroad and the whiskey given to him, despite the consequences of aging. In contrast with the boss, Mr. Woodifield is treated like a child as his old age renders him more reliant on others. He relies on his wife and children due to failing health, who only let him go out occasionally, and who limit his alcohol consumption. 

The boss is a benevolent figure to him, sharing whiskey, but only out of a sense of pity for Woodifield’s ailing memory. In return, Mr. Woodifield admires how the boss is older than him and yet maintains his freedom and is at the helm of his business. This sense of childish naivety is further reinforced by Mr. Woodifield’s casual discussion of a deeply painful subject to the boss, oblivious to the harm he causes. The irony of this dynamic is revealed at at the end of the narrative when the boss shares the same lapse in memory that earlier elicited his pity for Mr. Woodifield.