Oliver Bacon, the protagonist of Virginia Woolf’s story, has an ambivalent attitude toward his past. He is amused when he remembers the enterprises in which he engaged to begin his path toward prosperity. Thinking about his younger self, a “wily astute boy” who sold stolen dogs, for example, he “chuckles.” He is keenly aware of the distance he has come from the “filthy little alley” where he grew up. This ambivalence is summed up in Woolf’s phrase, “he dismantled himself.” Oliver is proud, even arrogant, when he considers the distance he has traveled; he frequently pauses to admire his attributes and accessories, such as his “shapely” legs, pants, and boots. His constant harking back to the past borders on obsession.
Countering the pride is a suppressed shame, as he also remembers his mother’s reproachful tone when she commented on his illegal activities. He projects that disapproval onto his colleagues, imagining that he hears them “murmur” about him. Constantly looking back shapes his approach to the future as well, as he “snuffs” like a pig searching for truffles for a “bigger further off” prize.
Oliver has a somewhat ashamed view of his past. He is definitely unhappy with his checkered history and doesn’t want it to be brought to light, but he is certainly happy with where he has gotten, now a wealthy and industrious individual. He speaks to himself with pride at having “made it,” constantly referring to his life in an alley and how he has progressed to be fitted in all the trappings of wealth.
At the same time, he doesn’t want others to know about his history. He is ashamed of the squalor in which he once lived, because even though he is now wealthy, he wishes to be associated with everyone who was born and raised in wealth. So, his attitude overall is one of smug satisfaction yet hidden shame.
Oliver looks at his past with both satisfaction and disdain. He's proud of his meteoric rise but also ashamed of his beginnings; he's aware that he'll never be as highly regarded as he would be with a less questionable background.
At the beginning of the story, Virginia Woolf writes:
"Behold Oliver," he would say, addressing himself. "You who began life in a filthy little alley, you who…" and he would look down at his legs, so shapely in their perfect trousers; at his boots; at his spats. They were all shapely, shining; cut from the best cloth by the best scissors in Savile Row. But he dismantled himself often and became again a little boy in a dark alley.
He starts the statement by admiring himself for the trapping of his wealth and success—his fine clothes. However, he picks himself apart and mentally pushes back to being a little boy who didn't have many choices or much opportunity. Even though he's a different person and outgrew that place, he still can't quite escape it mentally. He yearns for a higher social class.
That's why at the end of the story, he makes a bad decision and trades lots of money for fake pearls. When the chance to spend time with the high-born girl he loves is dangled in front of him, he goes against the common sense that helped him rise up from the streets, gives the money to the Duchess, and soon finds out he was fooled.
Oliver Bacon has become a very successful businessman as a phenomenally wealthy jeweler. He has as much money as he can spend and leads a suitably lavish lifestyle. However, the one thing he lacks is high social status. He originally hails from a poor, humble background. Despite his vast riches, he's acutely aware of how the upper-classes still look down on him.
Oliver can't do anything to change his past, but he can still determine his own future. He sees the Duchess's predicament as a great opportunity to inveigle his way into the upper echelons of society. He knows full well that the Duchess is palming him off with fake diamonds, but he still plays along with the charade because the knows that he'll get something out of the arrangement that's more valuable to him than any precious jewel—the opportunity to marry into the old upper classes.
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