In the following passage from Chapter 1, Du Bois complains that Black people have not yet found their freedom in the years since the American Civil War. He utilizes simile to outline the Black journey for the reader:
The first decade was merely a prolongation of the vain search for freedom, the boon that seemed ever barely to elude [Black Americans'] grasp — like a tantalizing will-o'-the-wisp, maddening and misleading the headless host.
In this passage, Du Bois compares freedom to a will-o'-the-wisp, which is a mythical creature known for appearing to lost travelers in the woods and luring them deeper in, eventually to their death. This particular simile emphasizes the virtual hopelessness felt by Black Americans striving for equality and freedom: as the promise lures them deeper and deeper, they remain hopeless, wandering meandering and headless in woods until their death.
This simile highlights the false promise fed to Black Americans by Emancipation: namely, that they would quickly, over the course of time, find themselves on equal footing with their white brethren and share in the benefits of American citizenry. This, of course, ended up being a false promise—one which Black Americans continued to chase even after being denied it for decades thereafter.
In Chapter 1, Du Bois highlights the fact that many Black men wish to become, in his words, "co-worker[s] in the kingdom of culture." He notes that this ability to resoundingly impact society has not, in the past, been absent or withheld from Black men; but rather, their work has been obscured. This he details through simile:
The shadow of a mighty Negro past flits through the tale of Ethiopia the Shadowy and of Egypt the Sphinx. Throughout history, the powers of single black men flash here and there like falling stars, and die sometimes before the world has rightly gauged their brightness.
Du Bois uses simile to compare the abilities of exceptional Black men to falling stars, burning brightly and not having their brilliance recognized. Tragically, they disappear too soon, not remaining long enough to make a mark on the history books. Du Bois also implies here that the important works of Black men may have been expunged from the historical record or deliberately excluded—particularly if those works were ones of liberation, in opposition to the project of empire. It is a lonely thing indeed, to be excluded not only from one's own culture but from history; and Du Bois takes great pains to express the devastation that accompanies such exclusion.
At the end of Chapter 2, Du Bois chronicles the "death" of the Freedmen's Bureau, and with it the aspirations of recently liberated Black Americans. He states that in his own day and age, the specter of the work this bureau "did not do because it could not" remains; and the present "color-line" is the result of this inadequacy. Du Bois outlines the color line with characteristic imagery and simile:
I have seen a land right merry with the sun, where children sing, and rolling hills lie like passioned women wanton with harvest. And there in the King's Highway sat and sits a figure veiled and bowed, by which the traveler's footsteps hasten as they go. On the tainted air broods fear.
In this passage, Du Bois describes the so-called Promised Land, utilizing imagery to connect his description to that of the Bible, making such connections as the "King's Highway" for the more religiously-oriented reader. He uses simile to compare the rolling hills of the Promised Land to the bosom of a woman, "ripe" for harvest. Despite this imagery and figurative language, the Promised Land is not an unblemished place: the specter of racism and the color line sits blocking the path. Those who can ignore it choose to—but, Du Bois says, they can do so no longer.
At the beginning of Chapter 2, Du Bois describes the Union army's advance into the Southern states, and the resulting trail of Black refugees that would follow in the soldiers' train. Notably, Du Bois contextualizes the movement of fugitive slaves through the use of simile:
No sooner had the armies, East and West, penetrated Virginia and Tennessee than fugitive slaves appeared within their lines. They came at night, when the flickering campfires shone like vast unsteady stars along the black horizon: old men and thin, with grey and tufted hair; women, with frightened eyes, dragging whimpering hungry children; men and girls, stalwart and gaunt.
Du Bois uses simile in the above passage to compare the campfires of Union soldiers to stars—a comparison that is particularly apt, given the fact that enslaved people used the northern star to guide them on their journey to freedom along the Underground Railroad (before and during the American Civil War). This simile helps illustrate to the reader the exact light in which enslaved people in the South viewed the advancing Union army. These Union soldiers appeared as their ticket to freedom, a means of liberating them from the oppressive confines of plantation life and the horrors of chattel slavery.
Toward the beginning of Chapter 3, Du Bois includes a quotation from Booker T. Washington, whose general approach towards racism and reconstruction he disagrees with. In the following excerpt from the "Atlanta Compromise," Washington utilizes simile to outline the concept of "separate but equal" that would become the cornerstone of U.S. segregation policy:
In all things purely social we can be as separate as the five fingers, and yet one as the hand in all things essential to mutual progress.
In this complex simile Washington crafts to explain his proposal of "separate but equal," the fingers of the hand represent different racialized groups in America: in this instance, specifically Black and white people. Washington argues that, just like the fingers of a hand, Black and white people can remain isolated—culturally, educationally, even physically—but remain united by the "hand" of "mutual progress."
Du Bois disagrees strongly with this stance, arguing that separation in all things does not constitute equality or freedom for Black Americans. While Washington's strategy was successful in securing the sympathy of white southerners, its effectiveness deteriorates in the long run, Du Bois argues, leading only to further violence and subjecting Black southerners to abject poverty and second-class citizenship.
Du Bois begins Chapter 5 with a reflection on the city of Atlanta, Georgia—a center for both education and industry, from which Black Americans are excluded. Du Bois describes Atlanta's "awakening" at the dawn of the Civil War, personifying the city as a woman:
Once, they say, even Atlanta slept dull and drowsy at the foot-hills of the Alleghenies, until the iron baptism of war awakened her with its sullen waters, aroused and maddened her, and left her listening to the sea. And the sea cried to the hills and the hills answered the sea, till the city rose like a widow and cast away her weeds, and toiled for her daily bread; toiled steadily, toiled cunningly.
In the above passage, Du Bois begins by personifying the city of Atlanta, according her human pronouns and qualities such as the ability to sleep. This referral to an entire city as one "woman" allows Du Bois the liberty of generalizing its populace. Though they may not act as a collective, this particular use of figurative language imagines them as one. Furthermore, situated within this personification of Atlanta is a significant simile: her act of rising "like a widow" to "cast away her weeds," signifying her growth after the war into an industrial center.