In Chapter 9, Tom White first appears in Osage County, ready to investigate the murders on behalf of the burgeoning FBI. Grann uses a simile to describe the disorganized files White receives from local law enforcement officers:
The files on the murders of the Osage contained history in its rawest form: bits of data vacuumed up without any chronology or narrative, like a novel whose pages were out of order.
By comparing the files to "a novel whose pages were out of order," Grann conveys a few ideas. First, it is clear to White that there is a plot to be found amidst all the disorganized notes. That is, corrupt and incompetent officers of the law have failed to put together even a basic story about the murders, even though they have plenty of material to do so. Whatever their motives, they have not done their job.
Second, the simile also draws a parallel between the role of the investigator and the role of the journalist. Grann is writing a nonfiction book that is structured much like a novel. Both he and White find themselves tasked with spinning "history in its rawest form" into a "chronology or narrative" that people can consume.
Finally, the simile draws the reader, too, into the investigation by likening White to the reader of a novel. Reading a novel is often a passive act, but it does not have to be. Even if it is not the reader's job to piece together the plot, characters, setting, and other elements into something cohesive, a good reader should be able to spot when this work has not been done. The law enforcement officers previously involved in the investigation did not do enough to turn "bits of data" into a true case, but White is a good enough "reader" to notice the disorganization and do something about it. Grann's simile invites the reader to actively notice the way Grann's book is put together and to think critically about the investigation. It is a reminder that Grann, too, started this whole process as a curious reader. That is what led him to notice that even White's investigation had some plot holes.
In Chapter 12, Grann describes the paranoia that began to mount among his investigative team as it became clear that someone was leaking information. He uses a simile to emphasize the danger in which they found themselves:
At night, White sometimes met with his team in the countryside, the men huddling in the dark like fugitives.
White and his team are supposed to be lawmen, tasked with hunting down "fugitives." Here, though, they find that they might be on the run just as much as the suspects they are pursuing. Indeed, Grann has just been describing Kelsie Morrison's insistence that White find who is committing the murders before they kill him for informing on them. Morrison himself turns out to be one of the killers, demonstrating that anyone can be working both for White's team and for the criminal underbelly they are investigating. The boundary between law and crime is permeable.
The use of the term "fugitive" is notable in the context of United States history. For a long time, the idea of "fugitivity" was especially linked to enslaved Black people on the run from their enslavers. The history of the term itself complicates the idea that there are such things as "good guys" who follow the law and "bad guys" who break the law. Enslavers could behave in morally reprehensible ways without ever breaking the law, and enslaved people could be called lawbreakers simply for trying to escape horrendous abuse. Grann is not equating White and his team to enslaved people on the run, but he does appear to lean on the term's complex history to suggest that law enforcement and crime are not easily distinguished categories in Oklahoma during White's tenure with the FBI.
In Chapter 16, Grann uses a metaphor and a simile to describe how Hoover reinvents the FBI:
Under Hoover, agents were now seen as interchangeable cogs, like employees in a large corporation. This was a major departure from traditional policing, where lawmen were typically products of their own communities. The change helped insulate agents from local corruption and created a truly national force, yet it also ignored regional difference and had the dehumanizing effect of constantly uprooting employees.
Grann first describes the way Hoover began to see agents as metaphorical "cogs" that could be easily changed out, one for another. He then uses a simile to clarify that for Hoover, this metaphor was coming less from an admiration of machinery than of corporations. Corporations and proponents of capitalism have long used machinery as a metaphor for how employees can work together to efficiently accomplish business goals. The metaphor helps illustrate how the division of labor helps jobs get done faster than they would if one person were to work on every step in the process. By the time Hoover was installed as head of the Bureau of Investigation, mechanical language was entrenched in the way people talked about business. Especially given that some of the most successful businesses at the time were car manufacturers, it makes sense that Hoover talked about workers in this way.
More telling is the fact that Hoover thought of these human cogs as "interchangeable" and that he wanted the agency to function like a large corporation at all. Prior to Hoover, law enforcement did not function as much like a business with profit margins and a single bottom line across the country. Money was certainly part of local law enforcement, with officers taking bribes often enough. However, Hoover sought to consolidate all local law enforcement as a "national force" with a single interest. This idea of a consolidated police force was new, and Hoover borrowed it from the blueprint of corporations like the Ford Motor Company. Just like Ford, Hoover's agency would use an assembly line of workers to enforce Hoover's idea of order across the United States. This new way of doing things was controversial because the United States is a diverse place. People like Tom White weren't sure that it could account for the nuanced reality of different people and places around the country. Still, Hoover more or less got his way. He turned the Bureau of Investigation into the Federal Bureau of Investigation, which to this day functions as a massive agency enforcing federal laws all over the country.
In Chapter 23, Grann pores over archival material that helps him see facts about the Osage murders that people like Mollie Burkhart could not see when they were alive. He uses personification and a simile to express a sense of uneasiness over his relationship to history:
History is a merciless judge. It lays bare our tragic blunders and foolish missteps and exposes our most intimate secrets, wielding the power of hindsight like an arrogant detective who seems to know the end of the mystery from the outset.
Grann personifies history as a "merciless judge." A judge metes out decisions and punishments after carefully reviewing all the facts of a case. They have the luxury of looking at these facts from a place of calm, rational detachment. Anyone who appears before a judge likely did not have that same luxury while living out the facts of the case. "Tragic blunders," "foolish missteps" and "intimate secrets" often appear obvious in the historical record, but we usually do not have a historical perspective as we are living our lives. Grann realizes that piecing together the history of the Osage killings involves "laying bare" the human failings of Mollie and other targets of the murders. He wants to honor the Osage by telling this story, but it also feels like a "merciless" act.
Grann shifts from personification into simile, comparing history now to "an arrogant detective who seems to know the end of the mystery from the outset." This comparison helps Grann further explore the goals of his own project. As a detective in his own right, Grann imagines that he is not exactly making history, but rather competing with history to solve the murders. This is difficult and frustrating work because history has secrets that have not made it into the archive Grann is using to solve the case. History will inevitably win, but Grann might guess a few things correctly before they are revealed at the end. He strives to be a kind human counterpart to merciless history, helping people understand the past a little better while they are still alive.
At the same time, there is a lingering sense that Grann hopes his work will make it into the historical record. In fact, it has: his book has brought new attention to the Osage Reign of Terror and has since inspired an Oscar-winning film.