“While nothing is easier than to denounce the evildoer, nothing is more difficult than to understand him”—so goes a famous aphorism often attributed to Dostoyevsky. The figure of the evildoer seems to cry out for either condemnation or interpretation. We can’t just let an evildoer be; we can’t just turn our eyes away from him until we’ve managed to satisfy ourselves that he is different from us. Murderers, having indulged in the greatest evil, exercise this magnetism to the greatest degree.

Enough has been written in the past few years about the true-crime genre, and certainly enough true-crime stories have been written, that almost everyone has formed an opinion about the merits and flaws of the genre. The tacit purpose of every new serial-killer documentary and murder-mystery podcast can’t be to denounce the evildoers behind the crimes, so it must be to understand them, hard as that may be.

In her new book, Scoundrel: How a Convicted Murderer Persuaded the Women Who Loved Him, the Conservative Establishment, and the Courts to Set Him Free, the journalist Sarah Weinman seeks to exhume a little-known killer from the dustbin of history, examining not so much the nature of his crimes as the way he was received by the society in which he committed them. She tells the story of how Edgar Smith, sentenced to die for murdering a young girl, charmed his way into literary stardom and eventual freedom by preying on the naïveté of the public. Weinman doesn’t want to figure out why Smith killed the girl, but rather why his actions were the object of a prurient and sympathetic fascination.

Weinman introduces Smith as an outlier presence in the otherwise tranquil suburbs of New Jersey, a handsome but unstable guy who couldn’t hold down a job and was always asking friends for car rides or loans. He had a wife and child but didn’t seem very devoted to them, and he was prone to isolated outbursts of anger. On the night of March 4, 1957, for reasons that are still unclear, Smith picked up a 15-year-old girl named Victoria Zielenski whom he knew from around town, drove her to a local sand pit, and beat her to death with two large rocks. Her father found her the next day in a “jackknifed position,” her clothes scattered around the area, her face so smashed and deformed that her father almost couldn’t recognize her.

It took only a few days for the police to zero in on Smith, who admitted to picking Zielenski up and who had discarded a pair of pants stained with her blood. The murder trial was a sensational event in the county (it provided a first inspiration for the crime writer Mary Higgins Clark), in part because of the horror of the murder and in part because Smith adopted a convoluted defense strategy, pinning the blame on a friend of his who had a firm alibi and giving several contradictory accounts of what happened on the night of the murder. The jury deliberated for less than two hours before sentencing him to death.

While Smith languished in the “death house” waiting for his end, his case attracted the attention of the prominent conservative commentator William F. Buckley Jr., who read about Smith in a local news article that documented his time in prison. The article mentioned that Smith was a fan of Barry Goldwater and of Buckley’s National Review, so Buckley decided to write him a letter. He soon found himself impressed by Smith’s intelligence and became convinced of his innocence, so much so that he wrote a long article in Esquire attacking the prosecution’s “inherently implausible” case. Buckley was in favor of stricter criminal justice more broadly and even of the death penalty, but in this case he believed the courts had erred. It’s unclear to what extent Buckley’s attachment to Smith had an ideological dimension; one of his colleagues at National Review speculated that “we were taken in…by our unwillingness to believe that anyone who loved NR could be a savage killer,” but Weinman also writes that it was Buckley “the person,” not “the ideologue,” who was “most directly affected” by Smith. In either case, their friendship was always tinged with a note of paternalism on Buckley’s side, as when he said that Smith’s voice “betrayed a background of football lockers and poolrooms”—a condescending blindness Smith knew exactly how to exploit.

Smith’s acquaintance with Buckley soon led to a much more intimate friendship with Sophie Wilkins, an editor at Knopf who coached him through the process of writing and publishing a memoir. The written correspondence between the two soon grew steamy (“I wanna mess around in all your orifices!!!”), but their infrequent in-person visits were always stilted, and at certain points Wilkins claimed she was only flirting with Smith to boost his confidence and get a book out of him. That memoir, Brief Against Death, debuted in 1968 to rave reviews, and the uncritical book review industrial complex soon allowed Smith to launder his reputation, making himself out (with Buckley’s assistance) to be a kind of gentleman intellectual who had been victimized by the justice system.

Thanks to generous legal contributions from Buckley and others, Smith also fought a decade-long war of motions and appeals, seeking to have his initial conviction overturned on the grounds that his confession had been coerced. (These days it’s normal for death row inmates to languish in prison for years before their execution, but at the time a case like Smith’s was unique.) The standards for criminal prosecution and the standing Supreme Court precedents on criminal justice were in flux (the Miranda case was decided while he was on death row), which gave Smith an opening to press his case. The media attention around the book may have helped his appeals garner momentum, but when a judge eventually did overturn his conviction, it was because of a legitimate flaw in the initial prosecution: Smith’s confession had been obtained under duress. Afterward, Smith accepted a plea deal: He admitted to killing Zielenski and got his freedom in return.

Given that Smith had written an entire book arguing his innocence and continued to portray himself as innocent even after taking the deal, most reporters and readers in the outside world did not take this admission seriously, instead viewing it as an attempt to exploit a legal loophole. Upon getting out of jail, Smith enjoyed a brief flirtation with celebrity, appearing on talk shows and giving interviews to journalists who followed him around for his first day of freedom. Before long, though, his old constitution took over—his next few books were worthless; he still couldn’t hold down a job; and his only talent seemed to be for roping in new women. A few years after his release, he decamped with one of them to San Diego, where he soon fell into penury. In October of 1976, he drove up to a woman on the street, pulled her into his car at knifepoint, stabbed her twice when she tried to escape, and then fled, spending a week on the lam before Buckley ratted him out.

Smith occupied an interesting middle ground between the common criminal and the Manson-esque serial killer. To what extent did he have a criminal character and to what extent a murderous one? His first crime was one of senseless sadism, but his second seems to have had an economic dimension—his first demand of the victim was that she give up all her money. For Weinman, his proclivity to violence against women was not the product of any childhood trauma or ideological vendetta; it was just there, seemingly beyond rehabilitation, latent for a while but always destined to return to the surface.

Weinman is reluctant to try to explain why Smith committed the crimes he did. Instead, she lets him speak for himself, quoting extensively from his correspondence to show how he flattered the prejudices of those around him. This builds a dramatic irony more tasteful than the kind one often expects in this kind of story, though even so it’s never quite clear to what extent Smith was deluding himself as well as his confreres, or to what extent he even thought of himself as a criminal. His self-analysis is of no help, since he only sometimes admitted that he killed Zielenski and often explained his actions with useless statements such as “I was angry.” At times he seems like a self-absorbed con man, such as when he hits up friends and family for rides and loans, but at other times, such as when he frightens a female National Review researcher by coming up to her unnoticed in the magazine’s offices, he seems like a genuine psychopath. It’s judicious of Weinman not to foist one interpretation or the other on her readers.

Weinman is also sparing when she discusses the Smith case in the larger context of criminal justice, though she does describe it as “a wrongful conviction in reverse,” one that “complicates the larger narrative of incarcerated people who proclaim their innocence.” She of course doesn’t mean for the story of Smith’s recidivism to serve as a counterpoint to the numberless false convictions that have been discovered and overturned in recent years, many of them the product of unethical prosecution, falsified evidence, or racist jury selection. Indeed, as Buckley himself reflected, Smith’s story really was the story of a wrongful conviction, since a high court ruled that the initial prosecution for the Zielenski murder violated his habeas corpus rights. In some sense, then, his release showed the system functioning as intended. It just so happens that in this case the guy whose rights the system was protecting was not only guilty but unrepentant and unreformed.

The loose connections between Smith’s story and the larger questions of criminality and criminal justice make Scoundrel a curious book, more a portrait of historical oddity than anything else. Years after she and Smith stopped speaking, Wilkins reflected to Buckley that “there is certainly a book in the weird coming together of three people as different as us, for a psychologist at least,” and indeed the story is weird enough to sustain a reader’s interest even in the absence of any broader takeaways about the criminal justice system. The attraction of this story comes from a truth that Weinman hints at but doesn’t say outright: No matter what they may have told themselves, Wilkins and Buckley were drawn to Smith not in spite of but because of the fact that he was convicted of a heinous crime. The fervor with which they argued for his innocence belies the almost quivering subtext of their correspondence with him. Even from the very beginning, they seemed to know that something was wrong with the man they had chosen to champion. Contra the maybe-Dostoyevsky quote, denouncing an evildoer may not be the easiest thing after all. The easiest thing may be to stare too long into the abyss and wait for it to stare back at us. To ogle evil, to examine its every detail, reassures us that we are outside it, divided from it. In truth, though, the boundary may be more tenuous than we want to believe.