Had this been a more impersonal transgression — say, for treason or election fraud — it would be easier to understand who deserved the black fedora. The margins of the law would be the only thing that mattered. But this was a sexual transgression, and that complicates everything else. It taps into feelings that are impossible to separate from our own experience. Social activists are constantly trying to convince the world that personal actions can have political consequence, but this kind of gossip presented the opposite condition; this was a rare instance in which people instantaneously personalized a political drama that was detached from who they were or what they did. It caused them to think about the news in the way they traditionally thought about regular romantic life. It caused them to consider newsmakers as sexual beings. And as a result, feelings about who deserved to be hated in this circumstance were (at least partially) based on the worst possible criteria: what these people happened to look like, and how much they talked about it.

  Nothing twists and obscures day-to-day human existence as much as physical attraction. It pushes our minds in every direction simultaneously; it makes people more and less popular at the same time. Being attractive is like being famous — people will listen to you longer, convince themselves that what you’re saying is more interesting than it actually is, and laugh at jokes that aren’t funny. It’s also a justification for randomly hating someone, or for questioning the legitimacy of his or her merits and eroding whatever compassion that person might deserve (this is because beautiful people are never supposed to complain about anything). If you’re single, it’s important to be thin and well groomed (because this gives you a competitive romantic advantage); if you’re already in a committed relationship, it’s better to be a little overweight and casually disheveled (because this makes you less artificial to those who no longer view you as romantic competition). The way people look is so central to how we live (and how we respond to interpersonal conflict) that we’ve managed to collectively underrate its import. We all concede that appearances matter way more than they should, but we try not to dwell on this reality in practical conversation; somehow, it seems superficial to directly address how much beauty and ugliness inform consciousness. Instead we use less direct language to make the same soft points and draw the same soft conclusions. This complicates problems that are already complicated.

  Case in point: This is a book about villainy. I am writing about villains (or, in some cases, perceived villains). However, I’m not writing about serial killers. This is because serial killers don’t seem like villains; they seem subhuman. When examined with any degree of distance, they are depicted as either inarguably evil or criminally insane. There’s a density to their personality but not to their character; if you write about Ed Gein or Albert Fish, you’re mostly just cataloging the gruesomeness of their violence or the darkness of their damaged childhoods; there’s almost always a sexual component, but the sex is intertwined with the depravity of their sickness. However, there’s one glaring exception to this: Ted Bundy. Bundy killed and raped at least thirty women. His origin story and his psychological profile are similar to those who shared his appetites (to be fair, he was probably a little smarter than most serial killers, but only slightly — he managed to get into the University of Puget Sound law school, but his LSAT scores were average and he never finished his degree). Sometimes he would just break into coeds’ apartments and bludgeon them to death while they slept. He was a brutal killing machine. Yet this is not the image of Bundy that exists in the cultural imagination. This is not what people talk about when they reference Bundy as a metaphor. Bundy is best known for being the handsome serial killer. [When Joyce Carol Oates wrote about Bundy in 1994, she called him “eerily glorified.”] He is mostly remembered for one magnetic aspect of his criminal history: his ability to “seduce” women into following him into secluded areas so that he could murder them in private. His “seduction” technique essentially involved pretending he had a broken arm, asking random women for help with his stranded vehicle, and then hitting them in the head with a crowbar (there’s four hours of audio tape in which Bundy describes this process in cold detail, a series of confessions now used by the FBI for interview training). I suppose this is not so much seduction as it is straightforward lying. However, it clearly did work; his female victims did believe his lies. Now, we will never know how much of that success was directly due to his physical appearance. But it played a role.

  Bundy wasn’t Taylor Kitsch (or even Mark Harmon, who portrayed Bundy in the 1986 made-for-TV movie The Deliberate Stranger). But he didn’t look like a serial killer. I’m not sure what “looking like a serial killer” would even constitute, but I know it doesn’t mean a guy who resembles Ted Bundy. And this is something that Bundy himself realized. He knew that being relatively attractive gave him illogical advantages. In 1977, Bundy was being held in Garfield County Jail in Colorado, awaiting trial on a murder charge (he’d already been convicted on a kidnapping charge). He escaped. How did he escape? He jumped out of a second-story window in the courthouse law library, where he was allowed to prepare for his upcoming trial. He was allowed to study in the nonsecure library, all by himself, without handcuffs or leggings. Granted, no one realized (at the time) how dangerous Bundy was. But it still seems odd that a convicted kidnapper charged with murder would be placed in such an easily exploitable position. It was as if the local authorities looked at Ted and simply thought, This is not the kind of person who escapes from jail. Charisma goes a long way.

  Seemingly every serial murderer is also a sex offender. The relationship is almost one-to-one; the fact that Bundy focused on college girls and dabbled in necrophilia is not unique. What is different, however, is the way Bundy’s deviancy is normalized by the rest of society. This is a person who once tried to rip off a woman’s nipple with his teeth. He assaulted another woman with a medical speculum. His depravity was beyond the pale. Yet how was this behavior described by psychologists? According to Bundy biographer Ann Rule, the psychiatric conclusion was that Bundy had a “fear of being humiliated in his relationships with women.” This almost makes him seem like a normal, insecure dude. In the final hours before his 1989 execution, Bundy claimed his pathology was created by an addiction to pornography. This is almost certainly untrue; Bundy happened to be talking to an anti-porn advocate when he made this specific declaration, and he’d blamed many other entities in the past (including the victims themselves). But it was a savvy lie. It further galvanized the relationship between Bundy and mainstream sexuality. It made him seem less like a fiend and more like a deeply troubled person (which — in this case — is far more desirable). Sometimes people writing about Bundy will mention how it was ironic that, as a college student in Washington, he wrote a manual to help women protect themselves from rapists. This is, I suppose, one example of irony. But I don’t think people would use the word irony if a young Jeffrey Dahmer had written a handbook on how to avoid sexually confused cannibals. Dahmer wasn’t handsome enough. We’d use the words “predictably diabolical” instead.

  If this seems like an extreme, convoluted way of arguing that “attractive people are treated differently from normal people,” I apologize. I’m a weird-looking person, so perhaps I have an unconscious bias against the beautiful. But I don’t think that’s what’s happening here. In fact, I suspect my true bias mirrors the bias of almost everyone I’ve ever met: I view reality through the lens of someone predisposed toward treating attractive people differently than everyone else (and mostly to their benefit). If Kate Upton pulled a gun on me, I don’t think I’d beg for mercy. I think I’d try to make conversation. “You’re threatening to shoot me,” I’d remark. “That’s so empowering.”

  “It’s not the sex. It’s the lying.”

  I wonder how many times I heard this in 1998. It was the one-sentence way to express the conventional wisdom about the Clinton-Lewinsky scandal, and it seemed so reasonable. (Had Face-book existed in ’98, it would have
been the default status update for every boring person you know.) In just seven words, the sentiment made a clear argument: The fact that Clinton had an affair was not appropriate, but the fact that he lied about this affair was momentous and unacceptable. It was an intolerable decision. So this is what people said: “It’s not the sex. It’s the lying.” Which was totally idiotic and completely untrue.

  Presidents lie all the time. Really great presidents lie. Abraham Lincoln managed to end slavery in America partially by deception. (In an 1858 debate, he flatly insisted that he had no intention of abolishing slavery in states where it was already legal — he had to say this in order to slow the tide of secession.) Franklin Roosevelt lied about the U.S. position of neutrality until we entered World War II after the attack on Pearl Harbor. (Though the public and Congress believed his public pledge of impartiality, he was already working in secret with Winston Churchill and selling arms to France.) Ronald Reagan lied about Iran-Contra so much that it now seems like he was honestly confused. Politically, the practice of lying is essential. By the time the Lewinsky story broke, Clinton had already lied about many, many things. (He’d openly lied about his level of commitment to gay rights during the ’92 campaign.) The presidency is not a job for an honest man. It’s way too complex. If honesty drove the electoral process, Jimmy Carter would have served two terms and the 2008 presidential race would have been a dead heat between Ron Paul and Dennis Kucinich. Expressing outrage over a president’s lack of honesty is like getting upset over a sniper’s lack of empathy: It’s an integral component of the vocation. So when people said, “It’s not the sex. It’s the lying,” they were pretending — either to themselves or for the benefit of other people. They were trying to work through this as a problem that could exist in their own life, and they were trying to reconcile how they would manage the crisis. But this was not about lying. The president of the United States of America is obviously going to lie about cheating on his wife.

  It was about the sex.

  For the sake of clarity, here is a super-simplified overview of what technically transpired: It’s the 1990s. It’s a best-case scenario for an American president. After five decades of adversarial stasis, the United States is the lone international superpower, engaged in no meaningful wars (either hot or cold). The economy is booming and the nation is safe, so people are making up problems to be worried about: the looming Y2K disaster, northern spotted owls, the absurdity of Metallica headlining Lollapalooza. Clinton is neither popular nor unpopular; his first-term Gallup approval rating is 50 percent. In 1995, Lewinsky — an affluent twenty-two-year-old child of divorce with a degree in psychology — gets an unpaid internship in the White House. The president begins flirting with her, or she begins flirting with him (probably both). On November 15 of 1995 (eleven days before becoming a full-time employee), Lewinsky encounters the president in the office of the chief of staff and somehow ends up showing him the strap of her thong underwear. Clinton has never discussed this incident, but one assumes he must have thought, This seems promising. That same night, Clinton asks Lewinsky if he can kiss her. She agrees. The affair begins in earnest. They never have traditional intercourse, but Clinton spends a lot of time investigating the texture of her bosom and receives a boatload of fellatio, some of which occurs while he is on the telephone with a member of Congress. As one might imagine, this is an unconventional relationship. At first, Clinton does not let Lewinsky bring him to orgasm, claiming he needs to trust her more. Eventually his trust grows (and this will be his downfall). On March 31, Clinton inserts a cigar into Lewinsky’s vagina, returns the cigar to his mouth, and supposedly says, “It tastes good.” They exchange inexpensive, inappropriate gifts that reflect the gap in their maturity (he gives her things like Walt Whitman’s Leaves of Grass while she gives him a souvenir coffee mug featuring the words SANTA MONICA). Clinton tells Lewinsky they must keep their relationship ultraprivate; she promises to tell no one, but she is twenty-two years old, so “no one” means her therapist and her mom and a bunch of her friends over e-mail. Sensing (realizing?) the stupidity of his situation and realizing (fearing?) how it could affect his reelection, Clinton distances himself from Lewinsky. She is transferred to a job at the Pentagon on April 16. On May 24, Clinton explains that they can no longer have a sexual relationship; she tries to emotionally persuade him otherwise, but he rejects her pleas.

  Once the affair is over, things become more fragile and about a thousand times more political. A distraught Lewinsky begins confiding in one of her Pentagon coworkers, Linda Tripp. Tripp is roughly twice Lewinsky’s age and had previously worked for G. H. W. Bush. On the advice of a friend in the publishing industry, Tripp begins surreptitiously taping phone conversations with Lewinsky, probing her for details about the affair. This is where things get confusing. Tripp ends up delivering these tapes to Kenneth Starr, who wants them for a byzantine purpose: If Starr can prove that Clinton had an affair with Lewinsky, it will mean Clinton had lied under oath in a deposition involving Paula Jones, an Arkansas woman suing Clinton for sexual harassment that had allegedly occurred while he was still a governor in 1991. Now, what makes all this so twisted is that Starr’s original motive for investigating Clinton had nothing to do with anything sexual. Starr was looking into the Clinton family’s financial involvement in a corrupt 1970s land deal (the mostly forgotten “Whitewater controversy”) and the quasi-mysterious suicide of Vince Foster (who’d briefly worked as a White House counsel before shooting himself in 1993). So what we have, in essence, is a lawyer (Starr) failing to prove impropriety on one issue (Whitewater) and subsequently attempting to continue the pursuit of his target (Clinton) through totally different means (Lewinsky), based on an unrelated impropriety (Jones) that happened sometime in between. The linchpin is Tripp, who has both the incriminating audio cassettes and knowledge of a blue dress in Lewinsky’s closet that includes remnants of Clinton’s semen (like I said — he trusted her eventually). Tripp convinces Lewinsky not to dry-clean the dress, as this DNA could be exchanged for immunity (which Lewinsky needs, because she’d lied under oath in the Jones case, too).

  The story is broken by the Drudge Report, substantiated by the Washington Post, and then reported everywhere. Clinton is asked about the allegation and lies so directly (“I did not have sexual relations with that woman”) that it seems as if he must feel secure in his safety; even casual detractors who are certain of his guilt concede there must be no proof (because no tangibly guilty man would lie so brazenly). But the blue dress cannot be denied. Lewinsky turns the garment over to the prosecution in July; a month later, Clinton goes on TV and admits to the affair. It is the lowest point of his presidency. In December, he is impeached by the House of Representatives. It appears as though his sexual appetite has destroyed his career, just as his oldest enemies always predicted. Yet the impeachment has the opposite effect. It not only fails, but also dramatically improves Clinton’s perception and likability. During the week before Christmas, his approval rating hits 73 percent, the highest it will ever be.

  That December, Clinton’s unprecedented approval did not feel nearly as strange as it does in retrospect. At the time, the explanation for why he became so popular was framed as a compliment to the American people: It (supposedly) proved that the populace was more sophisticated than the media and the government. Lewinsky coverage was ubiquitous, and the potential consequences of impeachment were massive, but — given their sudden support for the man at the scandal’s center — it seemed as though normal citizens realized that this fiasco was not critical to the fabric of American politics. It was just gossip that turned out to be true. But that’s precisely why it matters.

  “Nobody roots for Goliath.” This is what Wilt Chamberlain used to say about himself (and he must have said it constantly, because I don’t think I’ve ever read a single overview of his career that didn’t repeat that quote verbatim). The reasons Chamberlain was vilified could be a book unto itself; he remains the gold st
andard for an athlete who was both unstoppable and unpopular. Normally, one would have expected the animosity toward Wilt to fade over time, and certainly in the wake of his 1999 death. We should all love him now, because dead men are loved. The things that exasperated Chamberlain’s critics — his obsession with numbers, his unabashed selfishness, the inability to elevate his game when it mattered most — should be secondary footnotes to his overall body of work (a statistical monolith that certifies him as the most dominant basketball player of his or any generation). But Wilt made one final mistake, eighteen years after his retirement: In 1991, he published a book titled A View from Above, in which he claimed to have had sex with twenty thousand women. By his own mathematical calculation, this would be an average of 1.2 women a day from the time he was fifteen until he was fifty.

  Now, this feat is obviously impossible. It was just an example of Wilt trying to be provocative. But people really hated this. They still remember it, even though the book itself is forgotten and out of print. And what’s crazy is that Wilt’s life did involve an insane amount of sex (not 1.2 women a day for thirty-five years, but more than any reasonable humanoid possibly requires). It was one of the central qualities of his personality; he was a lifelong bachelor and a serial womanizer. If the real number of his sexual conquests could somehow be tabulated, it would still astonish anyone who isn’t a porn star. The number “20,000” is not what people find distasteful. What people find distasteful is that the source of that number was Chamberlain. If Bill Russell had given an interview and said, “You know, I won more NBA championships than Wilt, but that guy slept with twenty thousand women,” Chamberlain’s approval rating would have soared (while Russell would be viewed as both magnanimous and jealous). We’d think of Wilt the way we think of Bob Marley, an introvert who sired eleven children with seven women (but is still adored). If Jerry West had claimed in his autobiography that “I was really embarrassed by Wilt as a teammate. This is a guy who slept with twenty thousand women,” people would view Chamberlain as compelling and complex (while West would seem self-righteous and lame). The number “twenty thousand” wouldn’t be any less implausible, but the impact would be totally different. It would change the way we think about Chamberlain as a basketball player, even though his sex life and his rebounding have no link whatsoever.