If you ask Elliott Jaffa about his background, you are almost certain to be impressed. He’ll tell you he has been a professional baseball player, a tiger trainer for the circus, a medical consultant on ER, and a writer for one of the most famous TV shows of all time, Seinfeld.

And if you actually believe he’s had all these jobs in his life, then you have joined the long list of people to be fooled by Jaffa.

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As Jaffa tells Urbo, “One of the best compliments I ever got was, ‘You love screwing with people.’” Jaffa—a behavioral psychologist (for real)—is someone who loves to lie to folks he meets about what he does. He swears he never deceives to do anything illegal or harmful, merely to have a bit of fun and test the limits of others’ gullibility.

In the long history of incredible impersonations, Jaffa is unquestionably a small-time offender. Where Jaffa has decided to pull back, others have unflinchingly marched forward down a long and complex path of untruths. These con men and women have bluffed their way into unbelievable levels of access. Urbo spoke to Jaffa and a few experts on lying to learn more about unbelievable deceptions people almost got away with.

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How did they do it? Why did they do it? And what can you do to find out the truth about a suspected imposter?

The Man Who Fooled NASA

NASA is pretty well-regarded as the workplace of some of the smartest people in America, if not the world, so pulling a fast one on the space agency is no small feat. But that is exactly what airline pilot Jerry Whittredge did in 1997.

Calling and pretending to be an ex-CIA officer who had been selected for a future NASA mission, Whittredge was able to arrange a tour for himself at NASA’s Marshall Space Center in Huntsville, Alabama.

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On the tour, Whittredge was invited into the high-security Mission Control room during a shuttle mission. On later dates, Whittredge—again, a pilot with no ties whatsoever to NASA or the CIA—was able to get top-secret information about NASA’s shuttle propulsion system, and even got to train in a NASA flight simulator at the Naval Air Station in Kingsville, Texas.

Eventually, Whittredge was found out and arrested by the FBI.

Jaffa, who tells tales of sneaking backstage at concerts in his youth, looks to his past for examples of just how important the right attitude is in these situations. “If you act like you know what you’re doing and you say it with a straight face and some authority,” he slyly reveals, “things work out.”

Another expert in gaining people’s confidence is Steven Keyl. A 20-year veteran of the intelligence community, Keyl offers companies social engineering consulting. He is the author of the book The Human Whisperer, a playbook for understanding and manipulating human behavior. Much of Keyl’s consulting work is built off his ability to gain someone else’s trust; his job is to “hack the people” at a company to test its employees’ ability to detect fraud.

Charm is key, according to Keyl: “Getting people to believe you is about being believable. It’s about being open and friendly and warm.” He says this kind of deception is something you can practice and learn.

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“[Being a convincing liar is] easy once you’ve done it a few times,” he says.

It would seem that this kind of trickery is an old-timers’ game, but there are plenty of examples of youths who can be total pros when it comes to deceiving others.

“A” in Confidence: Student Gives Lecture Posing as a State Senator

Sometimes it can be difficult to get high school students to care about politics, but in one case in Upper Sandusky, Ohio, a student got a little too involved.

Izaha Akins, an 18-year-old at Mohawk High School, posed as a newly-appointed state senator and gave a speech to an American Government class. Akins received a tour of the school and even enjoyed a chauffeured ride to and from the school courtesy of a local car dealership. Akins, though, is decidedly not a state senator.

The politician scheduled to give a speech was Ohio Senator David Burke. But weeks before Burke’s visit, Akins called the school to tell them Burke had resigned and that he had been appointed in Burke’s place. The visit was rescheduled for an earlier date, which is when Akins made his visit.

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No one noticed the hoax until Senator Burke showed up on the day he was scheduled to speak. Akins was arrested.

He claimed he had perpetrated the fraud to prove a point about school security, arguing that a simple Google search would have revealed his fraud. Luckily—or perhaps unluckily—for Akins, the story he had concocted was intricate enough that no one from the school thought to check.

To that point, Jaffa explains that little details can go a long way in certain lies. For example, Jaffa shares that he dislikes giving up his car for valet parking. He tells the story of the time he parked his car in front of an event and handed off his keys to the attendant, only to circle back and pull the attendant aside. “I talk to the attendant, and I tell him ‘I’m afraid I can’t authorize you to drive my vehicle because there are two loaded weapons inside.’” The valet attendant quickly handed Jaffa the keys back, allowing the car to stay parked in front.

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Jaffa says his use of specific words like “authorize” and “vehicle” gave him an air of authority—“It sounds official.”

Experts like Keyl affirm that building a case of believability is critical when trying to convince someone of something that is not true.

The 33-Year-Old High School Cheerleader

Frauds can go far beyond a couple of clever lines to an unwary valet worker. Take the fascinating case of Wendy Brown, a 33-year-old mother who successfully started taking classes at a Wisconsin high school and even made the cheerleading squad, all under the guise of her teenage daughter (who was enrolled in school in a different state).

They really are that person in their minds. Almost like method acting, someone gets so deep in a character that they become that character.

According to Brown, she had a terrible time at high school and never had an opportunity to join the cheerleading squad, giving her the impetus for a radical re-enrollment. Brown had a difficult upbringing and troubled past, so though she had previously perpetrated frauds and minor thefts, she was sentenced to three years in a mental facility rather than jail time.

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Jeff Maysh (via The Atlantic)

For insight into such drastic deceptions, Urbo spoke with Dave Popple, PhD, a corporate psychologist who consults with major companies and has a knack for finding people with something to hide. He supposes some of these cases might include a high level of self-deception, making it easier for the perpetrators to deceive others.

“People actually believe these exaggerated behaviors and lies,” says Popple, “When they present themselves this way, people trust them.” From his work in the corporate sphere, Popple observes that as many as one in twenty people perpetrate a significant level of self-deception. “In their minds, all this stuff is true.”

What makes someone a good liar?

What makes the case of Wendy Brown so interesting is that keeping up her lie was essentially a full-time job. Reports reveal that Brown changed her behavior when acting as a high school student—giving a genuine performance as a slang-talking teen.

Dan Ribacoff, another expert in deception, is CEO of a private investigation firm and a lie detection specialist. He says the same principles guiding frauds like Brown’s are found in the work of performers for the stage and screen.

“An actor is a good liar,” Ribacoff shares. “They are practiced liars!”

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Brown fitting in at a high school or Whittredge infiltrating NASA illustrates how people become a different character and believe it. Such commitment to these fraudulent identities is effective, says Popple, and makes them even harder to detect.

“There is not a hitch to their behavior,” he says.

According to Popple, these extraordinary impersonations are not unlike the most extreme examples of intense method actors like Daniel Day-Lewis: “They really are that person in their minds. Almost like method acting, someone gets so deep in a character that they become that character.”

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Popple says people in these situations take advantage of the fact that their lies are so improbable that they are rarely met with high scrutiny. “The small lies are easier to catch,” he explains.

So someone lying about their GPA will probably get found out, he says, while someone lying about going to Harvard might actually get away with it, because who would make such an egregious lie?

In a similar vein, Popple recalls how Winona Ryder was able to get away with so much shoplifting because, as a well-known celebrity, it was so unlikely that she would try to steal from designer stores.

The Dark Side of Lies: A Fake Doctor Gets a Real Prison Sentence

Few other stories can compare to that of Gerald Barnes, a chief physician at a Los Angeles health clinic who was described by colleagues as affable, professional, and generous. He also turned out to be a complete fraud who had never stepped foot inside med school.

Barnes’ given name was Gerald Barnbaum (though he changed it to Barnes), and, starting in 1976, he spent much of his life impersonating medical professionals and landing himself in prison. It is perhaps not surprising that Barnes was known as a talented actor in his youth.

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California Department of Corrections and Rehabilitation (via CNBC)

Barnes’ impersonation led to tragedy when, in 1979, he misdiagnosed a patient who had complained of dry mouth, dizziness, and other symptoms. The man needed emergency care for uncontrolled diabetes, but Barnes sent him home. The man passed away from the condition two days later. Even after serving jail time, Barnes continued to find his way back into work as a medical professional.

Bizarre cases like Wendy Brown entering high school or Gerald Barnes pretending to be a doctor raise the question as to why some take these frauds to such detrimental lengths.

Keyl explains that such individuals are likely psychopaths, though that term is often misunderstood as only being associated with horrible criminals or violent maniacs.

“Psychopathy is a personality disorder where a person shows a profound lack of empathy for the feelings of others,” discloses Keyl. “Physiologically, psychopaths have a brain impairment that allows them to lie convincingly because they do not experience fear and anxiety in the same way the rest of us do.”

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Keyl goes on to reveal that many psychopaths represent an interesting duality: They can act with extreme callousness but present themselves as warm, charming, and eminently believable. In short, they have the ability to tell big lies and not feel nervous about it, Keyl says, meaning they can “pull off cons and frauds better than the rest of us.”

To Catch Them (If You Can)

Any talk of wild deception will inevitably bring up the story of Frank Abagnale Jr., the teen who fooled many while pretending to be a doctor, a lawyer, and an airline pilot, and whose story became the Steven Spielberg film Catch Me If You Can. Despite Abagnale’s masterful ability to forge documents and gain people’s trust, he was eventually caught by authorities in France.

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Indeed, each one of these well-known frauds was found out and brought to some level of justice. But some lies are uncovered sooner than others—so how exactly do these individuals end up getting caught?

Keyl explains that liars usually have certain cues that we can pick up on: “Oaths are something that liars tend to do more than truth tellers.”

So what does that mean, exactly? It means liars will lean heavily on ubiquitous affirmations of truth, like “I swear to God,” or “I say this on my mother’s life,” or the quick but emphatic, “Believe me!” According to Keyl, these phrases are used to manage the perception of those being lied to, so liars will use them with much more regularity than the average honest person.

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There are plenty of other verbal cues to look for if you think you’re getting your leg pulled. Popple warns that someone with something to hide is more likely to pepper their untruth with an excessive amount of specificity to cover their tracks: “People who lie give too many details about the lie.” He gives the example of people who find their credibility questioned and then go on and on, giving all the reasons why they should be believed. “If someone asks me about my PhD,” Popple says, “I’m not going to go over every course I ever took.”

“Chutzpah”

As detrimental as lies can be to other people’s lives when weaponized or used for ill-gain, there is another side to some frauds: a sense of awe that we have as a society have for those who can pull off such feats of deception. It’s exactly why Frank Abagnale’s story is so well-known or why Hollywood loves a good con man story or heist film.

Jaffa, who loves to spin yarns and promises his moments of untruthfulness are all in fun, distills the reason we are so fascinated by those who lie to one simple word: “Chutzpah.”

The word chutzpah, derived from Yiddish, means to have the nerve, the gall, the audacity to do something few would do. Jaffa wears the term as a badge of honor, even going as far as getting it on his custom license plate. To him, it means having confidence in yourself and taking a leap of faith that others will be so charmed or impressed by you, they won’t think to second guess you.

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In fact, Jaffa considers himself such an expert in the world of chutzpah that he taught a class on it in the 1980s (and, unlike many of Jaffa’s claims, this one is absolutely true). It’s all based around the idea that the right amount of chutzpah can compel you to ask for a raise or nab a better table at a restaurant. It allows a regular schmo to get backstage to a concert with the right story and attitude. In this case, a little lie can be a good thing.

The Slippery Truth

When asked about the idea of lying for fun, Popple says there is a “thrill” that comes with getting away with something. Some people have a very high threshold for what can get their adrenaline going, and those people usually end up being the most egregious liars. Popple also shares this opinion: “Everybody’s behavior makes sense to them and brings them some benefit.”

In the case of Jaffa and his tall tales to strangers, it might be that Jaffa’s stories bring a little excitement into the lives of others, but it certainly brings Jaffa some emotional benefits as well.

The truth can be a funny thing. Popple says his father looked like football player Fran Tarkenton, and when asked for autographs, he would just oblige rather than explain he wasn’t who folks thought he was.

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Jaffa tells stories of being on the phone, getting “recognized” as George Clooney, and running with it. Are such lies harmless? Or is any untruth an assault on decency?

Ultimately, there is surely something impressive about the huckster who gets away with pulling one over on others. Whether that person has crossed the line is all in defining where the line is.

One thing is certain, though: If you ever see a man roll up in a car with a license plate reading “CHUTZPA,” you would be well advised to take whatever he says with a huge grain of salt.