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Cheaters Always Win: The Story of America

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A social history of cheating and how American history -- through real estate, sports, finance, academics, and of course politics -- has had its unfair share of rigged results and widened the margins on its gray areas.


Drawing from the intriguing (and sometimes unbelievable) true stories of the lives of everyday Americans, historian Julie M. Fenster traces the history of the weakening of our national ethics through the practice of cheating. From marital infidelity to financial fraud; rigged sports competitions to corruption in politics and the American education system; nuclear weaponry to beauty pageants; hospitals, TV gameshows, and charities; nothing and no one is exempt.




And far from being ostracized, cheaters in every sphere continue to survive and even thrive, casting their influence over the rest of our society. And nowhere is this more obvious than in the recent tectonic shift in politics, where a revolution in our collective attitude toward fraudsters has ushered in a new kind of leadership.




Part history of an all-American tradition, part dissection of an ongoing national crisis, Cheaters Always Win is irresistible reading -- a smart, sardonic, and scintillating look into the practice that made America what it is today.

272 pages, Hardcover

Published December 3, 2019

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J.M. Fenster

3 books8 followers

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5 stars
7 (5%)
4 stars
24 (17%)
3 stars
53 (38%)
2 stars
37 (27%)
1 star
15 (11%)
Displaying 1 - 30 of 32 reviews
Profile Image for Kusaimamekirai.
712 reviews270 followers
July 18, 2020
What motivates the cheater? Why do they seem so prevent particularly in the United States?
More importantly, why are the cheated so unwilling to “snitch” on the people cheating?
These questions and more are raised in this short but fun little survey of America’s favorite pastime.
The answers?
Well, they are seemingly as elusive as the cheaters themselves.
Be it infidelity, sports, academia, or any other facet of human life, people have myriad reasons and motivations.
Lack good moral instruction from your mom? One study says this is why you cheat. Another says, “that’s nonsense”.
Cheating on your exams? It’s fine because once I get that diploma from this school that i just need a diploma from, I’ll stop cheating.
Except when they don’t.
Hello financial institutions littered with people from MBA programs!
The most interesting aspect of the book perhaps is why when we see cheating, we don’t speak up. The author hypothesizes that there is a kind of unspoken bond between the cheater and the cheated that prevents us from being the one to stand up and by extension, stand out.
Be it because of embarrassment that someone got over on us, respect that they were sophisticated enough to pull it off, or simple indifference, Fenster argues that cheating proliferates in societies where people stay silent.
He comes just sort of blaming the cheated but he has a point. The immoral will always be that way. As the saying goes, if you give a chimp a gun and he shoots someone, you don’t blame the chimp.
In the same vein, if we are ever going to reclaim integrity for society (a tall task to be sure in America circa 2020) it is incumbent on the cheated to find their voice and call out cheating wherever it’s found.
Profile Image for Jeremy Lucas.
Author 13 books5 followers
August 30, 2020
If you’ve ever read a book filled with pages that didn’t matter, pages that held no narrative, no string or theme worth tracking as a reader, then you can understand what reading this book feels like. I won’t say it was entirely grueling, because I found a handful of amusing anecdotes and some unfair assumptions that made me speak audibly to the book, but I picked this title up thinking I would get a traceable account of cheating throughout American history, like a series of stories that moved at pace with the nation as it formed, grew, and emerged under Donald Trump, some 250 years later. What I got, instead, was Fenster’s individual philosophy of cheating, informed by stories she knows, and a few she found. Nothing comprehensive and certainly nothing sound. Ho hum.
Profile Image for Alexandra.
669 reviews44 followers
July 14, 2020
I listened to about half of the audiobook before giving up. It sounded like an interesting read, and it had its moments. But it was boring, seemed to jump around a lot, and just seemed a little unorganized at times.
Profile Image for Heather.
441 reviews15 followers
December 17, 2020
Anecdotal, jumpy, random, but generally enjoyable
37 reviews4 followers
December 15, 2019
A truly engrossing read that well supports the title proposition. The kind of "public intellectual" book the publishing industry could do well to support more.
1,581 reviews39 followers
December 20, 2019
funny, fairly random, asssembly of anecdotes about cheaters -- the spitballer Gaylord Perry and the subway-taking "marathoner" Rosie Ruiz perhaps the most famous from the world of sports. student plagiarists, bridge players with methods of communicating with partners about their hands, etc. etc etc. Very breezy in tone. Your mileage may vary, but i mostly enjoyed her sense of humor.
Profile Image for Ietrio.
6,932 reviews24 followers
December 6, 2019
Fenster is not against cheating. Far from it. Only Fenster feels like a loser. And Fenster needs the state to use its spiked club to do the cheating for the losers.
88 reviews2 followers
December 28, 2020
So many disjointed anecdotes about random people's experience with cheating. I don't really care about the person who stole a penny piece of gum. Give me substance or give me death.
422 reviews3 followers
January 12, 2021
Really disorganized book and a frustrating read by the end of it. Unclear as to what the main point of the book is, and how all the different sections connect (or don't) to each other.
Profile Image for John McDonald.
600 reviews23 followers
March 7, 2020
Not everybody cheats, or at least not everybody who cheats does so intentionally, suggesting, too, there may be competing definitions. Some people cheat once or once in a while and then stop. And although the author, in her title and throughout the book wants you to believe, cheaters most certainly do not always win, e.g Bernie Madoff, Pete Rose, to name two as well as those cited in the book.

Cheating is a serious subject, and at times, I thought the author was dismissive, surly, and sarcastic about her subject to the point that I thought she wrote the book just to get the publisher or her agent off her back, something herself suggested in the book. Her humor or attempts at it become weak of expressions of needing to write something further, i.e. not funny. She also missed one obvious character flaw in the recidivist or serial cheater, the sin of hubris, the only sin the ancient Greeks believed, was uniformly punished by their gods because it suggested that morals could do or perform the very tasks those gods commanded only be performed by themselves.

Most readers readily will recognize the anecdote the author tells of cheaters who succeeded.
There was only 1 example new to me, that of the college football player convicted of cheating his college's student honor court, expelled from school, and his football career and college degree gone up in smoke. The sad part of that--the really telling part of that story--was that this outstanding athlete was advised by Rick Pitino who as he has done multiple times in his career managed to weasel around it. The author states: "People who never see the rest of the world except as a satellite of their own universe can't perceive that they cheat . . . it is obvious to them that the rest of the world cheats". She could have added the word, "too" at the end of that sentence, because that is how cheaters justify their conduct. It is also how they get caught.

Much is made of cheating in marriage which is a problem for those who engage in it. But most people do not cheat on their spouses, even if they may think about it or threaten it in a severe marital argument, maybe because when they give it some thought they understand first, how much work it is to cheat successfully, how low the odds of doing it successfully, or the consequences if caught.

Even though it is a reminder by implication, there is an important suggestion in this book that cheating requires the exacting of a very heavy unwanted financial or emotional cost to someone else. Not all of us cheat. Some of us will never cheat because we paid attention to parents, teachers, rabbis, priests, nuns who told us God was watching and that it is wrong whether or not he or anyone else saw us cheat. And, it is obvious to me, having observed the phenomenon throughout my life, that money or adventurous sex pose the greatest risk to become a cheater or remain a cheater. Getting away with it so that one feels comfortable doing it repeatedly in the same fashion brings us right back to hubris.
Profile Image for Squirrel.
424 reviews14 followers
September 23, 2021
I feel cheated out of 6 hours of my life and I think that the library I borrowed this from was bilked of a significant amount of money for this book. The other reviewers are correct: this is poorly structured and relies on many spurious assumptions and a shallow analysis of the subject.
Case in point: the author uses one study of students' reasons for getting a college degree, in which a few hundred random college students are asked the same question about why they are getting a degree. Over time, from the 1970s to the present, far more students are getting the degree with the hope of becoming well off, rather than for subject mastery or or to discover more about themselves. Fenster then postulates that it's this desire to get wealthy that is prompting the rise in cheating because students in search of pure knowledge have less motivation to cheat in order to get the diploma. This seems like a lot of leaps of logic, but Fenster goes on to base a lot of her assertions on this fact.
Fenster fails to take into account any external forces that might cause that rise, such as the defunding of public universities causing students from the 70s on to take on exceedingly large loans in order to obtain a diploma that has become a necessity in a post-industrial United States. Who else would go to college in these circumstances besides people who viewed the degree as an investment? This use of one study is not quite the slam dunk evidence that the author thinks it is.
Also my grammar might suck according to Ms. Fenster, but at least I didn't assert in a published work that human genetics has been at a standstill for the last 10,000 years. I was also surprised that more game theory, such as the prisoners' dilemma, wasn't included.
All in all, while some of the anecdotes are interesting, the the tone of the work is overwhelming smugly superior with an overemphasis on the moral rectitude of the individuals who decide not to cheat over the sociological forces that push people into spaces where cheating is the only way out.
184 reviews
January 13, 2020
An interesting overview of cheating in America: how it has become so common in daily life and why. The author provides some interesting examples and interjects her personal style of sardonic humor, which adds to the reader's enjoyment. However, Fenster spends an inordinate amount of time on cheating spouses, and digresses in her writing for her own pleasure making it hard to follow her at times. For a book published in 2019, she could have easily added commentary on contemporary items like the college admission scandal, the ACA debacle (you can keep your doctor...), etc. - there are many examples; choose your own favorites - to make the book more interesting. Her big reveal is in explaining why cheaters are winning, and she hits the target. Read it and see for yourself.

A good companion book is Who Killed Civil Society? by Howard Husock.
Profile Image for Robert K.
135 reviews1 follower
March 17, 2020
A clever collection of stories of cheating in society. It’s one of those books that has you thinking “...should I admit that this topic interests me...”. Well, the topic fascinates me because perhaps because I’m mischievous at heart not thankfully because I condone the practice. Regardless, some of the examples cited by the author are just mind blowing & audaciously interesting to read. It is a book that has a person rechecking his or her moral compass & for that alone I recommend it as time well spent.
Profile Image for Katie.
95 reviews4 followers
August 21, 2021
Certainly not a scholarly endeavor, but a funny one—read it for the entertainment value. Too bad the Lori Laughlin college cheating scandal happened after this, I feel like Fenster would’ve had a field day with that. And she definitely missed not having a chapter on how George Washington and all the founders cheated Black and Native Americans.
77 reviews
January 18, 2022
Mainly just filled with anecdotal cheating stories. I was expecting a more comprehensive review of cheating in American history, studies on why people cheat, and perhaps a few examples to drive the points home. It's pretty much just individual stories, mixed with way too much of the author's inner dialogue and attempts to be funny in places that don't call for it.
Profile Image for Michele.
150 reviews
April 5, 2021
Little vignettes of cheaters and how we let them get away with cheating. Not super comprehensive, since it's only 217 pages for the book (besides the acknowledgment and index). Fun and interesting though.
Profile Image for Nicholas Galinaitis.
87 reviews6 followers
November 29, 2022
Eye opening and entertaining! Wasn't always a fan of the writing style but the thesis that America is a country that glorifies cheating and shortcuts really made me think 🤔 not sure if I agree with everything but definitely some interesting historical stories in here.
1 review
December 11, 2019
Great stories, read it in two days, and there's a point. It' an original take on what happened to ethics in marriage, sports etc.
Profile Image for Tai Odunsi.
Author 6 books51 followers
January 20, 2020
well written...so much so, it's artful prose gets in the way of what should have been a simple layout of the age's rich variety of cheaters
Profile Image for John Miller.
50 reviews1 follower
February 6, 2020
Interesting premise, cheating is driven by those of us who accept cheating in society, not necessarily the cheaters themselves
Profile Image for Suzanne.
85 reviews9 followers
April 19, 2020
I see why only 3 stars and yet I ended up enjoying this book very much. Mostly because the wry amusement of the authors jaundiced view of humanity came through in sometimes unexpected places.
Profile Image for Melanie.
915 reviews60 followers
did-not-finish
August 28, 2020
Boring and disjointed. Gave up a couple chapters in.
Profile Image for Haidong.
166 reviews
August 8, 2021
Just as other reader said this book was poorly written, no coherent central theme, lots of repetitive phrases in the book without any apparent meaning, suggest to pass.
392 reviews
November 30, 2021
It was hard for me to get into this book, as it had elements of psychology mixed in with history. As I have no background in psych, it was a difficult read.
44 reviews1 follower
April 6, 2022
Sounded like a fun book but she started out berating the former president and I realized it is probably a socialist hack job. I made it through 2 chapters then fell asleep.
104 reviews1 follower
July 22, 2020
Excellent read on society and how we accept some cheating things but not others.
Displaying 1 - 30 of 32 reviews

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