Freakonomics and the Weird Psychology of Losing on Purpose

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Okay, so I’ve been thinking about this book Freakonomics by Levitt and Dubner. There’s this concept that’s been messing with my head for weeks now “cheating to lose.”

Like, what? That doesn’t even make sense at first, right? We’re wired to think cheating is about winning getting ahead. However, these guys flip the whole thing upside down and… honestly, once you see it, you can’t unsee it.

Here’s what I’m getting at: people don’t just cheat to win. Occasionally and this is the part that’s gonna sound crazy they cheat to lose strategically. When the system is so screwed up that losing actually gets you more than winning would, everything changes.

Teachers Are Breaking My Heart Here

Let me start with the teachers thing because it’s honestly depressing as hell. The book talks about Chicago public school teachers who got caught changing their students’ test answers. My first reaction was like, “okay, typical cheating scandal, teachers trying to make themselves look good.”

Freakonomics and the Weird Psychology of Losing on Purpose in public education

But wait that’s not what really happened.

These teachers didn’t change answers for glory or bonuses (though those exist). They did it because they feared losing their jobs. The whole system punishes you if your kids don’t hit the numbers. It doesn’t matter whether you’re teaching in an underfunded school where kids deal with poverty or family issues.

So, they weren’t cheating to win they were trying to survive. And that hits differently, you know? It really makes you wonder who the real villain is here.

Wait, Sumo Wrestling Gets Weird Too

This one blew my mind. In Japan, sumo wrestling holds sacred, honorable status. It earns massive cultural respect. Nevertheless, Levitt noticed something unusual in the data.

Picture this: one wrestler has already won 8 matches (he’s safe for the tournament), and he’s facing a guy with 7 wins who desperately needs the 8th win to keep his ranking. So, what happens? The safe guy throws the match. Not out of friendship. Not out of honor. Because it’s smart business.

The secure wrestler can afford to lose. Meanwhile, the guy who needs the win? He now owes a favor. In sumo’s tight-knit community, those favors shape careers.

It’s calculated. It’s strategic. And yes, it’s absolutely cheating to lose.

Actually, This Happens Everywhere in Sports

Actually, now that I think about it, this happens everywhere in sports. Boxers take dives. Teams tank for better draft picks. Athletes fake injuries. Although we don’t usually think of it this way, it’s exactly what “cheating to lose” looks like.

Parents Are… Complicated

Ugh, the parent thing is where it gets really messy. Some wealthy parents literally fake being poor so their kids qualify for need-based scholarships or equity programs. They game the system by pretending to have less.

On the flip side, some kids bomb tests on purpose to stay out of advanced classes. Why? Because those classes mean more pressure, more work, and higher expectations. Choosing underachievement becomes the path of least resistance.

I’m not saying it’s right, but… I kind of get it. The pressure on kids today is insane.

The Movie Example That Actually Made Sense

You know what really clicked for me? The example from Akeelah and the Bee. In the final spelling bee, Akeelah prepares to intentionally miss a word to let Dylan win — because she sees the intense pressure his dad puts on him.

Dylan, however, refuses to accept a charity win. So, they agree to end it in a tie.

This isn’t manipulation for power. Instead, it’s empathy as strategy. They choose to “lose” the individual competition to win something bigger — their integrity, friendship, and the ability to live with themselves.

And honestly? That scene gets me every time.

Here’s Where It Gets Really Dark

Now this is the part that’s been keeping me up at night. The people who master this “cheating to lose” game? They often turn out to be the ones we admire most.

  • Politicians who used shady tactics early in their careers but now preach transparency
  • CEOs who cooked the books on their way up but now earn reputations as visionary leaders
  • Public figures who “stepped down” after scandals only to return stronger as “redeemed” thought leaders

Yes — they cheated. Then came the consequences: they got caught. And finally, they took the strategic loss resignation, public apology, or whatever. After that, they returned as heroes.

And we eat it up. Let’s be honest: we love a redemption story.

The Youth Are Watching All This

What really gets me is how young people observe these “reformed nobles” and think, “okay, so that’s how the game works.” The message becomes: it’s not about playing fair, it’s about playing smart. And if you mess up? Just take your strategic loss and return stronger.

I’m not saying these kids are wrong to notice the pattern. Yet it’s messed up that this is the lesson they’re learning.

What Does This Mean for… Everything?

Look, I don’t think Levitt and Dubner want to make us all nihilists. Instead, they reveal something uncomfortable: our systems often reward the wrong behaviors.

If we want people to act with integrity, we must build systems that reward it. Not just clever gaming of the rules.

The question isn’t just “what’s the right thing to do?” It’s “what does the system actually reward?” And when there’s a gap between those two things… well, that’s where cheating creeps in.

Sometimes Losing Is the Long Game

Here’s what I keep coming back to: not every loss is actually a loss. Sometimes it’s just a move in a bigger game.

The teacher who changes test scores to keep her job? She’s not chasing awards. She’s just trying to protect her livelihood.

The sumo wrestler who throws a match? He’s not abandoning competition. He’s building social capital for future matches.

The public figure who resigns after a scandal? They’re not ending their career. They’re rebranding for a comeback.

It’s strategic. It’s calculated. It’s more common than we want to admit.

I guess what I’m trying to say is… this book changed how I look at basically everything. Every time I see someone “fail” or “lose” now, I wonder: is this really failure? Or is this just part of a bigger plan I can’t see yet?

Maybe that’s paranoid. But maybe it’s just realistic about how the world actually works.

Either way, I can’t stop thinking about it.

Related Reading: How Modern Education Incentivizes Shortcuts

Sources: Freakonomics Official Site, Chicago Tribune: Teacher Cheating Scandal

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