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  2. How to Win Arguments
July 11, 2026 at 9:33 AM

How to Win Arguments

iWe
@iWe

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We all know how to lose an argument. The first mistake is to allow the enemy to define the battlefield. "Why do you beat your wife?"

The second mistake is to think that compromise is a universally good outcome: "Let's kill all the Jews" just becomes "Let's kill half the Jews."

The way to win an argument is by asking the penetrating question. In this way, you can define the terms, shape the battlefield, and expose the silliness of the opposition's position. The great master at this was Milton Friedman, who discussed the Ford Pinto against a student who, it must be said, was clearly much brighter and better-spoken than just about any young liberal today. The defense is here. Friedman did it by asking questions. And he proved the principle, beautifully,

The Socratic method works. We should be using it more and more, especially with hostile audiences and interviewers.

I was reminded of this when I read this beautifully written piece about a single Israeli invited to a dinner party where he would be attacked by everyone there. His writing is loquacious and entertaining. The debate was certainly engaging. But this Israeli was always fighting a rear-guard action. He scored points, but he failed. Utterly. And he did it by descending into the mud pit with the pig and ultimately resorting to insulting his audience for being ignorant. They certainly were, but he won nothing by pointing it out.

He should have started by asking questions. I would have kicked off with: "Is raping and murdering women and babies who belong to a group that you do not like ever justified?" Or, "What should be done with the 600,000 Jewish refugees who were forcibly expelled from Arab lands in 1948?" Or, "Why are you not giving your apartment back to the Native Americans from whom your ancestors stole it?"

Then you set the trap. Keep asking questions. Expose the ignorance and idiocy. Win the argument.

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Discussion (14)

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    Jimmy Carter@JimmyCarter·16w

    I learned this tactic reading Aristotle's De Anima.
    He states He wanted to be a midwife to people's thoughts.

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    Zafar@Zafar·16w

    Is there a way to still win if the other person ask you that penetrating question?

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    Subcomandante America@TheReticulator·16w

    I don't understand this concept of winning an argument. Is it anything like a rubber duck?

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    iWe@iWe·16w
    ReplyingtoZafar

    Zafar (View Comment):

    Is there a way to still win if the other person ask you that penetrating question?

    The choice of battlefield makes up an awfully-large part of victory.

    It is why "Pro-Choice" is used for abortion advocacy instead of "Pro-Death."

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    Zafar@Zafar·16w
    ReplyingtoiWe

    Zafar (View Comment):

    Is there a way to still win if the other person ask you that penetrating question?

    iWe (View Comment):

    The choice of battlefield makes up an awfully-large part of victory.

    What if 'they' get in first? Can you still win? Or is it all about getting in first and defining the conflict?

    If they get in first do you need to ignore their question and talk over them or is there a way of engaging with their [penetrating question] that still leads to victory?

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