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I am a huge fan of Ayoob's, but personally I think In the Gravest Extreme is the one book to give to somebody who has already decided to own a gun. I haven't read his Role of the Firearm in personal Protection, but it could certainly qualify.
Overall, though, if you are honestly talking about somebody who is on the verge of switching between emotionalism and rationalism in considering gun control, Lott's book seems like the place to start.
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“What is a moderate interpretation of [the Constitution]? Halfway between what it says and [...] what you want it to say?” —Justice Antonin Scalia
SIG: P220R SS Elite SAO, P220R SAO, P220R Carry SRT, P226, P239 (.40S&W), P2022 (.40S&W); GSR 5", P6.
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