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The greatest mistake perhaps was when he chose not to besiege Rome but go around and try recruit more soldiers during his time in Italy. Rome took that opportunity to send soldiers to Carthage and Hispania (what is now North Africa and Spain) and thereby forcing Hannibal to return to Carthage and fight the battle of Zama which he lost. If he had beseiged Rome, he might have won and even if he didn't, it would still somehow influence the course of history for beseiging Rome would've kept second Punic War to last longer (for example, beseiging Rome might prevent messengers, orders or soldiers from Rome to leave for other places like Carthage and Hispania and thereby preventing the Battle of Zama to even happen perhaps).

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Q: What was Hannibals greatest mistake?
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