Hannibal
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Hannibal was a Carthaginian commander and military genius. He was the son of the general Hamilcar Barca. During the Second Punic War against Rome, he crossed the Alps with 38 War Elephants in a mere 15 days to surprise the Roman armies. Winning battle after battle, including killing 60,000 Romans in a single day at the Battle of Cannae, he still lost the war when the Romans could replenish their losses with deep manpower reserves that Carthage didn't have. Feared and succesful even in peace, the Romans eventually forced him to commit suicide in 183 BC.
He decided to attempt to take over the Iberian Peninsula (where Spain is today) by crossing it with 50,000 infantry, 9,000 cavalry, and 37 elephants. [1]