The military leader who famously crossed the Alps with elephants was Hannibal Barca. During the Second Punic War, which was fought between Carthage and Rome from 218 to 201 BCE, Hannibal orchestrated a daring and strategic military campaign. In 218 BCE, he led a diverse army, including war elephants, across the treacherous terrain of the Alps in a bold attempt to invade Italy from the north. This maneuver shocked the Romans and allowed Hannibal to win several significant battles on Italian soil. His crossing of the Alps has become emblematic of military ingenuity and determination, showcasing his status as one of history's great tacticians.