Hannibal
The Carthaginian general who marched elephants over the Alps and shattered Rome's armies at Cannae, yet could never take the city and lost the war.

In the summer of 216 BCE, on a plain in southern Italy called Cannae, a Carthaginian general destroyed the largest army Rome had ever put in the field. By some ancient counts as many as seventy thousand Romans died in a single day, killed by a smaller force that had let its center fall back and then closed its wings around them like a pair of jaws. The man who built that trap was Hannibal Barca, and Cannae is still taught in war colleges.
The oath and the Alps
Hannibal was raised on hatred of Rome. His father Hamilcar, a Carthaginian commander in the First Punic War, is said to have made the boy swear at an altar that he would never be a friend to Rome. In 218 BCE Hannibal made good on it with one of the most audacious marches in history: he took an army out of Spain, over the Pyrenees, across the Rhone, and through the snowbound passes of the Alps, war elephants and all, to fall on Italy from the north where Rome least expected him. He lost thousands of men and most of the elephants on the way, and it did not matter.
Victories that led nowhere
Over three years he beat Rome again and again: at the Trebia, at Lake Trasimene where he ambushed and drowned a consul's whole army, and above all at Cannae. For a decade and a half he ranged across Italy, undefeated in open battle, and still the war slipped away from him. He could never take Rome itself. He had no siege train, little reliable support from a jealous home government, and an enemy that simply refused to negotiate no matter how many armies it lost, raising fresh legions and avoiding open battle under the general Fabius, whose delaying strategy gave us the word Fabian. Hannibal won the battles and slowly lost the war.
Zama and the long defeat
In 202 BCE Rome carried the fight to Africa, and Hannibal was recalled to defend Carthage. At Zama he faced a Roman general who had studied his methods, Scipio, later called Africanus, who neutralized the elephants and turned Carthage's cavalry weakness against it. Hannibal lost. He spent his last years as a hunted exile in the courts of Rome's eastern enemies, and around 183 BCE, cornered by Roman agents in a town in Bithynia near the Sea of Marmara, he took poison rather than be handed over.
The verdict of history is strange for a man who lost. Hannibal ad portas, Hannibal at the gates, survived in Latin as the phrase Roman parents used to frighten children for centuries, and his double envelopment at Cannae remains the textbook picture of a perfect battle, the one every general since has tried, and mostly failed, to repeat.