Hannibal was brilliant, stubborn, and incredibly charismatic. His ability to not only take advantage of the different national troops in his army and use their strength in an over arching strategy while keeping them united was key to his success.
The toughest decision in his life was deciding not to march on Rome against the advice of his other advisors, but it was likely a smart move. He had lost a great many experienced men at Cannae, he also had a shaky supply line and thus couldn't really risk a protracted siege against Rome.
A bloody siege of Rome over the span of weeks probably would have broken the resolve of his army and split his coalition.
Like the American's after Desert Storm, Hannibal never really had a post Cannae battle plan except to cause havoc, try to draw the Roman's into another structured battle and hope that Rome fell on its own. He didn't get those results, instead Rome had a chance to reform and rebuild its army, went back to avoiding major battles and bloodied Hannibal where he could, and eventually push Hannibal back to Carthage.
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My name is Ozymandias, King of Kings;
Look on my Works, ye Mighty, and despair!
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