Washington - Crossing the Delaware
During the American Revolution, George Washington had the most difficult mission as a General: keeping a "ragtag" army of volunteers going for eight years. Some of his soldiers enrolled for six months, a year or two. Which means he had to train new recruits constantly.
With this in mind, one understands more easily he could not take risks on the battlefield, any defeat could prove fatal on the morale of men and the support of the newborn Congress. Yet, in December 1776, General George Washington did take a gamble!
On the night following Christmas, he and his army crossed the Delaware river to surprise the British soldiers who never thought in a million years they could be attacked on such Holiday! Having drunk all night, they were nowhere near ready for combat the next morning... Way to go General Washington!