George Washington

What failed

His first independent command ended in surrender at Fort Necessity in July 1754. A year later he was with Braddock's expedition when it was destroyed at the Monongahela, with 977 of 1,459 men killed or wounded. He spent years pursuing a regular commission in the British army and never got one. Then, commanding the Continental Army, he lost New York — beaten at Long Island in August 1776 and losing the entire garrison of Fort Washington that November — then lost Brandywine, which handed the British Philadelphia, then lost Germantown when his own attack collapsed in fog and friendly fire.

What happened next

He kept the army in existence, which was the actual job, and in October 1781 the siege of Yorktown ended the war.

The point

Mount Vernon, his own historic site, puts it plainly: he lost more battles than he won. It gives no number, and neither does anyone reputable, because the count depends on what you decide to call a battle. The point stands without arithmetic — the man who won the war was not the man who won the most fights.