We tend to think of Washington as an invincible leader and the “father of his country,” but he had his weaknesses. Known for his bravery and big-picture strategic thinking, Washington struggled when it came to planning and executing the details necessary to achieve victory on the battlefield.
“If you look at his win-loss record, it’s not great,” Hensinger says. “He loses more battles than he wins.”
Often, Washington overestimated his ability to execute complex maneuvers that required precise timing. This tendency almost derailed the Continental Army’s December 1776 victory at the Battle of Trenton, in New Jersey—which you might know as Washington’s famous “crossing of the Delaware.” Washington had cooked up a complicated plan that required his army to split up and cross the Delaware River at three different points and march varying distances to arrive at Trenton at the same time, Hensinger says.
There, they would attack the Hessians, German troops helping the British, from multiple sides.
But the strategy fell apart, with only Washington’s group making it to the meeting point.
Ultimately, Washington won the battle owing to tactical mistakes by the Hessians, an outcome that turned the tide in favor of the Continental Army. But it all could have gone sideways “if just a few things had gone differently,” Hesinger says.