On 2 June 1763, Ojibwe warriors executed one of the most audacious military captures in North American history. Using a lacrosse match as cover, they took Fort Michilimackinac during Pontiac’s War, a coordinated Indigenous resistance against British colonial expansion across the Great Lakes. The fort fell not through siege, but through patient planning and brilliant tactics. Nearly 150 years later, on the same date in 1910, Charles Rolls became the first person to fly across the English Channel and back without landing. The co-founder of Rolls-Royce completed the double crossing in 95 minutes, piloting a Wright biplane with just 35 horsepower. Tragically, he died in a flying accident weeks later, aged 32. Two events, separated by a century and a half, united by audacity and the willingness to attempt what looked impossible. Sometimes the move that shouldn’t work is exactly the one that does.