From Damn Interesting:
In 1940, some of the German commanders who were overseeing the push into France began to receive seemingly random reports of soldiers having been killed with broad-head arrows or hacked with a English Claymore. Effective enough weapons it would seem, but archaic even in that day and age. They likely could have guessed the bowman was an English soldier, but they couldnâ€™t have appreciated these as the calling card of the rabid eccentric, Captain Jack Churchill.
In another attack Mad Jack and one of his enlisted men managed to sneak up on a pair of German sentries making rounds. He leapt at them, sword in hand and shouted, â€œhaende hoch!â€ The Germans obeyed by dropping weapons and raising their hands. One sentry was taken back to camp while the other had Jackâ€™s belt wrapped round his throat, and together they continued the rounds. At each guard post his prisoner would say something to lull the guards into complacency, then a mustached-mad-man with a sword would jump out and order them to drop their arms. All in all, the two Brits rounded up forty-two prisoners that night.
And from his Wiki entry comes this gem:
Eccentric until the end, Churchill would toss his briefcase out of the window of the commuter train he rode home every day. Passengers and conductors were shocked because they didn’t know he was throwing the luggage into his own backyard as the train passed by. It saved him the trouble of carrying it all the way home from the station.