Lieutenant Colonel John Malcolm Thorpe Fleming "Mad Jack" Churchill Where to even start with this guy. Jack Churchill might not fit into this thread that well. He wasn't exactly a grand strategist or a general or anything of that sort. He was merely second in command of the No. 3 Commando unit in the British Royal Army during the second world war. But he was enough of a warrior in the purest sense of the word that I think he bears mentioning. Jack Churchill signed up for the Commandos after fighting at Dunkirk (and surviving being shot in the neck by a German machine gun no less), not really knowing what the Commandos did, but doing so because it "sounded dangerous." During his career as a Commando he basically spent several years of the war riding into battle on a horse armed with naught but a Scottish claymore (the basket hilt kind, not the two-handed Braveheart kind), a longbow (being a champion archer), and a set of fucking bagpipes, which he played regularly. During his career, he led countless Commando raids against German strongholds, leading a string of successful operations, the spirit of which were perhaps best captured in this telegram received by British High Command roughly two hours after a Commando raid on Maaloy Island: On one particular night, Churchill singlehandedly took 42 German prisoners. By himself. With a sword. When questioned about the incident, he responded: During a campaign in Yugoslavia, Churchill was captured by the Germans and placed in Sachsenhausen concentration camp, which he escaped from by crawling under the fence and hopping a train. Then he walked his ass a ways out before being recaptured again and taken to a prison camp in Austria, which he also escaped from. After marching 150 fucking miles, he met up with an American armored battallion. So after that, he attempted to go fight the Japanese in Burma, but the war had ended by the time he got there, much to his disappointment. So he went to Israel to fight the Arabs. Then he got into surfing.