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Leadership doesn't negate luck in any way (I want both). Randomness sometimes turns everything upside down. Recently, in a HotS game with two friends, my Warlock reached level 12 and maxed out the Empathy skill. He received the Leadership skill almost immediately. But by level 16, he couldn't even get the basic Chaos skills. At the same time, he managed to capture an Orcish town. My friends each have one town so far. I just don't know when we'll finish this game, as one of my friends has left for a long time.