While not as well known as other names on this list, Cowkeeper (aka Ahaya) was truly hardcore and one of the earliest known leaders of the Seminole tribe. When early Spaniards began attacking Indian settlements, he began raiding right back at them. He loathed the Spanish so much, he believed the only way to the afterlife was to kill 100 of them. However, his bloodlust didn’t extend to the British, who respected his tribes rebellious spirit. In 1783, after falling ill, he confessed that he had only killed 86 Spaniards and asked his sons to kill 15 in his name.