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Oswald Dupont decided at a young age to live the life he always wanted. Ozzy would get the power, the money, the women - whatever he needed to live a comfortable life. Poverty taught him that it was dog eat dog, and his parents being indentured into terrible work via debt kept him on his toes. He harbored some uncomfortable feelings as a kid that he never really grew out of.
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In that sense, Ozzy never grew up - he is still childish, he still tries to take things easy. Treating life like a serious manner only gets you hurt, but taking life the way you want to gives you power over it. He found that it was easier to talk people into doing what you wanted - not empty promises, but real convincing, real charisma.
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The Silvertongue Coven felt like home once he joined up; his talent for smooth-talking and distracting the eye made him a natural at espionage and information gathering, and they had a need for that in the merc world. Ozzy finds himself acting as an information broker in his professional life, something that suits him well; why get himself in danger when others can do that for you? It's worked for him for the last few years, and he sees no need in changing that up anytime soon.