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Born in Crab Orchard, Kentucky, Smith ran away from home as a teenager to work on a flatboat on the Mississippi River until reaching St. Louis, Missouri where he began working for John Jacob Astor as a fur trapper with other mountain men such as Kit Carson, Jim Bridger, and Milton Sublette.
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Pegleg Smith and his cohorts entered Southern California to steal horses from the Spanish ranchos.
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After leading a wild and adventurous life, Pegleg Smith died in San Francisco a poor drunk.