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Jadakiss, became a freestyler, engaging in competitions by the time he was twelve.
He and some of his early friends were given the opportunity to compete in the Jack the Rapper Competition in Florida, where Jadakiss was noticed for his battle rap ability.
He met Dee and Wah of the Ruff Ryders, then a management company, and began hanging out and battling outside of the Ruff Ryders' studio where artists like DMX made their first hits.