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Howard Lederer lived in a family of 5 in which he enjoyed playing different card games at a young age. He discovered himself getting really aggressive in these particular card games while competing against his dad. After graduating from Sr. High school, Howard decided to put higher education on hold for a little bit and moved away to New York City to compete in some formidable chess. While playing chess, he was introduced to a poker game taking place in the rear of the room. Howard's initial 2 years were difficult as he would play countless hours and fail to win most times. He made some extra cash by being an assistant for the poker players. He judged he could boost his game by adjusting his life outside of poker. He made an effort to acquire more rest and concentrate even more on poker.

The real advancement in his abilities began when he began wagering at the Mayfair Club in New York City. The Mayfair was a bridge and backgammon club where the best players would regularly challenge one another. He had access into several of the best minds in chess. With their assistance, Howard would sharpen his strategic thinking techniques. Howard used these strategic ideas in the game of NL hold'em.

Howard also assisted his sibling Annie Duke master the game of poker. Annie was an excellent student of poker as she would always be asking questions about how to make the proper decision. He told Annie Duke to move out to Las Vegas and compete in the WSOP competition. Annie is one of the best women players the poker world ever. Howard relocated to Sin City in 1993 and participated in cash games for the subsequent decade. When the World Poker Tournament gained popularity, Howard decided to play more tournaments.