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Howard Lederer lived in a family of five where he loved gambling on numerous card games at a young age. He discovered himself getting really competitive in these particular card games as he was competing against his father. After finishing high school, Howard made a decision to put higher education on hold for a little while and relocated to New York to participate in some big-time chess. While competing in chess, he was brought in to a poker game going on in the rear of the room. Howard's first 2 years were tough as he would play many hours and do not win a majority of the time. He earned some additional cash by being an assistant for the poker players. He theorized he could boost his game by balancing his life outside of poker. He brought about an effort to acquire more sleep and focus even more on poker.

The real advancement in his game happened when he began gambling at the Mayfair Club in New York. The Mayfair was a bridge and backgammon club where the the most favorable gamblers would regularly challenge each other. He had access into some of the foremost minds in chess. With their help, he would sharpen his logical thinking abilities. He used these strategic concepts in the game of NL holdem.

Howard also helped his sister Annie Duke learn poker. She was an excellent student of the game as she constantly asked questions about the right way to make the correct choice. He told Annie Duke to head out to Vegas and compete in the WSOP tournaments. She is one of the best female players the poker world ever. Howard moved to Sin City in 1993 and competed in money games for the next decade. When the World Poker Tournament grew in popularity, Howard decided to play more tournaments.