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Howard Lederer lived in a family of five where he enjoyed playing different card games when he was young. He found himself becoming very competitive in the above-mentioned card games as he was competing against his father. After finishing secondary school, Howard made a decision to place higher education on hold for a bit and moved to New York City to play some formidable chess. While participating in chess, he was introduced to a poker game going on in the back of the room. Howard's initial two years were tough as he would play countless hours and do not win most times. He earned some extra money by becoming an assistant for the poker players. He theorized he possibly could better his game by analyzing his life outside of poker. He brought about an attempt to get more sleep and concentrate more on poker.

The real advancement in his skills began when he began betting at the Mayfair Club in New York. The Mayfair was a bridge and backgammon club where the best gamblers would regularly challenge one another. Howard had access into several of the greatest players in chess. With their assistance, Howard Lederer would tweak his cunning thinking abilities. He used these strategy ideas in the game of No-Limit hold'em.

He also helped his sibling Annie Duke learn the game of poker. Annie Duke was an excellent student of the game as she constantly asked questions about how to make the correct choice. He told Annie Duke to head out to Las Vegas and compete in the World Series of Poker competition. She is one of the best female players the poker world ever. Howard Lederer moved to Vegas in 1993 and played money games for the next 10 years. When the World Poker Tournament gained popularity, he made the decision to participate in more tournaments.