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Howard Lederer was born into in a family of five where he liked betting on numerous card games when he was young. He found himself getting very competitive in the above-mentioned card games as he was competing against his father. After finishing high school, Howard decided to put higher education on hold for a little bit and headed to New York to compete in some big-time chess. While competing in chess, he was introduced to a poker game taking place in the rear of the room. Howard's first 2 years were tough as he would play many hours and lose most times. He earned some extra cash by being an assistant for the poker enthusiasts. He judged he might better his game by balancing his life away from poker. He made an effort to get more rest and focus more on the game.

The real improvement in his skills happened when he began playing at the Mayfair Club in New York. The Mayfair was a bridge and backgammon club where the best gamblers would often wager against each other. He was able to access some of the greatest minds in chess. With their assistance, Howard would sharpen his strategic thinking skills. He used these strategy ideas in the game of NL holdem.

He also assisted his sibling Annie Duke learn poker. She was an excellent student of the game as she would consistently be asking questions about the right way to make the correct choice. He told Annie to head out to Sin City and compete in the World Series of Poker tournaments. Annie is one of the greatest women players the poker world today. He relocated to Sin City in 1993 and participated in cash games for the following 10 years. When the WPT grew in popularity, Howard made the decision to participate in more tournaments.