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Howard Lederer lived in a family of five where he liked playing different card games when he was young. He discovered himself becoming really aggressive in these card games as he was playing his father. After finishing high school, Howard made a decision to put higher education on hold for a bit and moved to New York City to compete in some big-time chess. While competing in chess, he was introduced to a poker game going on in the back of the room. Howard's first two years were difficult as he played countless hours and lose a majority of the time. He earned some additional cash by becoming an runner for the poker enthusiasts. He theorized he could improve his game by adjusting his life away from poker. He made an effort to get more sleep and focus even more on poker.

The actual advancement in his game happened when he started gambling at the Mayfair Club in New York City. The Mayfair was a bridge and backgammon association where the best gamblers would regularly challenge one another. He was able to access some of the greatest players in chess. With their assistance, he would hone his strategic thinking techniques. Howard applied these strategy ideas to the game of No-Limit texas hold'em.

He also assisted his sister Annie Duke learn poker. She was a great student of poker as she constantly asked questions about the right way to make the correct decision. Howard told Annie Duke to head out to Las Vegas and play in the World Series of Poker tournaments. She is one of the greatest women players the poker arena has ever seen. Howard relocated to Vegas in Nineteen Ninety Three and competed in money games for the subsequent 10 years. When the World Poker Tournament gained popularity, Howard decided to play more tournaments.