Allan Houston
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Allan Houston was the heir-apparent to the great John Starks for the New York Knicks, and was an instrumental member of the team that went to the 1999 NBA Finals.
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The Knicks eventually signed Houston to a maximum contract extension worth over $20 million per year, and got virtually no return on said investment after he subsequently went through a myriad of injury problems. Between 2003 and his premature retirement in 2005, he missed over 100 games due to injury.
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