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In only second year at Georgia Tech, Kenny was an All-American first team selection in 1991. As a beginner he didn’t fared well under Bill Fitch, though he abandoned the school after his sophomore year as a number two pick in the draft by New Jersey. John Starks of the Knicks fouled him openly in February 1993 which caused him to take a step back in his growth. He also lost the rest of his second season to injury. He was named an all-star in 1994. In 1993-94 he became the highest scoring PG in the league. Kenny finished the season second in the league in assists with 9.4 per game in 1994-95 season. On 19th February 1996, he developed a reputation of a difficult player in NJ and joined Hornets with Gerald Glass for Kendall Gill and Khalid Reeves in a trade. He became a free agent and played out the season as a Hornet. Finally signed with Portland for 50 million over 7 years.


Kenny was sent to Toronto on February 13, 1998 along with Gary Trent, rookie Alvin Williams and 2 draft picks for Damon Stoudamire, Walt Williams and Carlos Rogers. Kenny stated that he wouldn't play north of the border, and sure enough, he never showed up in Toronto. He was sent to Boston On 18TH February. He penetrates deeply in the sport but is not a reliable threat. He can both shoot the jumper and find the open man. He became east's best point guard due to his passing skills. On February 20, 2002, Seattle traded Kenny Anderson to New Orleans for Elden Campbell. Prior to the 2003-2004 season, Indiana signed Kenny to a free agent contract.