He led his team to a New York state championship as a junior before transferring to Oak Hill Academy for his senior season when he was rated as one of the nation's top 10 prep players. He went to DePaul University and became a first-team All-American as a junior and senior and helped DePaul go to four straight NCAA Tournaments. He finished his career averaging 16.6 points per game and had 557 assists and 204 steals. He shot 53.4 percent from the field in his career.
The New York Knicks picked him in the first round and he averaged 8.9 points and 3.9 assists per game his first year while sharing time with Mark Jackson. He was traded to San Antonio and stayed there until the 1992-93 season when he signed as a free agent with Portland and averaged 17 points and 8.6 assists per game over the next four seasons. Strickland was traded to Washington in 1996 and in the 1997-98 season be became only the 25th player in NBA history to record 10,000 points and 5,000 assists.
He went on to play with Miami, Minnesota, Orlando, Toronto and Houston to end his career. He played in 1,094 games and scored over 14,000 points and had almost 8,000 assists. He averaged 13.2 points and 7.3 assists per game. Strickland is now fully immersed in his job as an assistant coach under John Calipari at UK after serving as director of basketball operations under Calipari at Memphis.
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