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Klein played four years of college soccer at Indiana University, from 1994 to 1997. In total, he started 88 games for the Hoosiers, registering 11 goals and 11 assists as a senior.
Upon his graduation, Klein was selected fourth overall by the Wizards in the 1998 MLS College Draft. He received little playing time as a rookie, starting eight games and substituting into nine, and scored no points. Starting in 1999, however, Klein began to cement a place for himself as one of the league's best midfielders; in the 1999 season, Klein started 24 games for the Wizards, registering six goals and five assists. He started 26 games in 2000, scoring six goals and eight assists, while help lead the Wizards to an MLS Cup victory. Klein has been an equally important part of the Wizards midfield for the last four years, although his 2004 campaign was cut short by a torn ACL.
Klein has been a fringe player for the United States national team for the last several years. He received his first cap October 25, 2000 against Mexico, his debut for the men's national team at any age level. He has played in a total of 16 games for the national team, scoring three goals; his best year was 2003, when he played in seven games, and scored all three of his goals.