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Early career

DeMerit was a three-sport high school athlete in Wisconsin, where he participated in basketball and track in addition to soccer. He attended Bay Port High School and graduated in 1998.

DeMerit played college soccer at the University of Illinois at Chicago, where he moved from playing forward to defender. While in college, DeMerit formed part of a defensive backline that helped lead the team into the NCAA playoffs in 2000.

Although he played with Chicago Fire Premier, the development team of the Chicago Fire in the USL Premier Development League, he was not drafted or signed by any Major League Soccer clubs following graduation from college. After spending some time working as a bartender, DeMerit took the advice of a former European teammate and decided to take advantage of his European Union work status (due to his Danish grandfather) by moving to England in 2003 with only $1,800, in an attempt to find a club to play for.
He started off playing in the ninth tier of English soccer for Southall, earning only £40 a week.

In July 2004, DeMerit joined Northwood, a seventh-tier side, to play in some of their pre-season matches. Northwood played Watford, then a Football League Championship team, in their second pre-season match. During the course of the match, DeMerit impressed then Watford manager Ray Lewington enough to earn a two-week trial. Following the trial, DeMerit signed a one-year contract with Watford to play in their 2004–05 season.

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