As a free agent in 2003, Holliday received interest from multiple teams including the Arizona Cardinals and the Seattle Seahawks. However, it was the Kansas City Chiefs that landed him on April 7, inking him to a five-year deal worth $21.3 million and a signing bonus of $4 million. That being the case, the structure of the contract created what essentially would be a two-year deal due to a $5 million bonus owed before the third year. As things would turn out, those first two years would be the length of Holliday's tenure in Kansas City.