Scott Boras has represented Holliday as his agent since he turned professional. Holliday described his relationship with Boras and his staff in that he "enjoy(s) sitting down and talking to them. Scott is as accessible as you want him to be. I could call him right now. He's got a lot of clients and people say they don’t hear from Scott but he’ll give you as much or as little attention as you want." Holliday further explained that due to the amenities the Boras Corporation provides, including a staff psychologist, research to assist players in prolonging careers, studies into arbitration cases, and statistical performance computation, he felt that Boras' agency gave him the best opportunities to succeed.