In 2003, Riley stepped down as head coach to focus on his front office duties, handing the coaching reins to his longtime assistant Stan Van Gundy. This period saw Riley the executive shine, as he made a series of moves that would set the stage for future success. Most notably, he drafted Dwyane Wade in 2003, a decision that would alter the course of the franchise.

Riley returned to the bench in December 2005, replacing Van Gundy as head coach. The following year, he engineered one of the most significant trades in NBA history, acquiring Shaquille O'Neal from the Lakers. This move, combined with the emergence of Wade as a superstar, propelled the Heat to the 2006 NBA Championship, the first in franchise history.