Riley's early years in Miami were marked by a rapid transformation of the Heat roster. He orchestrated trades to bring in players like Alonzo Mourning and Tim Hardaway, quickly turning the Heat into a playoff contender. The team adopted Riley's trademark physical, defensive-minded style, becoming one of the toughest outs in the Eastern Conference.
Under Riley's guidance, the Heat made the playoffs in each of his first five seasons as coach, including a trip to the Eastern Conference Finals in 1997. However, despite regular-season success, a championship remained elusive.