The franchise had recently been rebuilt led by head coach Pat Riley and featured all-stars Alonzo Mourning, Tim Hardaway and another shooting guard who would split minutes with Lenard, Dan Majerle.

In the 1999–2000 season Lenard played mostly off the bench, but averaged double-figure scoring with 11.9 points a game while shooting 39 percent from three-point range.

Injuries would keep him out of the tail end of the season as well as the playoffs in which the Heat defeated the Detroit Pistons before once again falling to New York in a seven-game series.

In his first season with the Nuggets, Lenard started in 58 of 80 regular-season games and averaged 12.2 points for a team that failed to make the playoffs, but he placed 10th in the league in total three-point field goals made.

The Raptors had made the playoffs for three straight seasons and featured superstar Vince Carter, all-star Antonio Davis and coach Lenny Wilkens.

The Nuggets had continued their playoff drought, but had managed to secure the 3rd pick in the 2003 NBA draft and selected college star and NCAA Champion Carmelo Anthony.

Lenard was also the winner of the 2004 NBA All-Star Weekend Three-point Shootout which took place in Los Angeles, and would see his first postseason action since 1999, averaging a personal best 17 points a game in a five-game series loss against the top-seeded Minnesota Timberwolves.