In the 1983 NBA draft Drexler was selected by the Portland Trail Blazers with the 14th overall pick. He averaged 7.7 points in 17.2 minutes per game in his rookie season. His second season was his breakout season, in which he averaged 17.2 points, 6 rebounds, 5.5 assists and 2.2 steals per game. In his third season, Drexler made his first All-Star team while averaging 18.5 points, 5.6 rebounds, 8 assists and 2.6 steals. In the 1989–1990 season, Drexler led the Portland Trail Blazers to the NBA Finals, averaging 26.4 points and 7.8 rebounds, but his team lost to the Detroit Pistons in five games. In the 1990–1991 season Drexler led Portland to a franchise-best 63–19 record. Heavily favored to win the West, the Los Angeles Lakers upset the Trail Blazers by winning the Western Conference Finals.