Grant was drafted by the Chicago Bulls with the 10th overall pick of the 1987 NBA draft. The 6 ft 10 in (2.08 m) tall power forward / center teamed with fellow draft-day acquisition Scottie Pippen to form the Bulls' forward tandem of the future, although he initially backed up incumbent Charles Oakley, one of the league's premier rebounders and post defenders.
In 1988, Grant moved into the starting lineup when Oakley was traded to the New York Knicks for center Bill Cartwright. He immediately became the Bulls' main rebounder, and established himself as the Bulls' third scoring option after Michael Jordan and Pippen, forming one of the league's best trios. Grant was noted for his defensive play; he was selected four times for the NBA All-Defensive Team.[3] He helped Chicago win three consecutive NBA championships (1991, 1992, and 1993), securing the third with a last-second block on Kevin Johnson.
Grant, who was diagnosed with myopia and wore eyeglasses, began wearing goggles fitted with prescription lenses on the court starting with the 1990–91 season.[4] The goggles soon became a trademark for Grant. Although he eventually received LASIK surgery to correct his sight, he continued to wear the goggles on the court after he had heard from parents that he had become an inspirational figure to children who wore eyeglasses.[5]
After Jordan's first retirement following the 1992–93 season, Grant became the number-two star behind Pippen, and helped the Bulls push the Knicks to seven games in the second-round playoff series before being eliminated. Grant played in the 1994 NBA All-Star Game, posting four points and eight rebounds in 17 minutes. During the 1993–94 season he recorded career-best averages in scoring (15.1), rebounding (11.0), and assists (3.4).