In 1989, he 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 Jordan and Pippen, forming the one of league's best trios. He helped the Bulls win three consecutive world championships (1990-91, 91-92, and 92-93), and after Jordan retired following the 1992-93 season, he became the number two star behind Pippen, and helped the Bulls push the Knicks to seven games in the second-round playoff series. In the offseason however, he left the Bulls as a free agent, joining the young and rising Orlando Magic, led by Shaquille O'Neal. Grant helped the Magic reach the 1994-95 NBA Finals, where they were swept in four straight games. Grant spent the next several seasons with the Magic, until he joined the Seattle Supersonics in 1999. After the 1999-2000 season, he was involved in a three-way trade in which Glen Rice of the Los Angeles Lakers was sent to New York, Patrick Ewing of the Knicks was sent to Seattle, and Grant went to the defending champion Lakers. He helped them win the championship in 2000-2001, and in the offseason signed back with the Magic. He retired in the beginning of the 2002-2003 season, but came back and signed with the Lakers in the summer of 2003.
Grant is known as a strong defender and rebounder who can also provide a consistent source of points.