McGrady plays either shooting guard or small forward, and is also one of the first players who went from high school (Mt. Zion Christian Academy) straight to the NBA without attending college (from the mid-90's high school exodus). He created national buzz after his performance in adidas ABCD Camp, which is for the best high school players in the nation. He was drafted ninth in the first round of the 1997 NBA Draft by the Toronto Raptors. Chicago Bulls GM Jerry Krause had arranged a draft-day trade to send Scottie Pippen to Toronto for the 4th overall pick, which he would have used to take McGrady. But, Krause was forced to call off the deal when Michael Jordan threatened to retire if it was made. McGrady improved his numbers in all statistical categories in each year. The teammate and cousin (by marriage) of Vince Carter, McGrady often found himself in Carter's shadow, whose dunks made him an instant star. McGrady even assisted Carter in the 2000 NBA Slam Dunk Contest, an event in which McGrady also was competing. While Carter was responsible for scoring, it was McGrady's job to be the team's defensive stopper and ball distributer. He recognized that McGrady was very versatile, and that he would demand great attention during the offseason. The young duo of Carter and McGrady led the Raptors to their first playoff berth in the 2000 Playoffs, but they were swept by the New York Knicks in 3 games.

McGrady's career took off when he forced a sign-and-trade to the Orlando Magic in exchange for a first round draft pick in 2000. In the 2000-2001 season, he won the NBA Most Improved Player Award and was selected a starter in the All-Star Game. He and Grant Hill both were supposed to be valuable players for Orlando, but because of a long series of injuries to Hill, McGrady became the top player for the Magic. In the 2002-2003 season, McGrady captured the NBA scoring title, averaging 32.1 points per game. In the 2003-2004 season, he once again captured the NBA scoring title, averaging 28 points per game and set an NBA season high when he dropped 62 against the Washington Wizards on March 10, 2004. With this performance, he became only the 4th player in the past 12 years to score over 60 points in a game. McGrady was ranked #75 on SLAM Magazine's Top 75 NBA Players of all time in 2003. However, fortunes turned for the worse in Orlando after a league-worst 21 win season. Amid allegations of slacking off during games (he later admitted to not giving 100% every game that season), the relationship between McGrady and Magic General Manager John Weisbrod worsened. Soon, Weisbrod decided to trade the unhappy McGrady instead of keeping him for another year and risk him leaving the Magic without compensation.