McGrady really began to show off his versatility during the 1999-2000 season, his third, when his athletic drives to the basketball and his hawking defense helped the Raptors led by his cousin, Vince Carter reach the NBA playoffs for the first time. McGrady, nicknamed T-Mac, became a free agent after the playoffs and agreed to a seven-year, $92.7 million sign-and-trade deal with the Orlando Magic on Aug. 3, 2000 to pair with Grant Hill and try to build a championship team. McGrady went from averaging 15.4 points per game his final season in Toronto to claim a regular spot among the league's top scorers while playing for Orlando and lead the Magic to the playoffs all but his final year with the team. He also won two NBA scoring titles in Orlando during the 2002-03 (32.4 points per game) and 2003-04 (28 ppg) seasons. McGrady holds Orlando's single-game scoring record after racking up 62 points against the Washington Wizards on March 10, 2004, one of his final games with the Magic.
By the summer of 2004, McGrady had become frustrated with trying to carry the Magic as their captain and leading scorer and Hill mostly out with injuries since the two players had joined the team. McGrady told Magic General Manager John Weisbrod that he could not promise he would sign an extension with Orlando when he was able to opt out of his contract in July 2005, and he was traded to the Rockets along with Juwan Howard, Tyronn Lue and Reece Gaines for Steve Francis, Cuttino Mobley and Kelvin Cato on June 29, 2004. McGrady signed an extension with Houston that summer, is captain of the Rockets and he and Chinese star Yao Ming now form the foundation of the Rockets' playoff teams.
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