3. Tracy McGrady
Year: 2000
Team he ended up with: Orlando Magic
The Magic appear twice on this list in a big way with their entanglements in the trade and free agent markets with the Chicago Bulls. There were two opportunities for the Bulls to get involved with the Magic and further their chances to win the franchise’s first NBA Championship since the Jordan-era ended.
The first spot on the list with the Magic was when Howard was dealt to the Lakers in 2012. The other spot for the Magic here goes way back to the turn of the century in the summer of 2000. A transcendent superstar in the NBA throughout the late 1990’s and early-to-mid 2000’s is the Hall-of-Fame wing Tracy McGrady.
A seven-time All-NBA selection and two-time NBA Scoring Champion, McGrady was one of the most exciting and polarizing players to watch during his time with the Toronto Raptors and the Magic. His peak finally topped out in the mid-to-late 2000’s when he played with the Rockets and fellow Hall-of-Famer Yao Ming.
It wasn’t too long until T-Mac registered 51 points in 2003 against the Bulls. That Magic team was building toward the most relevance it would see this century between McGrady and Howard making runs to the playoffs in the East. T-Mac passed up his opportunity to play for the Bulls in 2000 for a big deal with the Magic. But an old Chicago Tribune report shows he was interested in coming to the Windy City at one point.