More than a decade ago, the Bulls were in hot pursuit during free agency of one of the brightest young talents in the NBA, 20-year-old Tracy McGrady. The Bulls, of course, came away empty-handed in trying to reel in the 6-foot-8 small forward, but how might their future and McGrady's have changed had he decided to take his talents to the Windy City?
McGrady, who retired Monday after an outstanding yet injury-riddled 15-year NBA career, had averaged 11 points on 45 percent shooting in three years with the Raptors, but after coming out of high school and being selected ninth overall in the 1997 NBA Draft, it was apparent his future was bright after leading Toronto -- along with a healthy, in-his-prime Vince Carter -- to the playoffs for the first time in franchise history, averaging 15.4 points and 6.3 rebounds.
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But T-Mac wasn't alone in the heralded 2000 free-agency class. Two other superstars -- San Antonio's Tim Duncan and Detroit's Grant Hill -- were also seeking maximum contracts and had plenty of interest from teams around the league.
The most active team that summer was the Orlando Magic, who had scrapped their way to a 41-41 record and, after closing out the season 10-5, missed out on the No. 8 seed in the East by one game to the 42-40 Milwaukee Bucks. With 31-year-old Darrell Armstrong and 32-year-old Chris Gatling not getting any younger, and 23-year-old Ron Mercer set to become a free agent, the Magic were ready to take the next step in their rebuilding process. The prior year general manager John Gabriel had gutted the roster, trading away Penny Hardaway, Nick Anderson, Horace Grant and Ike Austin, freeing up cap space with the free agency class of 2000 in mind.
Gabriel's first goal was to lure Duncan and Hill to Orlando. Duncan had averaged 22 points and 12 rebounds in three seasons with the Spurs, including an NBA championship, two All-Star appearances and an NBA Finals MVP. Hill had exploded with the Pistons, averaging 21.6 points, 7.9 rebounds and 6.3 assists in six seasons with the Pistons. Believe it or not, Hill had missed just 25 games through those six seasons and, entering his prime at 27, appeared on his way to becoming one of the game's all-time greats.
Duncan wound up staying in San Antonio, while Hill, looking for change after failing to advance the Pistons out of the first round despite plenty of regular season success, agreed to a deal with the Magic. Gabriel had his first max player in hand, and now he needed a second.
That left McGrady, who showed interest the Bulls while also considering the prospect of playing closer to his hometown of Auburndale, Fla., less than an hour from Orlando and four hours from Miami.
In the first two seasons of the post-Jordan era, the Bulls had gone 30-102 and, outside of reigning Rookie of the Year Elton Brand, showed little promise in improving from their 17-65 record in 1999-2000.
The Chicago Tribune reported that summer the Bulls pulled out all the stops for McGrady when he visited, with Benny the Bull and the Luvabulls greeting him at the airport, a small band playing "Sweet Home Chicago," going to dinner with Jerry Krause and Brand, and throwing out the first pitch at a Cubs-White Sox game. Still, reports indicated that McGrady's stop in the Windy City was simply a "courtesy visit," as he had his mind set on playing closer to home and competing for a championship with either the Magic or Miami Heat.
Days before his visit to Chicago, Hill had pledged his commitment to Orlando. One week after his extravagant visit to Chicago, McGrady decided to team up with Hill, Doc Rivers and the young Magic. On Aug. 3, both Hill and McGrady signed seven-year, $92.8 million contracts as part of sign-and-trades with the Pistons and Raptors, respectively. (Interesting note: the Magic sent Ben Wallace to the Pistons in the sign-and-trade; four years later Wallace was the defensive player of the year and leading the Pistons to an NBA title)
In the three seasons the pair of max-contract forwards played together -- Hill missed the entire 2003-2004 season, and McGrady was dealt to Houston after that season -- the Magic finished with 43, 44 and 42 wins, respectively, and lost in the first round of the playoffs each year. McGrady went on a tear in his time in Orlando, averaging 28.1 points, 7.0 rebounds and 5.2 assists. He led the NBA in scoring twice, was an All-Star all four seasons and his 2002-03 season is one of the best single-season performances in NBA history. Hill dealt with multiple ankle injuries and never became the player the Magic had hoped for, playing in just 200 of a possible 492 regular-season games in six years.
For the Bulls, missing out on McGrady meant going with back-up free agent options in Ron Mercer and Brad Miller, resulting in a 15-67 record, still the lowest win percentage in franchise history. Until the youth infusion of Luol Deng, Ben Gordon and Kirk Hinrich led the Bulls back to the playoffs in 2004-05, watching McGrady dominate the league while single-handedly carrying the Magic to the playoffs was difficult. Whether he was seriously considering Chicago when free agency began that year, the "what-ifs" are endless, as McGrady would have had the chance to team up with Brand -- who was traded the next season -- and perhaps form a young core capable of competing for an NBA championship.