The Chicago Bulls spent years chasing a very specific kind of future, and for a long time that future had a name: Tracy McGrady.
Back in 1997, general manager Jerry Krause tried to swing a deal with Toronto that would have sent Scottie Pippen to the Raptors in exchange for McGrady’s rights. Owner Jerry Reinsdorf shut that down.
Three years later, when McGrady hit free agency, Chicago made another push. This time, McGrady chose Orlando and stayed closer to home in Florida.
Krause’s fixation made sense. McGrady went on to become a seven-time All-Star and a two-time scoring champion, and the Bulls were left to imagine what the 2000s might have looked like if they had built around him.
Now Bill Simmons says Chicago may have finally found the player it spent nearly three decades looking for. In his view, fourth overall pick Caleb Wilson looks like McGrady’s doppelganger.
“The craziest part is that Tracy McGrady underachieved.”
That’s Simmons’ take, and it comes with the kind of context only a Hall of Fame-level career can provide. McGrady was one of the great scorers of his era, but injuries kept cutting into his best years.
He played fewer than 60 games in five of his 15 professional seasons, and many of those absences came during his peak. Simmons suggested that if McGrady had stayed healthy, multiple MVPs could have been in play, and maybe Orlando or Houston would have won a championship.
The reason the Bulls are paying attention is that Simmons has already seen enough from Wilson to get genuinely fired up. He has been especially impressed by what he’s seen in Summer League, where Wilson has shown the kind of explosiveness that brings McGrady to mind. Simmons also believes Wilson’s shooting looks more advanced than draft experts expected.
There’s even a statistical benchmark floating in the background. McGrady averaged 15 points, 6 rebounds, and 3 assists in his first season as a starter. If Wilson can get to those numbers, it would only strengthen the comparison.
Simmons does not hand out that kind of praise lightly. He’s watched basketball his entire life, and when he gets animated about a young player, it usually means something. By his own standard, Wilson has been the most exciting prospect he’s talked about in years.
That leaves the Bulls with the kind of question they’ve been asking since the McGrady chase began: can they turn the talent into something bigger? McGrady’s career was brilliant, but he never landed on a roster built enough around him to win it all.
Toronto moved on before Vince Carter fully took off. Orlando paired him with Grant Hill before injuries changed everything.
Houston had McGrady alongside Yao Ming, but health kept getting in the way, and heavyweights like San Antonio and Los Angeles kept standing in the path.
If Wilson really is the player Simmons thinks he is, Chicago may have found its franchise cornerstone at last. The next step is the one that always mattered most with McGrady: building the right team around him.
In Other News...
Matas Buzelis Just Picked An Unexpected Blueprint For His Next Leap
Matas Buzelis has already given the Bulls a real reason to be encouraged in his second NBA season, turning a promising rookie profile into something much more productive across 77 games. The 2024 draftee has shown clear growth as a scorer and defender, and now his offseason attention is shifting toward the kind of physical development that can help him hold up when the game gets tighter and bodies get bigger.
On the Ball in the Family podcast, Buzelis said he wants to attack the rim more and believes he leaned on too many threes this season, which is a useful self-scout for a young wing trying to round out his game. He also laid out a workout plan that includes time with Deni Avdija, Franz Wagner and Kevin Durant, a mix that says plenty about the kind of two-way, downhill player he wants to become as he looks to get stronger and more efficient. [Read more 🡒]
Celtics Just Delivered Another Brutal Reminder Of The Bulls Draft Problem
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For Chicago, the sting is obvious because Julian Phillips went three picks earlier in that same draft, and the Bulls no longer have him in the picture. It fits a broader pattern that has dogged the front office, with recent draft decisions and trades failing to produce enough long-term answers, leaving the team once again watching another organization turn a second-round swing into something more stable. [Read more 🡒]
Bulls Fans Should Be Watching OKC For A Frontcourt Opening
The Thunders latest three-team deal was less about adding a headline name than about keeping the books clean, as Oklahoma City moved Lu Dort to Atlanta, Zaccharie Risacher to Dallas and Ryan Nembhard to the Hawks while bringing back three second-round picks. For a team operating with the NBAs second apron in mind, that kind of move fits the broader pattern: trim a little here, preserve flexibility there, and keep the roster nimble enough to handle the next round of decisions.
For Bulls fans, the reason to keep one eye on Oklahoma City is the frontcourt. Jaylin Williams is part of the long-term picture there for now, but the Thunders willingness to make cap-driven choices around useful rotation pieces is exactly the sort of dynamic Chicago should monitor, especially with a versatile big on a manageable timeline and a skill set that would make sense in plenty of places if the roster math ever shifts. [Read more 🡒]