The Chicago Bulls are one of the most renowned and successful NBA franchises in NBA history, with the greatest player of all time acting as their representative. Michael Jordan led the Bulls to 6 NBA championships and helped make the NBA one of the most popular sports leagues in the world.
The Bulls have had some other great players such as Derrick Rose, Jimmy Butler, and recently Zach LaVine suit up for the team. But Chicago could have also had some more superstar talents play for them, and 5 major names would have altered their history had they committed to the Bulls if not for free agency decisions and trade talks.
5. Dwight Howard - 2012
Dwight Howard would have been a Bull if Chicago would have put together a suitable trade package to convince the Orlando Magic to part ways with their franchise star. A frontcourt with Joakim Noah would have been almost impossible to score against, and Derrick Rose was one of the best players in the game during that time. The fit was there, even if Howard was not keen on becoming a Bull:
As per the Orlando Sentinel, Dwight himself playfully refuted the idea of becoming a Bull:
"Nah, it's pretty cold here," Howard said.
When a reporter responded that Chicago has a mild winter, Dwight Howard said:
"Well, it was cool yesterday. I did get a chance to go out and see the city a little bit. It's a beautiful place. I've been here a couple of times. It's a very nice city."
But Chicago could not get the deal over the line either way, and Howard would eventually become a member of the Los Angeles Lakers. Even if Dwight Howard would struggle with injuries, he was still the best big man in the game and it was not very close. A duo of Howard and Noah would be a mess in today's NBA, but back then, Chicago would have probably been a shoo-in for the Eastern Conference Finals every year.
4. Tracy McGrady- 2000
Rumors were floating around that future All-NBA and All-Star performer Tracy McGrady was interested in becoming a member of the Chicago Bulls. For a chance to have the NBA's leading scorer for the first time since Michael Jordan, Chicago was scrambling for a way to grab an exceptional talent.
As per the Chicago Tribune, T-Mac himself admitted he considered Chicago as much as he did Orlando:
"At this stage of my career, I want to win. I don't want to go backward. I want to move forward and see some improvement. Definitely, Chicago will be one of the teams that I consider ... and Orlando."
McGrady’s agent seemed to convince people otherwise, that the player wants Orlando in the end:
"[The Magic] was the first team he met, and he's from Orlando, so I think that obviously is a factor," Tellem said. "But he has an open mind. He hasn't made up his mind at this point."
Ultimately, McGrady opted for a big deal with the Orlando Magic, where he would blossom into (as expected) the top scorer in the NBA in 2003 and 2004. The Chicago Bulls knew that McGrady was a special offensive player, but never had a shot at signing him to the contract that Orlando offered.
3. Carmelo Anthony - 2014
One of the greatest scorers of his generation, Carmelo Anthony would have played for the Chicago Bulls had he opted to sign a max deal with the Bulls during the 2014 free agency period. After all, Anthony received a ton of interest from the team looking for their next franchise superstar. Chicago might have been the team that Anthony would have ended up with, if not for late doubts from the native New Yorker.
NBC Sports reported that Carmelo Anthony had the Bulls in his sights at one point:
"I was going to Chicago. Derrick Rose, Joakim Noah, I was there, right? I was there," Anthony said. "And then I started getting whispers behind the scenes. Yo, look, this person ain't gonna be there.”
It ain't really right. This and that. It was all of that started to come up in the midst of my decision-making. I wasn't gonna let anything cloud that. I met with New York (Knicks) last.
Like, I think it was the last team I met with because I knew that I was ready to move on from that situation because of what I was dealing with and going through in New York."
But Anthony inked an extension with the New York Knicks, where he would stay until the 2017 season before getting traded to the Oklahoma City Thunder. Anthony averaged 24.7 PPG with the Knicks, so the Bulls missed out on a great opportunity for a box office player that could take over games.
2. Kobe Bryant - 2007
In 2007, the writing was almost on the wall for Kobe and the Lakers. The team was an utter mess without the presence of Shaquille O'Neal, and Kobe Bryant was having to do everything on the court to give the team a chance to win. That is why Kobe Bryant could have continued Michael Jordan's legacy in Chicago.
Bryant was interested in joining Chicago for a host of reasons, but the Bulls could not convince the Lakers to part ways with their global superstar. A deal for Bryant would have to include Luol Deng who Kobe wanted to play with in Chicago. But even the Bulls small forward was not certain how things would play out: "No one is telling me much of anything. I don't know what is going on exactly".
According to ESPN, the Lakers wanted Luol Deng but Kobe Bryant wanted to play with Deng on the Chicago Bulls:
“As ESPN.com reported on Saturday, the Lakers have asked for Deng, Thomas, guard Ben Gordon and rookie Joakim Noah as the core parts of any trade for Bryant.
Contrary to most reports, the Bulls remain ready and willing to deal Deng, the source said. But if they're going to include Deng in a deal, they will not part with more than one of the other three, said the source.
Even then, it is not clear that any trade involving Deng would be acceptable to Bryant, who is wielding the power of the NBA's only no-trade clause by threatening to veto certain deals.
"It's not just the Bulls and Lakers who have to be happy with this deal. Kobe does, too, and that's a major factor," the source said.
The Bulls, according to ESPN.com's source, are willing to offer an alternative package of Gordon, Noah, and Thomas.”
After this trade fell apart, Kobe Bryant would remain a Laker and a Pau Gasol
trade would set the Lakers up for 2 championships just a few years later. Kobe was very close to join Chicago Bulls, but the best for him and the Lakers Nation was that he stayed with the Lakers and won two more championships. And not forget - he beat the Celtics in the NBA Finals in Game 7. That is what every Lakers fan wanted to see.
1. LeBron James - 2010
Chicago had their best chance at replacing Michael Jordan when LeBron James was a free agent in 2010. The King had a long free agency period where he was considering a host of teams including the Knicks, Nets, Cavaliers, Heat, Clippers, and Bulls.
Chicago, specifically, was hell-bent on having LeBron join Derrick Rose in Chicago with the likes of Chris Bosh also playing a role. After all, the superstars were almost all-in with Chicago as their destination.
Dwyane Wade admitted Chicago was a reasonable choice in free agency after multiple visits:
“I mean, this was a place I wanted to play. It was a place that LeBron also loved. We loved the city of Chicago. It’s a great market, as well.
Obviously, the sunny sun of Miami is great, too. We had two great choices."
LeBron, Rose, and Bosh would have brought championships back to Chicago but instead, The King famously opted for Miami. The Bulls will forever rue the chance to have LeBron because 4 straight NBA Finals with the Heat was an indication of what The King would have done in Chicago with Derrick Rose.