Chicago Bulls: 10 Biggest "What Ifs" in the Team's History

There are millions of things that could have happened in Chicago Bulls history.

What if Tim Duncan had taken his talents to Chicago as a free agent in 2000?

What if the Bulls had kept LaMarcus Aldridge instead of trading him to Portland for Tyrus Thomas on draft night 2006?

What if both LeBron James and Dwyane Wade had signed with the Bulls last summer instead of teaming it up down in Miami? 

Here's a look a the 10 biggest "what ifs" associated with Chicago's famous basketball franchise.    

Enjoy.

10. What If Jay Williams Never Wrecked His Motorcycle?

Chicago took exciting Duke point guard Jay Williams with the second overall pick in the 2002 NBA draft.

He would go on to have a decent, but definitely not legendary, rookie season in Chicago, averaging 9.5 points and 4.7 assists per game.

But although he was a bit of a disappointment during his first year in the league, several fans and experts believed Williams was going to eventually turn into a franchise point guard for the Bulls, similar to what Derrick Rose is for the team today.  

Unfortunately, though, J-Will would crash his motorcycle in the offseason following his rookie season and never played another minute in a regular-season NBA game.   

If he didn't have that career-ending accident, there's a chance he would still be in Chicago right now running the point and Rose would be starring in some other town. 

9. What If the Bulls Had Traded for Kobe Bryant?

Many fans can't stand Kobe Bryant because they think he's a Jordan copycat.

A few years back, Bryant wasn't happy as a Laker and supposedly wanted to be traded to the Bulls.

The trade obviously never happened, and he remained in Los Angeles, where he will more than likely finish his career.

But if the trade did go down, fans would hate Mr. Bryant even more, believing he wanted to play in Chicago just so he could be in the same place that Jordan spent most of playing days.

With Kobe as a Bull, the team wouldn't have been bad enough to land a high enough pick to draft Derrick Rose.      

8. What If the Bulls Had Drafted Karl Malone?

The Bulls made a nice move in the 1985 draft by trading the 11th overall pick, Keith Lee, to Cleveland for Charles Oakley.

But a much nicer move would have been to draft Karl Malone, who ended up falling to the Utah Jazz 13th overall.

Malone never managed to win a championship during his outstanding 19-year career. But if he had landed in Chicago and teamed with Jordan, he most likely would have picked up several rings.

7. What If Jayson Williams Was Brought in Instead of Dennis Rodman?

Chicago captured six titles mostly due to Michael Jordan's scoring, Scottie Pippen's defense and Phil Jackson's coaching. But three of those titles wouldn't have been won without Dennis Rodman's rebounding.

Rodman was acquired by the Bulls prior to the 1995-96 season in a trade that sent Will Perdue to the San Antonio Spurs.

Rodman fit in nicely at power forward in Chicago, replacing Horace Grant, who had left for Orlando the previous year.

However, New Jersey Nets free agent Jayson Williams was the Bulls' first choice to fill the spot and not Rodman.

Williams would end up re-signing with the Nets and passing up the chance to win titles with Jordan, Pippen and Co.

If he had decided to go to Chicago, would he have helped the Bulls win three straight titles like Rodman did? Probably not. Williams was a superb rebounder, but he isn't one of the top defenders in NBA history like Rodman is.

6. What If Michael Beasley Was Drafted Instead of Derrick Rose?

The Bulls lucked out by winning the No. 1 pick in the 2008 draft.

After thinking about taking Kansas State forward Michael Beasley, the team decided to go with Memphis point guard and Chicago native Derrick Rose.

Beasley ended up being selected by the Miami Heat second overall and would struggle in his two years in South Beach.

He put up good numbers this past season in Minnesota, but he's not on the same planet as Rose, who as named the 2011 NBA MVP.      

What if the Bulls had passed up Rose and selected Beasley with that top pick? Let's just say they wouldn't be one of the league's most popular teams right now.  

5. What If Magic Johnson Had Made His Way to Chicago?

Earvin "Magic" Johnson spent his entire 13-year career with the Lakers, leading the team to five titles in the 1980s.

However, the Hall of Fame floor general came close to landing in Chicago instead of Los Angeles. In 1979, the Bulls and Lakers participated in a coin flip to determine who would win the top pick in that year's draft.

The Lakers obviously won and chose Johnson, who later became the greatest point guard in the history of basketball, and the Bulls had to settle for the second overall pick, which they used on David Greenwood.

Greenwood never did much for the Bulls, but imagine what Johnson would have done if the team had won the top pick and drafted him.

Johnson probably wouldn't have won five titles in Chicago like he did in L.A. But you never now, maybe the Bulls have an awful 1983-84 season and still end up drafting Michael Jordan. A Jordan-Magic backcourt would have been ridiculous.

4. What If Scottie Pippen Was Traded for Shawn Kemp?

Scottie Pippen was on the trading block during Michael Jordan's first retirement in 1994. There was a rumor out there that had Pip heading to the Seattle SuperSonics in a deal for All-Star forward Shawn Kemp. 

The trade never went through. Pippen stayed in Chicago and eventually helped the Bulls continue their memorable dynasty of the '90s. And Kemp continued to be one of the game's top players for a few more seasons before becoming an overweight bench player.   

But what if the trade did go through? Would Jordan, who later returned to Chicago, have helped Kemp keep his head on straight? Would Kemp have helped the Pippen-less Bulls win multiple titles? 

3. What If the Dynasty Wasn't Dismantled Too Early?

The Bulls dynasty came to an end following the team's sixth and final championship in 1998.

Jordan retired for the second time, Pippen was traded to Houston, Phil Jackson left, Rodman didn't re-sign and pretty much everybody departed the city of Chicago.

Bulls owner Jerry Reinsdorf and GM Jerry Krause had a plan to rebuild around sought-after free agents and high lottery picks.

The plan failed miserably, as the Bulls went from the league's most respected team to basically a joke.

If the Jerrys had kept that squad together at least one more year, they would have had a great chance to add a seventh title by beating San Antonio in 1999. 

2. What If Michael Jordan Didn't Retire in 1993?

In October 1993, Michael Jordan retired form the league just four months after leading the Bulls to their third NBA title.

Following the brief retirement, he returned to the Bulls in March 1995. With MJ back in the picture, Chicago went on to win three more titles from 1996-1998.

If Jordan didn't leave basketball in '93 and continued to play, there's a good chance that the Bulls would have tied the old Boston Celtics record of eight straight titles.   

The Hakeem Olajuwon-led Houston Rockets, who won back-to-back titles during Jordan's absence were good, but let's face it, they wouldn't have been good enough to knock off the Bulls in the NBA Finals.     

1. What If Michael Jordan Wasn't Available to Draft?

As most NBA fans know, the Bulls selected Michael Jordan with the third overall pick in the 1984 draft.

And everybody also knows that Jordan could have been drafted second overall by the Portland Trail Blazers.

If Jordan had went to Portland, he and Clyde Drexler would have formed a nice one-two punch that probably would have led the Blazers to a slew of titles.

So what would that have meant for the Bulls?

After drafting Sam Bowie, one of the biggest busts in sports history, the team wouldn't have had a dynasty and might have became the Los Angeles Clippers of the East.