5 Biggest Free Agency 'What-Ifs' in Chicago Bulls History

You could come up with numerous "what-if" free agency topics concerning the Chicago Bulls.

For example, what if John Paxson never landed in Chicago? The sharpshooting point guard signed with the Bulls in October 1985. He would eventually hit one of the most memorable shots of all time, which was a championship-winner at the end of Game 6 of the 1993 NBA Finals.       

Paxson's huge three-pointer came with 3.9 seconds remaining in the game, dashing the title hopes of Charles Barkley and the Phoenix Suns. If Paxson misses the shot, the Bulls probably lose that contest and possibly Game 7 as well. 

You never know.

And what if the Bulls didn't hand Eddie Robinson a five-year, $32 million contract in 2001? Well, it would be one less mistake on then-GM Jerry Krause's resume.

5. What If Tracy McGrady Took His Talents to the Windy City?

During the summer of 2000, the Bulls possessed an enormous amount of cap space. It was a great time to have money, as big-time free agents were available like Tim Duncan, Grant Hill and Tracy McGrady.

While Duncan and Hill were pretty much out of the question, the Bulls actually believed they could land McGrady. Unfortunately, the high-flying swingman would say “thanks, but not thanks” and sign a long-term deal with the Orlando Magic.

McGrady would instantly emerge as one of the league’s most dangerous scorers, becoming an All-Star in 2001. With T-Mac headed to Disney World, the Bulls had to settle for the legendary Ron Mercer.

What a consolation prize, right?

The Bulls would struggle mightily over the next few years before finally reaching the playoffs in 2005. If McGrady had wound up in Chicago, it’s likely that the team would’ve experienced success much sooner.

Perhaps Elton Brand wouldn’t have been traded for Tyson Chandler on draft night of 2001 (an awful trade by the way). McGrady could’ve formed a top-notch duo with Brand, who was putting up 20 points and 10 boards a night back in those days.

Throw in guys like Ron Artest and Brad Miller, and the Bulls would’ve been a fun team to watch.

4. What If Jayson Williams Was Picked Up Instead of Dennis Rodman?

Prior to the 1995-96 season, the Bulls acquired Dennis Rodman in a trade that sent Will Perdue to the San Antonio Spurs.

The Bulls simply robbed San Antonio by trading a backup center for a Hall of Famer.

Rodman would team with Michael Jordan and Scottie Pippen to lead Chicago to three consecutive titles (’96-98), as he provided suffocating defense and phenomenal rebounding to the lineup.

“The Worm” was obviously a perfect fit in Chicago. But would Jayson Williams have been as well? A free agent during the summer of 1995, the 6’10" big man was on the Bulls’ wish list. However, he wound up re-signing with the New Jersey Nets and became an All-Star in 1998.

Would the Bulls still have won a trio of titles with Williams on board rather than Rodman? Yes, if Williams would’ve stayed healthy. As a Net, he missed 110 games due to injury during the Bulls’ second three-peat.

Williams wasn’t on Rodman’s level by any means. Yet, he was a great rebounder, as evidenced by a career-high 13.4 average for the 1996-97 season.

3. What If Michael Jordan Left for New York?

The New York Knicks used a chunk of their cap space to sign Allan Houston during the 1996 offseason. While Houston was a quality player, Michael Jordan was the team’s initial target.

After flirting with the Knicks a little bit, Jordan, of course, re-signed with the Bulls and led the team to titles in both ’97 and ’98.

Imagine, though, if MJ actually bolted Chicago for Gotham City. That would be insane, especially since the Bulls and Knicks were involved in an extremely heated rivalry during the ‘90s.

It would sort of be like Derrick Rose leaving the Bulls for the Miami Heat. Ouch, that hurts to think about.

Seeing Jordan and John Starks on the same team would’ve been quite interesting, as those two weren’t exactly best of friends.

Meanwhile, Dream Team teammates Jordan and Patrick Ewing would’ve been an incredible one-two punch. Jordan never played with a superstar center during his entire career. And no, Luc Longley and Bill Wennington don’t count.

It’s basically a guarantee that Ewing wouldn’t be ringless today.

Luckily for Bulls fans, Jordan stayed home and resisted the bright lights of New York City.

2. What If LeBron James and Dwyane Wade Chose Chicago over Miami?

The Bulls' main goal during the 2010 offseason was to land larger-than-life free agent LeBron James. Actually, that was the main goal for several teams across the league. 

As everybody knows, James chose the Miami Heat, joining forces with fellow free-agent signees Dwyane Wade and Chris Bosh, and the Heat have won the last two NBA championships as a result.

Failing to bring King James to town, the Bulls used their cap space to sign Carlos Boozer, Kyle Korver, C.J. Watson and Ronnie Brewer.

Just think if James, along with Wade, headed to Chicago rather than South Beach. A trio of James, Wade and Derrick Rose would be ridiculous to say the least. Three of the league's most unguardable scorers on one team would drive defenders crazy on a nightly basis.

Who would be able to stop this squad? 

With James at small forward, Luol Deng likely would've been traded for a power forward to play alongside Joakim Noah. The addition of James and Wade means Boozer wouldn't have become a Bull. Don't get too upset thinking about that.

Some Bulls fans are still bitter about losing out on James and D-Wade. It sure would've been nice to see those two in Chicago.

1. What If Michael Jordan, Scottie Pippen and Co. Re-Signed?

A slew of Bulls players became free agents following the 1997-98 season.

The list included Michael Jordan, Scottie Pippen, Dennis Rodman, Luc Longley and Steve Kerr. Basically the entire team. 

Sadly, Bulls general manager Jerry Krause didn't want those guys to remain with the team.

His plan was to let them go their separate ways as he attempted to build a new dynasty around younger free agents and high draft picks.   

Jordan would retire, Pippen was dealt to the Houston Rockets (sign-and-trade) and Rodman wasn't brought back. Longley signed with the Phoenix Suns and Kerr wound up heading to the San Antonio Spurs.    

But what if the crew was retained?

Led by Hall of Famers Tim Duncan and David Robinson, the Spurs captured the 1998-99 title. There's no way in the world, though, they would've won it all if Jordan and the gang had stuck around.

Chicago certainly would've beaten San Antonio and joined the Boston Celtics as the only teams in NBA history to win at least four consecutive championships. Even if you're a Spurs fan, you'd have to agree with that statement.  

The Bulls had at least one more championship run left in them. Too bad Krause didn't care.