5 Worst Decisions of Jerry Reinsdorf's Chicago Bulls Era

Although the Chicago Bulls have won six NBA championships with Jerry Reinsdorf as the owner, the team has made plenty of bad decisions during his tenure.  

Reinsdorf has been the boss since 1985, one year after Michael Jordan took his talents to the Windy City. A trio of general managers have been employed by the Bulls since ’85—Jerry Krause, John Paxson and Gar Forman.

All three men have made wise decisions, but they’ve also made choices that leave fans scratching their heads. While Reinsdorf doesn’t come up with every idea, he has the final say.

One decision that didn’t make the list is the hiring of Tim Floyd, who compiled a horrific 49-190 record as head coach of the Bulls. Any coach would’ve failed with the expansion-caliber rosters the Bulls possessed in the late ‘90s and early 2000s.  

5. Signing Ben Wallace

During the summer of 2006, the Bulls signed Ben Wallace to a four-year deal worth $60 million.

It looked like a good move for the Bulls at the time. As a member of the Detroit Pistons, Wallace had been named Defensive Player of the Year a whopping four times and helped the team capture a title in 2004.

Unfortunately, the Chi-Town version of Big Ben just wasn’t the same as the Motown version. Wallace averaged only 5.8 points and 9.8 rebounds per game in his 127 games as a Bull. He was dealt to the Cleveland Cavaliers in 2008.      

The Bulls have made a few bad free-agent signings over the years, and this is the perfect example.  

4. The Eddy Curry-Tyson Chandler Experiment

Two high school big men, Eddy Curry and Tyson Chandler, were acquired by the Bulls via the 2001 draft. The team drafted Curry fourth overall and traded Elton Brand to the Los Angeles Clippers for Chandler, the No. 2 overall pick.

Both teenagers possessed an enormous amount of potential. Curry was nicknamed “Baby Shaq,” while Chandler was supposed to be Kevin Garnett 2.0.

Bulls fans know how the story goes, though.  Let’s just say neither player would have a spectacular career in Chicago.  

By choosing Curry, the Bulls passed up several future All-Stars in the ’01 draft class, such as Tony Parker, Zach Randolph, Gilbert Arenas and Joe Johnson. And by shipping Brand out of town, the team lost a perennial 20-10 guy who became an All-Star in sunny Los Angeles.

 The Curry-Chandler experiment was basically a waste of time.    

3. Trading Ron Artest and Brad Miller for Jalen Rose

In 2002, the Bulls traded Ron Artest (now known as Metta World Peace, of course), Brad Miller, Ron Mercer and Kevin Ollie to the Indiana Pacers for Jalen Rose, Travis Best, Norman Richardson and a second-round draft pick.    

What an awful trade for the Bulls.

Rose was decent during his tenure in Chicago, but Artest and Miller would go on to become high-impact players.

Artest blossomed into an All-Star and a lockdown defender, as he was named Defensive Player of the Year in 2004. And Miller emerged as a two-time All-Star and one of the better passing big men in the league.

2. Trading LaMarcus Aldridge

The Bulls made a brilliant move in 2006 by drafting Texas big man LaMarcus Aldridge second overall. 

However, the team would immediately make a not-so-brilliant move by trading Aldridge to the Portland Trail Blazers for LSU’s Tyrus Thomas, who was the fourth overall pick.   

Thomas went on to be a major disappointment, averaging just 7.9 points and 5.3 rebounds per game during his short career in Chicago. And meanwhile, Aldridge, a two-time NBA All-Star, is one of the top power forwards in the game today.     

The Bulls have been looking for a star to pair with megastar Derrick Rose, and Aldridge could’ve have been that guy. But then again, if he had stayed in Chicago, it’s possible the Bulls never would’ve landed the top pick in ’08 to draft Rose.

1. Dismantling the Dynasty

The San Antonio Spurs won it all in 1999. That had to be hard for Chicago sports fans to see.

Why? Because the Bulls should’ve won that title, which would’ve been their fourth straight and seventh in nine years.

Jerry Reinsdorf and Jerry Krause broke up the dynasty a year too early, basically showing the likes of Michael Jordan, Phil Jackson and Scottie Pippen the door.

Jordan retired, Jackson left and Pippen was sent to the Houston Rockets in a sign-and-trade deal. Dennis Rodman wasn’t re-signed and fellow free agents like Steve Kerr and Luc Longley took their talents elsewhere.

The Jerrys wanted to build a new dynasty through free agency as well as the draft. Their rebuilding plan would backfire dramatically, though, as major free agents spurned the Bulls, and many of the draft picks were disappointments.    

Jordan and Co. should’ve been given just one more year to win championship No. 7. This is easily the worst decision in Bulls history.