Michael Jordan, Scottie Pippen and Phil Jackson made the Chicago Bulls a hallmark organization by leading the franchise to six championships during the 1990s.
However, since the Jordan era ended, the Bulls have had only one superstar play for the team. That was Chicago's own Derrick Rose, who won the 2011 MVP award — becoming the youngest MVP in NBA history at the age of 22.
The Bulls got lucky by landing Rose in the 2008 draft, though, not via free agency. Chicago magically won the draft lottery and took Rose over Michael Beasley.
During the summer of 2010, the Bulls pursued stars LeBron James, Dwyane Wade and Chris Bosh in free agency, striking out with all three and ending up with Carlos Boozer as their consolation prize.
While it was no doubt fun watching Rose win the MVP award, it would have been better if the Bulls could have gotten another superstar next to Rose so Chicago could have possibly won a title.
The Bulls have a history of not doing well in free agency. For this piece, we ranked Chicago's five worst free-agent signings of all time.
5. Tomas Satoranksy
The Bulls signed Satoransky to a three-year, $30 million deal as a free agent in the summer of 2019. Before the 2019-20 season was suspended, Tomas was averaging 9.9 points, 3.9 rebounds and 5.4 assists for the team.
Chicago was paying Satoransky $10 million for the season. The Bulls could have got Rose for a lot cheaper instead but they chose not to bring the former MVP back home even though Rose was interested in coming back.
Rose averaged 18.1 points and 5.6 assists for the Detroit Pistons prior to play being suspended due to COVID-19. He was making $7,317,073.
The Bulls are paying Satoransky more than Rose and getting way less production.
4. Thaddeus Young
The Bulls had a bad 2019 free agency period. The team overpaid to get Young, giving the lefty a three-year, $41 million contract.
Young averaged 12.6 points, 6.5 rebounds and 2.5 assists in 2018-19 with the Indiana Pacers and the Bulls didn't really need his services since they had Lauri Markkanen.
Before the 2019-20 season got suspended, Young appeared in 64 games for the Bulls. He was putting up 10.3 points, 4.9 rebounds and 1.8 assists. Young is set to make $13,545,000 next season and then $14,190,000 in 2021-22, though only $6 million of that is guaranteed.
Young was supposedly unhappy with his role and minutes under Bulls head coach Jim Boylen for most of the season. Don't be surprised if new Chicago president of basketball operations Arturas Karnisovas tries to move Young whenever the 2020-21 offseason begins.
3. Ben Wallace
After torturing the Bulls for years with the Pistons, Wallace signed a three-year, $46 million free-agent deal with the Windy City club in the summer of 2006. Chicago thought it had finally found its center to pair with guards Kirk Hinrich and Ben Gordon.
In his first season with the Bulls, Wallace averaged 6.4 points and 10.7 rebounds. Chicago won 49 games and made the playoffs, where it swept the Miami Heat in the first round and then lost to the Pistons in the second.
The Wallace experience in Chicago went downhill after that first season. The Bulls traded Wallace to the Cleveland Cavaliers on February 21, 2008. His stint with the Bulls lasted just 127 games.
2. Dwyane Wade
The Bulls finally got their superstar player in free agency.
Except, this was an old Wade and he was just signing with the team for a money grab to get back at Miami Heat president Pat Riley.
Wade signed a massive two-year, $47 million deal with the Bulls, who had just traded Rose to the New York Knicks. The team should have traded Jimmy Butler, too, and embarked on a rebuild.
Instead, the Bulls signed Wade to a lucrative contract and added Rajon Rondo as well.
Wade averaged 18.3 points per game in his one season with the Bulls. Chicago went to the playoffs but lost to the Boston Celtics in the first round in six games after taking a 2-0 series lead.
The Bulls and Wade had to agree to a buyout after Chicago traded Butler to the Minnesota Timberwolves in the summer of 2017. Wade got to play in his hometown for a season while making millions. Not bad.
1. Eddie Robinson
Bulls GM Jerry Krause gave Robinson a five-year, $32 million contract in the summer of 2001. This was after Eddie averaged 7.2 points and 2.9 rebounds in his first two seasons with the Charlotte Hornets.
Robinson played in 144 games for the Bulls before John Paxson convinced Jerry Reinsdorf to buy out the remaining two seasons of the deal. That is how bad this signing was, folks. Chicago paid Robinson to go away.
Robinson never played in the NBA again. His reputation took a fatal hit after being out of shape and getting into arguments with Bulls coaches.
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