4 Biggest Chicago Bulls Trades

min read
Dennis Rodman doing an interview during a convention in October 2018.
(Wikimedia Commons/Luke Harold)
Anatoly Pimentel @AnatolyPimentel Jul 23, 2023, 10:58 PM
  • Here’s a list of the biggest Chicago Bulls trades in franchise history.
  • Scottie Pippen leads the list of players Chicago received through trade.
  • Other notable players the Bulls received were Bill Cartwright, Bob Love, and Dennis Rodman.

One of the winningest teams in NBA history is the Chicago Bulls with six championships. These titles came during their 1990s run when they dominated the basketball odds by completing two three-peats from 1991 to 1993 and 1996 to 1998. Thanks to their eye for talent, they were able to draft his “Airness,” Michael Jordan, and he led them to the promised land multiple times.

But selecting great players through the draft was just one element to the team’s success, as they also showed an impressive ability to acquire talented players via trade. Chicago’s front office maximized its opportunity to assemble the best possible roster that put them in a position to win. Who among the trades in franchise history are the biggest? Here’s a top-four list.

Scottie Pippen

When Chicago drafted Michael Jordan in 1984, they instantly had championship aspirations. Jordan, however, couldn’t lift the team past the first round of the playoffs in his first three seasons. This prompted the team to look for additional help, and that help came during the 1987 NBA Draft when they traded Olden Polynice and two future draft picks to the Seattle SuperSonics for Scottie Pippen and a first-round pick.

Pippen was the perfect complement to Jordan’s game, leading to six NBA titles. “Pip” made it to seven All-Star Games and became a member of the All-NBA 1st Team three times. Pippen played in 865 games for the Bulls and averaged 17.7 points, 6.7 rebounds, and 5.3 assists.

Bill Cartwright 

Another key player to the first Chicago three-peat is Bill Cartwright, who was acquired by the Bulls via a trade with New York in 1988. Aside from the one-to-one player switch, the Bulls and Knicks also swapped their first-round and third-round draft picks. The 7-foot-1 big man became the starting center for the team and anchored the paint.

Although his production steadily decreased when he arrived in Chicago, Cartwright made his presence felt on the defensive end and scored points when needed. He played 397 games for the Bulls across six seasons and posted career numbers of 9.2 points, 5.5 rebounds, and 1.5 assists. The former third-overall pick finished his career with Seattle in 1995.

Bob Love

In 1969, Chicago brought a dynamic scoring forward to the team when they received Bob Love from the Milwaukee Bucks in exchange for Flynn Robinson. Along with Love, the Bulls also acquired Bob Weiss from the deal. “Butterbean” flourished with the team and displayed his potent offense to help them contend in the Eastern Conference.

Love spearheaded Chicago’s playoff run seven times, averaging a career-best number of 21.3 points, 6.8 rebounds, and 1.7 assists in 592 games. He was also selected to three NBA All-Star selections (1971 to 1973) and became a two-time member of the All-NBA 2nd Team in 1971 and 1972. Because of this legendary career with the Bulls, they retired his number in January 1994.

Dennis Rodman

After Cartwright’s departure and Jordan’s return from his basketball hiatus, Chicago needed another big man to provide intensity and defensive prowess, and Dennis Rodman fit the bill. In 1995, the Bulls agreed with San Antonio to acquire Rodman for Will Perdue. Prior to his arrival, the “Worm” was part of the Bad Boy Pistons that eliminated Jordan and the Bulls twice in the playoffs during the 1980s.

Rodman seamlessly supplemented the duo of Jordan and Pippen with his grit and hustle. His three-year stay with Chicago ultimately resulted in a three-peat, as he averaged 5.2 points, 15.3 rebounds, and 2.8 assists. When the Bulls dynasty ended in 1998, Rodman played for two more seasons before retiring.

Chicago Bulls Biggest Trades

Player AcquiredTrade DetailsYear
Scottie PippenBulls received: Scottie Pippen and a first-round pick / SuperSonics received: Olden Polynice, one first-round pick, and one second-round pick1987
Bill Cartwright Bulls received: Bill Cartwright and two draft picks / Knicks received: Charles Oakley and two draft picks1988
Bob LoveBulls received: Bob Love and Bob Weiss / Bucks received: Flynn Robinson 1969
Dennis RodmanBulls received: Dennis Rodman / Spurs received: Will Perdue 1995

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About the Author

Anatoly Pimentel

Read More @AnatolyPimentel

Anatoly Pimentel is an NBA and MMA writer previously featured in ASEAN Sports, Asian Persuasion MMA, and Overtime Heroics MMA. He graduated from Adamson University with a B.A in Communication and is a Web Content Writer for BetMGM.

Anatoly Pimentel is an NBA and MMA writer previously featured in ASEAN Sports, Asian Persuasion MMA, and Overtime Heroics MMA. He graduated from Adamson University with a B.A in Communication and is a Web Content Writer for BetMGM.