Since 1990, there has been no franchise in the NBA to match the level of success achieved by the Chicago Bulls. During the 1980s, the Bulls would transition from a franchise that had failed to appear in one NBA Finals into a dynasty that would win six NBA championships between 1991 and 1998, led by the greatest player of all time, Michael Jordan. It is hard to think that those dynasty days almost never happened until some key trades were made along the way to build the Bulls into the decorated franchise they are known as today.
Every team needs to make a deal at some point that puts them over the top as championship contenders. As one of the most successful franchises of all time, the Los Angeles Lakers have made plenty of these kinds of deals in their history as well. Over the years, the Bulls’ front office has done a great job at building a competitive unit on the court even beyond the Bulls’ dynasty days and preceding them. There are also instances where the best deals the Bulls ever made were the ones that never happened, such as trading Scottie Pippen and Michael Jordan during their second three-peat. Today isn’t about those deals, though. This is about the deals that went through and changed a franchise forever, delivering six NBA championships, the fourth most in NBA history.
These are the 10 best trades in Chicago Bulls History.
10. Charles Oakley
Credit: Fadeaway World
Bulls Receive: Charles Oakley, Calvin Duncan
Cavaliers Receive: Keith Lee, Ennis Whatley
On the night of the 1985 NBA Draft, the Chicago Bulls had their sights set on Charles Oakley out of Virginia Union University. When Oakley was selected ninth overall by the Cavaliers, Chicago swooped in with a deal for the rugged power forward that Cleveland could not refuse. The Bulls gave the Cavaliers their 11th overall pick Keith Lee who would go on to have just a three-year career due to a leg injury. They also gave Cleveland Ennis Whatley, who averaged 6.8 PPG, 7.0 APG, and 1.2 SPG over his first two seasons with the Bulls.
The Bulls landed Oakley, who would go on to become Chicago’s starting power forward almost right away. In his first three seasons in Chicago, Oakley averaged 12.2 PPG and 11.6 RPG in 241 appearances. Oakley developed a tight relationship with Bulls star Michal Jordan and helped the team make three straight All-Star appearances from 1986 thru 1988. Soon, Oakley would be on the other side of an extremely impactful trade in Bulls history, but we will get to that later.
9. Carlos Boozer
Credit: Anthony Gruppuso-USA TODAY Sports
Bulls Receive: Carlos Boozer, 2011 Second-Round Pick
Jazz Receive: Mario Austin
The next impactful trade for the Chicago Bulls came during the 2010 offseason. It was this offseason that the Bulls would acquire one of the better forwards in their team’s history, Carlos Boozer. Boozer had just come off a six-year stint with the Utah Jazz that saw him make two All-Star Teams and averaged 19.3 PPG and 10.5 RPG over that time. Despite being well-removed from his All-Star form, the Bulls acquired Boozer for a small price, and it proved to be the bargain they had been looking for.
The Bulls had to give up Mario Austin, their second-round pick from 2003, who would never see the court in NBA action. Boozer played exceptionally well for Chicago averaging 15.5 PPG and 9.0 RPG over the course of five seasons while helping them earn four playoff berths playing alongside MVP Derrick Rose and Joakim Noah. Boozer may not have been an All-Star anymore, but it was clear that he was capable of being an impactful player on a team playing winning basketball.
8. Chet Walker
Credit: Fadeaway World
Bulls Receive: Chet Walker, Shaler Halimon
76ers Receive: Bob Kauffman, Jim Washington
Chet Walker is one of the greatest players in the Chicago Bulls’ history. He spent the first seven seasons of his career with the Syracuse Nationals/Philadelphia 76ers from 1963 thru 1969, where he earned three All-Star selections and averaged 16.2 PPG. In 1969, Walker would be dealt to the Bulls in exchange for Jim Washington and Bob Kauffman, which would prove to be a massive steal for Chicago. Kauffman would never play a game for the 76ers as he was reacquired three days later and once again dealt that season for Bailey Howell. As for Washington, he would play two and a half seasons with the Sixers averaging 12.9 PPG and 9.0 RPG.
Chet Walker found another chance to shine once he adjusted to his new role with the Bulls for the 1969-70 season. Walker would average 21.5 PPG or better in each of his first three seasons with the Bulls as well as earn four All-Star selections over his final six seasons with the team. Walker and the Bulls advanced to the NBA playoffs all six seasons that he was in Chicago, but he never got to add another championship to his trophy case after his 1967 title with the 76ers. Walker is still remembered as one of the Bulls’ greatest big men and one of the best trades they ever made in team history.
7. Zach LaVine
Credit: Jamie Sabau-USA TODAY Sports
Bulls Receive: Zach LaVine, Kris Dunn, Lauri Markkanen
Timberwolves Receive: Jimmy Butler, Justin Patton
One thing is for sure when it comes to this next deal, one team wishes they could go back and not pull the trigger on it. In 2017, the Chicago Bulls had come to an impasse with one of their star players, Jimmy Butler. His time with the franchise had run its course amid drama amongst Butler and the coaching staff as well as his teammates. They found a trade partner in the Minnesota Timberwolves who were willing to include future All-Star Zach LaVine in the deal, and the rest is history.
For Butler, his time with the Minnesota Timberwolves did not last long and ended with a tirade during practice that saw Butler torch the Timberwolves starters with the D-League squad and scream in the faces of Timberwolves management. For LaVine, he has spent the last six seasons with the Bulls and earned All-Star selections in both 2021 and 2022. He has averaged 23/5 PPG or better in each of his last five seasons with the team despite very minimal playoff success. LaVine has reportedly been unhappy with his role in Chicago, but after a massive deal in 2022, I am willing to bet that both sides figured it out.
6. DeMar DeRozan
Credit: Kamil Krzaczynski-USA TODAY Sports
Bulls Receive: DeMar DeRozan
Spurs Receive: Al-Farouq Aminu, Thaddeus Young, 2022 Second-Round Pick, 2025 First-Round Pick, 2025 Second-Round Pick
The next deal in Bulls history comes in the form of a sign-and-trade deal that was once labeled as the worst free agent signing in NBA history. See, the consensus opinion was that DeMar DeRozan’s best days were behind him as he headed into free agency during the 2021 offseason. He had been silently operating on a less-than-mediocre Spurs team from 2019 thru 2021, and it looked as if he was headed for a very minimal role wherever his next stop would be. This is where the Bulls stepped in.
Chicago ended up risking a ton of capital in DeRozan, who rewarded them immediately for their gamble. DeRozan would not only silence the haters, but he would become a legitimate MVP candidate and All-Star once again. He averaged 27.9 PPG on 50.4% shooting and led the Bulls to the NBA playoffs. In 2023, which was his second season with the team, he averaged 24.5 PPG and became an All-Star again for Chicago. The Bulls missed the playoffs as a franchise riddled with injury and desperately trying to figure out which direction to go in. Still, acquiring DeRozan has been a home run of a deal.
5. Luc Longley
Credit: Fadeaway World
Bulls Receive: Luc Longley, 1995 Second-Round Draft Pick
Timberwolves: Stacey King
When this trade went down for the Bulls in 1994, most fans could not believe that a piece of their first three-peat from 1991 thru 1993 was headed out the door. In return, the Bulls landed Luc Longley, a 7’2’’ giant from Australia who would prove to be instrumental to the franchise over the next few years. Heading out the door was Stacey King, power forward and center who came off the bench for the Bulls from 1990 thru 1994 and averaged 6.6 PPG and 3.3 RPG.
Longley would have to earn the respect of not only the Chicago fans but the Bulls core of Michael Jordan and Scottie Pippen as well. Eventually, he would as Longley became a key starter for all three of the Bulls’ NBA championships from 1996 thru 1998. Longley averaged 7.6 PPG, 4.7 RPG, and 1.0 BPG across all three championship playoff runs and is a widely respected and honored member of Bulls history to this day.
4. Bill Cartwright
Credit: Fadeaway World
Bulls Receive: Bill Cartwright, 1988 First-Round Pick, 1988 Third-Round Pick
Knicks Receive: Charles Oakley, 1988 First-Round Pick, 1988 Third-Round Pick
The next greatest deal in Chicago Bulls history actually ended up working out for both sides of the trade between the New York Knicks and Chicago Bulls. The Bulls had decided to part ways with enforcer and power forward Charles Oakley, who would go on to become a key piece of some of the best Knicks teams in the last 50 seasons. The Bulls had their sights set on Knicks big man Bill Cartwright, who they were elated to receive in the deal.
Cartwright was asked to do much less on the offensive side of the ball in Chicago than he was in New York, considering the offensive firepower the Bulls already possessed. Instead, Cartwright embraced the role of the rough and physical presence in the paint and made sacrifices in his individual game for the success of the team. Cartwright’s defensive presence and job on the glass would prove to be instrumental in the Bulls’ three titles from 1991 thru 1993.
3. Bob Love
Credit: Manny Rubio-USA TODAY Sports
Bulls Receive: Bob Love, Bob Weiss
Bucks Receive: Flynn Robinson
Before Michael Jordan became the GOAT of the Chicago Bulls and the entire NBA, Butterbean Bob Love was one of the players vying for that spot after coming over in a trade with the Milwaukee Bucks. The deal saw Milwaukee land Flynn Robinson in exchange for Love, and he would become an All-Star averaging over 20.0 PPG in both seasons he spent in Milwaukee. Robinson was then used by the Bucks in a deal to acquire Oscar Robertson which directly led to them winning the 1971 NBA championship.
Love would become a superstar with the Bulls from 1969 thru 1977. Love would make three straight All-Star selections with Chicago from 1971 thru 1973, averaging 24.7 PPG and 7.2 RPG during that time. Love would also earn two All-NBA Team selections and three All-Defensive Team selections with Chicago and ranks top 10 in team history in most major statistical categories.
2. Dennis Rodman
Credit: Fadeaway World
Bulls Receive: Dennis Rodman
Spurs Receive: Will Perdue
If there were any team that was familiar with Dennis Rodman when he was made available by the Spurs in 1995, it was the Chicago Bulls. Rodman had been a thorn in the side of the Bulls for many years during the late 80s and early 90s with the Detroit Pistons as a member of their Bad Boy teams that tormented Michael Jordan and a two-time Defensive Player of the Year. The Bulls had just been eliminated by the Orlando Magic in the NBA playoffs with an inability to defend both Shaquille O’Neal and Horace Grant simultaneously in the post. Rodman and the Spurs had been at an impasse with San Antonio, fed up with Rodman’s attitude and extracurricular activities.
It turned out to be a match made in heaven as the Bulls sent Will Perdue packing to San Antonio and embraced Rodman as one of their own. Immediately, Rodman was the clear missing piece for Chicago as they went on to win 72 games and sweep the Magic en route to their fourth NBA championship. Rodman would win three straight rebounding titles with the Bulls from 1996 thru 1998 while also helping them three-peat as NBA champions over that same stretch.
1. Scottie Pippen
Credit: Matthew Emmons-USA TODAY Sports
Bulls Receive: Scottie Pippen, 1989 First-Round Pick
SuperSonics Receive: Olden Polynice, 1988 Second-Round Pick, 1989 First-Round Draft Pick
There is no trade greater in Chicago Bulls history than the one that Bulls Vice President Jerry Krause pulled off on NBA Draft night in 1988. For quite some time, Krause had his eyes on 6’8’’ forward Scottie Pippen out of Central Arkansas. Pippen was seen as the perfect compliment to Michael Jordan and perhaps exactly what the Bulls needed to get over the top as NBA champions. On draft night in 1988, Krause pulled off the deal for Pippen, sending Olden Polynice to Seattle along with two future draft picks.
Clearly, the deal worked out to perfection for the Chicago Bulls. Pippen would go on to become one of the great two-way players in NBA history, forming the greatest duo of all time with Michael Jordan. Pippen would help the Bulls win six NBA championships during his 12 seasons with the team, along with seven All-Star selections, seven All-NBA Team selections, and 10 All-Defensive Team selections. For Pippen, he found himself landing in the perfect spot in 1988 on that particular draft night. Would the SuperSonics be six-time NBA champions if Krause never made this deal?
