Since entering the league nearly 60 years ago, the Chicago Bulls have been one of the NBA's premier franchises. Their most-successful stretch obviously came in the 80s and 90s, when Michael Jordan led a dynasty that won six titles in eight years with two separate three-peats. While they haven't had anywhere near the same success since then, they did have some fun seasons in the early 2010s with Derrick Rose leading the way before injuries derailed his career.
For the Bulls to achieve the success that they have, they've made plenty of savvy moves to put themselves in the best position possible. Not just in the draft and free agency, but also in the trade market. Some of their best moves have had them fleecing other teams, while others have resulted in a win-win situation for both clubs. Either way, Chicago has made more than a few fantastic trades in its history.
With that said, here are the five best trades that the Bulls have ever pulled off.
5. Bill Cartwright Trade, 1988
Bulls acquire: Bill Cartwright, 1988 first-round pick, 1988 third-round pick
Knicks acquire: Charles Oakley, 1988 first-round pick, 1988 third-round pick
Chicago had ascended to become a consistent playoff team at this time, but had yet to find the playoff success that would later define an era. To take that next step, the Bulls sought to add a top center to their lineup, and they had a target in mind. Cartwright had been a consistently strong option for the Knicks early in his career, but with Patrick Ewing coming into his own, he eventually lost his place in the starting lineup. Seeing an opportunity, the Bulls struck a deal.
Immediately, Cartwright established himself as a quality starting center once again. His stats weren't as spectacular as they were with the Knicks, but with the Bulls having plenty of scoring already, that was perfectly fine. In six seasons in Chicago, Cartwright averaged 9.2 points and 5.5 rebounds per game while playing a big role in the Bulls' first three-peat. After the 1993-94 season, Cartwright left in free agency to play the final year of his career with the Seattle SuperSonics.
Of course, the Knicks did pretty well in this trade as well. Over a decade in New York, Oakley averaged 10.5 points and 10 rebounds per game while making the NBA All-Defensive First Team in 1994.
While the two third-round picks never amounted to much of anything, the two first-rounders are a bit more interesting. The Bulls selected Will Perdue, who primarily served as Cartwright's backup and eventually became a key piece of another great trade on this list. Meanwhile, the Knicks selected Rod Strickland, who eventually became a solid NBA player but not in New York. All in all, a good bit of work from both franchises.
4. Luc Longley Trade, 1994
Bulls acquire: Luc Longley, 1995 second-round pick
Timberwolves acquire: Stacey King
Longley had been mostly a rotational player in his first few years, but as a former No. 7 overall pick and someone who stood at 7-2, he had plenty of potential to earn a starting role. The Bulls saw that potential, and swooped him up midway through the 1993-94 season. The decision to send off King, who had been a solid rotational piece during the first three-peat, was met with some controversy, but in 90s Bulls fashion, it worked out just fine.
Longley took some time to find his footing, but once Jordan returned in 1995, the Australian center asserted himself in the starting lineup. Longley averaged 8.9 points and 5.3 rebounds throughout his time in Chicago, and was instrumental to the Bulls' second three-peat.
As for the Timberwolves' side of this trade, they didn't do so well for themselves. King quickly declined in Minnesota, culminating with the Timberwolves releasing him just over a year after acquiring him.
While Dragan Tarlać, who the Bulls selected with the pick they acquired, never developed as expected, Chicago still did well in the long-term as well. In 1999, the Bulls traded Longley to the Phoenix Suns for four players and a first-round pick, which Chicago used on Ron Artest (now Metta World Peace). In both the short and long-term, the Bulls outright fleeced the Timberwolves and landed a key player to the second half of their dynasty.
3. Bob Love Trade, 1968
Bulls acquire: Bob Love, Bob Weiss
Bucks acquire: Flynn Robinson
Long before the Jordan era, the Bulls were just a fledgling franchise trying to find their footing in the league. They had some decent seasons to start out, but when they acquired Love in 1968, they finally had their first true superstar.
A three-time All-Star, Love averaged 21.4 points and 6.8 rebounds in nine seasons in Chicago. When his career came to an end, Love became just the second player in Bulls history to have his number retired by the team. Weiss also had a solid career with the Bulls, averaging 9.5 points and 4.3 assists in six seasons.
Don't feel bad for the Bucks, though, as they also did a bang-up job in this trade. Robinson had a good showing in Milwaukee, averaging 21.1 points in two seasons there. However, the real kicker is that the Bucks included him in a trade package for Oscar Robertson, a first-ballot Hall of Famer who helped them win the 1971 title. Overall, both teams got exactly what they wanted and more in this deal.
2. Dennis Rodman Trade, 1995
Bulls acquire: Dennis Rodman
Spurs acquire: Will Perdue
With Jordan's return in '95, the Bulls sought to make a big splash and get themselves back to a championship battle. By acquiring Rodman, who had previously been a thorn in their side with the Detroit Pistons, they did just that and then some.
Rodman kept up his dominant play when he came to Chicago, and with the offensive talent around him, it was a perfect storm. The eccentric center averaged just 5.2 points per game, but he was there to defend and dominate the boards and he did just that perfectly. Without the future Hall of Fame forward, it's entirely possible that Chicago's second three-peat never happens.
Unfortunately for the Spurs, they did not get anywhere near fair value back for Rodman. Perdue didn't develop into a full-time starter in San Antonio and averaged just 5.6 points and 6.9 rebounds in four seasons with the team. He even came back to Chicago as a free agent in 1999. The Spurs would start their incredible run under Gregg Popovich not long after this, but this deal continues to look awful in hindsight.
For the Bulls, though, it's hard to find a better trade than this one. However, there is one deal in their history that tops even this one.
1. Scottie Pippen Trade, 1987
Bulls acquire: Scottie Pippen, 1989 first-round pick
SuperSonics acquire: Olden Polynice, 1988 second-round pick, 1989 first-round pick
For as great as some of the other deals on this list are, there was no topping this one. This trade on the night of the 1987 NBA Draft set the Bulls up to dominate the league for nearly a decade, and it hardly cost them anything.
If you're reading this article, you know exactly who Pippen is so let's just cut to the chase. Pippen wasn't just Jordan's right-hand man throughout the Bulls' dynasty, but one of the best defensive players in league history. In 12 seasons in Chicago, Pippen was a seven-time All-Star and seven-time NBA All-Defensive First Team selection, while obviously helping the Bulls win all six titles.
While the deal lives in fame for Chicago, it does so in infamy for Seattle. Polynice lasted just over three seasons in Seattle and never became a key player, and 1988 second-round pick Sylvester Gray never even played a game with the franchise. B.J. Armstrong, a 1989 first-round pick and the one player the Sonics acquired that became an All-Star, did so for Chicago after another trade two years later.
Jeff Sanders, who the Bulls took with their acquired pick, didn't become a key player either, but when they got a player of Pippen's caliber, they could care less. With the impact this trade had on the Bulls and the NBA as a whole, there's no doubt that this is the best deal in franchise history.
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