Scottie Pippen is one of the greatest small forward of all time, winning 6 NBA championships with the Chicago Bulls over his illustrious career. The 7-time All-Star was the Robin to Michael Jordan’s sidekick for a side that was the force in the league for nearly a decade. Perhaps other than the Golden State Warriors with Kevin Durant, the Chicago Bulls team that Pippen played for might be the best team ever.
Pippen is also extremely underrated, mainly because he played in Michael Jordan’s all-encompassing shadow. Jordan is by far the greatest player of all time and anyone compared to him is always going to look like a secondary piece, but Pippen brought incredible intangibles to the Bulls teams in the 90s. For one, he might be the best defensive wing of all time. Pippen made 10 All-Defensive Teams and also led the league in steals in 1995, and had the ability to defend 4 positions at an elite level. Scottie was also the primary playmaker for the team, averaging 5.3 APG during his stint with the Bulls and also chipping in 6.7 RPG.
No slouch as a scorer either, Pippen averaged 17.7 PPG during his time with the Bulls and was required to put the ball in the basket whenever Michael was getting hounded by multiple defenders. Even if many believe that Jordan “made” Pippen into a superstar, there are not 6 rings on Michael’s fingers without the former No. 5 overall pick. As valuable as Scottie Pippen was, there was also some tension between him and the Chicago Bulls organization. Whether it was getting severely underpaid or failing to get his recognition playing alongside Jordan, it almost led him away from Chicago in 5 blockbuster deals. Here are the 5 times that the Chicago Bulls traded a top-75 player of all time in Scottie Pippen.
5. Seattle SuperSonics - 1994
Trade Package: Shawn Kemp, Ricky Pierce, No. 11 Pick for Scottie Pippen, Will Perdue, No. 21 Pick
With Michael Jordan retired, the Chicago Bulls were seriously considering going into a full rebuild. Jerry Krause was considering a blockbuster deal that would bring Shawn Kemp to Chicago and Scottie Pippen heading to Seattle. Pippen was considered a secondary star, and the Bulls did not feel they had enough to go after championships without the best player in the world. Acquiring an All-Star in Shawn Kemp would keep the Bulls relevant even during the rebuild because the big man was only 24 years old at the time.
In addition, Chicago was getting two-time 6th Man Of The Year Ricky Pierce. Pierce was coming off a season where he dropped 18.2 PPG in 72 starts, but he would start declining during the 1994 season so the failed move was actually beneficial for the Bulls in that regard. Still, had Chicago pulled the trigger, Shawn Kemp would have been a Bull for at least the next few years and Pippen would have formed a dynamic duo with Gary Payton.
Nobody truly knows if the Bulls would have won 3 more championships with Jordan and Kemp, although that duo would have been very exciting to watch. Kemp and Payton were actually a great duo and made the NBA Finals together, but they could not get past Michael Jordan quite fittingly, Jordan is recognized as a star that would have won at least 6 championships with any other All-Star alongside him, so many Bulls fans believe this deal would not have changed much in the franchise’s history. But when looking at Kemp and Pippen’s ages at the time, a deal could have been beneficial for the Bulls. Kemp was 3 years younger than Pippen which meant when Jordan was 32 years old in 1996, the big man would have only been 28 and in his prime as a lob partner and paint presence.
4. Los Angeles Clippers - 1995
Trade Package: Multiple First-Round Picks for Scottie Pippen
Details of this deal were not released, but it was mentioned that multiple first-round picks would have been sent Chicago’s way in return for their superstar small forward. People were shocked when Pippen even considered the Clippers, an organization known as the “noisy neighbors” of the Lakers without the success that the Purple and Gold have had. In many ways, Pippen joining the Clippers would have been a disaster for him. But the swingman was seemingly interested in joining Los Angeles, if not for a former teammate’s advice.
It was reported that former teammate Ron Harper described Los Angeles as a bad fit for Pippen, and not an organization where he could prosper as he did with the Bulls for years. It ended up serving Pippen well because once Michael Jordan came back for a full season, they won more championships. Pippen could have been the catalyst for the Clippers’ organizational change and attitude towards winning, but it seemed unrealistic based on their track record.
Other than a slew of draft picks, details on which players were involved in this deal were not announced. Pippen wanted his own team and change of scenery, and Los Angeles always welcomed top stars who were looking for new homes. The Clippers missed out on Pippen and that meant many more years of mediocrity followed until Chris Paul formed “Lob City”. Meanwhile, the Bulls did the correct thing not going for a rebuild because they would win 3 more championships when Jordan returned from retirement.
3. Phoenix Suns - 1995
Trade Package: Dan Majerle, Wesley Person, Two First-Round Picks for Scottie Pippen
A deal that would have broken news outlets everywhere, a deal that would send Pippen to Phoenix would have been massive. Charles Barkley was already an MVP-caliber star with the Suns, and joining Pippen in their primes would have been very intriguing to watch. Of course, Barkley and Pippen would go on to play with each other in 1999 but that was, in many ways, 4 years too late.
Barkley was a machine with Phoenix, coming off a season where he put up 21.6 PPG and 11.2 RPG while making his 8th straight All-Star Team. Pippen was arguably the best defensive wing in the NBA and his duo with Charles would have been particularly dominant. For Chicago, they were certain they were getting a decent deal at the time. Dan Majerle was a much better shooter than Pippen but did not offer the playmaking or defense that the latter brought to the table. Wesley Person was a promising rookie and ended up making the All-Rookie Team, but his career ended up being underwhelming. Person would have his career season in 2002 by averaging 15.0 PPG but would average under 10 PPG 4 seasons out of 11 played.
The two first-round picks were the biggest selling point for the Bulls, but they ended up not taking the bait. Pippen was truly a unique player because of his size and skillset, and giving him up for a fringe star in Majerle and a promising but unproven rookie would have led to an immediate rebuild. Even if Pippen wanted to play with Charles Barkley, this deal never truly had a chance at going through.
2. Boston Celtics - 1997
Trade Package: Antoine Walker, No. 3 Pick for Scottie Pippen And Luc Longley
A deal that many Chicago Bulls fans would have prayed for, Jerry Krause almost pulled off a massive trade that would have set them up for years to come. Antoine Walker was a very intriguing rookie and ended up making the All-Rookie Team by averaging 17.5 PPG and 9.0 RPG. Of course, Walker would make the All-Star Team the following season by averaging 22.4 PPG and 10.2 RPG.
While Walker was a very good player, he was not enough to force the Bulls to give up Pippen and Longley. The No. 3 overall pick would have made this deal an absolute gem because the Bulls would have likely selected future Hall of Famer Tracy McGrady. With a draft filled with talent including Tim Duncan, McGrady, and Keith Van Horn; the Bulls would have rebuilt with Walker and McGrady on the squad. With Jordan fresh off retirement and winning more titles, that trio would have been unbeatable.
While Pippen was the biggest fish in this trade, Longley was also a big part of the deal. The big man provided a ton of size and defense to the Bulls team that was hard to replace, especially with the chemistry he built with the players. Pippen and Longley were a big part of the Bulls’ suffocating defense that stifled teams, but letting them go for a future Big three would have been a deal that would have altered history. McGrady and Walker would have extended Jordan’s career enough to possibly win even more chips, so many Bulls fans wished this deal went through.
1. Toronto Raptors - 1997
Trade Package: Tracy McGrady for Scottie Pippen
By far the deal that makes NBA fans’ mouth water the most was the deal that would have sent Tracy McGrady to the Bulls for Scottie Pippen. Chicago had a chance at acquiring McGrady in a Boston Celtics deal if McGrady was still available at No. 3 (which he was as he was drafted No. 9) but he was available straight up for them. A high-school phenom and clearly a superstar in the making, the Bulls would have had to take a risk in trading their 31-year old veteran in his prime for an unproven youngster. But if the Bulls made this deal, we might be looking at the best perimeter duo ever with Jordan and McGrady. Pippen and McGrady had similar builds and athleticism, except T-Mac was a natural scorer and slightly more explosive. McGrady never had Pippen’s defensive acumen, but he was massive levels above him on offense.
McGrady would take 3 full seasons before blossoming into a superstar player, but many believe a young version of the player was still good enough to help Jordan win more championships. Assuming McGrady would become the 26.8 PPG scorer in year 4, Jordan would have likely not retired and stuck around to enjoy an all-time great offensive player by his side.
The Bulls would win the 1997 and 1998 championships nonetheless, so keeping Pippen was not a bad move by any means. But if things were truly at a boiling point between Scottie and the Bulls organization, the best possible deal for them on the table was the services of Tracy McGrady. If the Bulls pulled the trigger on this trade, Pippen ends up playing with Vince Carter in Toronto while McGrady likely keeps Jordan in the league during the 1999, 2000, and 2001 seasons. That could have possibly meant that Michael and the Bulls could have 8 championship rings, but at the time it was a risk that was not taken.