Scottie Pippen's feud with Jerry Krause, Bulls: A look at the events that led to star's departure from Chicago

Michael Jordan might be the star of ESPN's new documentary "The Last Dance," but much of the first two episodes were focused on his favorite teammate, Scottie Pippen. Despite a resume that makes him undoubtedly one of the greatest players in NBA history, Pippen's time in Chicago was marred by a pattern of disrespect and poor treatment from his own team. 

While the Bulls were winning championships on the court, Pippen was feuding with just about every major Bulls decision-maker off of it. At times, that included coach Phil Jackson. Owner Jerry Reinsdorf shoulders plenty of blame as well. But Pippen's fiercest enemy in Chicago was former Bulls general manager Jerry Krause. Their relationship grew so untenable that by 1999, the Bulls happily allowed their superstar forward to walk away in free agency after six titles. 

So what went wrong between Pippen and the Bulls? It's a long story that starts with a contract that would be utterly unthinkable in the modern NBA

June 17, 1991: Scottie Pippen signs the worst contract in NBA history

Calling Pippen's origins humble would be an understatement. He grew up in a small town in Arkansas with 11 siblings. His father was disabled after a stroke and his brother was paralyzed in a wrestling incident. Plenty of NBA players need quick paydays to support their families, but Pippen's circumstances were incredibly dire. 

The Bulls used that to their advantage. In 1991, they offered him a seven-year contract worth $18 million. At the time, the contract wasn't exactly egregious. But player salaries boomed in the 1990s, and it was apparent even at the time how quickly the deal would become obsolete. Pippen's agents, Jimmy Sexton and Kyle Rote, advised him not to take it, according to The Undefeated's Marc Spears. Bulls owner Jerry Reinsdorf claims to have done the same. 

But Pippen, in desperate need of financial security, signed the contract and almost immediately regretted it. Reinsdorf refused to renegotiate. By the time the 1997-98 season arrived, he was not only the sixth-highest-paid Bull, but only the 122nd highest-paid player in the NBA. Pippen's feud with the Bulls and Krause manifested in a variety of ways, but this contract was undoubtedly its genesis. Pippen was perhaps the second-best player in the NBA during the life of this contract and was paid as if he wasn't even a starter. 

July 27, 1992: The Toni Kukoc Game

Krause might have had Jordan and Pippen on his roster, but the apple of his eye was undoubtedly Toni Kukoc. A second-round pick out of Croatia in 1990, Kukoc was viewed by the Bulls as not only a potential superstar, but one more likely to play nice with the front office. 

The only problem was that Kukoc did not want to jump to the NBA immediately. The Bulls recruited him publicly for three years before finally luring him over from Croatia. Not only did that alienate Chicago's two incumbent stars, but it contributed to Pippen's poor contract. The Bulls had around $2 million in cap space earmarked for Kukoc while negotiating with Pippen, limiting the amount of money he could get. When Kukoc ultimately decided not to join the Bulls in 1991, Krause front-loaded Pippen's deal to save money for a future run at his former draft pick. 

Normally, such drama would play out behind the scenes. But in 1992, professional players were allowed to participate in the Olympics for the first time. Jordan and Pippen represented the United States. Kukoc played for Croatia. When the two teams met early in the tournament, Jordan and Pippen made a personal point of humiliating their future teammate. The two took turns defending him throughout the blowout. Kukoc, then one of the best foreign players in the world, was held to only four points. The message was sent: nothing Krause could do would wrest control of the Bulls away from Jordan and Pippen ... for the moment. 

May 13, 1994: Phil Jackson uses Pippen as a decoy

The 1993-94 campaign had a chance to be Pippen's signature season. With Jordan playing baseball, most expected the Bulls to falter. Instead, Pippen led them to 55 wins. He nearly won the MVP award in averaging 22 points, 8.7 rebounds and 5.6 assists to go along with his typically stellar defense. So when the biggest shot of the season arrived, Pippen justifiably assumed he would be the one to take it. 

He wasn't. At the end of Game 3 of Chicago's second-round series against the New York Knicks, Phil Jackson drew up the potential game-winner not for Pippen, but for Kukoc of all people. Jackson asked Pippen to be the inbounder. Pippen refused to re-enter the game. After years of being known as little more than Jordan's sidekick, his coach stole his opportunity to prove that he was something more. 

Kukoc hit the game-winner, but the damage was done. The Bulls lost the series in six games. Their locker room was fractured. So Krause considered a change. 

Summer 1994: Pippen is nearly traded for Shawn Kemp

Rarely do teams trading superstars manage to get one in return, but the Bulls nearly did. Ahead of the 1994 NBA Draft, the Bulls and Sonics discussed what would have been among the biggest trades in NBA history: Pippen to Seattle, Shawn Kemp, Ricky Pierce and a first-round pick to Chicago. 

Jordan advised Sonics coach George Karl to make the deal, Karl explained in his memoir, "Furious George." "Scottie can make your other players better," Jordan said. "Kemp can't." Karl wanted to make the deal. So did Krause. But Sonics owner Barry Ackerley couldn't pull the trigger. Kemp was too beloved in Seattle, and the public backlash was too great for him to consummate the trade even after Krause sweetened his offer. With no other worthwhile offers on the table, Pippen was forced to return to Chicago. This would not be the last time Krause attempted to trade him.

October 3, 1995: Bulls acquire Dennis Rodman

The Bulls roster Jordan returned to in 1995 was very different from the one he left. Championship mainstays like Bill Cartwright and Horace Grant were already gone. The entire rest of Chicago's 1993 championship roster would follow. Pippen was the only Bull to win all six of Chicago's championships alongside Jordan. The roster needed a complete overhaul. Krause's most daring move? Acquiring enigmatic superstar Dennis Rodman. 

Jackson revealed in his book, "Eleven Rings," that he asked for Pippen's blessing before the deal and he granted it. But on a 2019 appearance on ESPN's The Jump, Pippen explained that he initially didn't want Rodman on the Bulls. "It was a tough sell," Pippen said. "I definitely can say I wasn't overly excited to get him." That hesitation was well-founded. Rodman's original team, the Detroit Pistons, had knocked the Bulls out of the playoffs three times before their run of championships began. In the 1991 Eastern Conference Finals, Rodman committed a blatantly dirty foul on Pippen. 

Before the trade was made, Jackson made Rodman apologize to Pippen for the incident. He told the story to Darnell Maybury of The Athletic. 

"Once the trade was done, I went to Jerry Krause's house with Michael, Scottie, Phil Jackson, his dog, everybody else. We're at Jerry Krause's house and we're having dinner and stuff like that. And we basically didn't talk to each other at all. It was like 'The Triangle.' Michael sat here, Scottie sat here, I sat over here, and Phil's right in the middle. So we're at the house and nobody's talking to each other. So Phil comes over to me and says, 'Hey, Dennis, can you do me a favor?' I say, 'What is that?' He says, 'Can you go over there and say you're sorry to Scottie?' I was, like, 'What? Say what? I'm sorry to Scottie?' Phil said, 'You know, just go over there and soften him up a little bit, you know because of what happened in '91. You pushed him in the stands.' I said, 'You (expletive) gotta be kidding me, right? This is a (expletive) game.' He said, 'Just do it for me.' So I go up to Scottie and I say, 'Hey man, I'm sorry about what happened.' He said, 'Don't worry about it, man. We just want to win.' And that's how the deal got done."

Pippen explained in that ESPN interview that he quickly warmed up to Rodman, but the process couldn't exactly have been easy for him. Most teams don't acquire players their superstars are known to dislike. It wasn't the worst thing the Bulls ever did to him, but it certainly didn't help. 

June 25, 1997: Pippen is again almost traded, this time for Tracy McGrady

The Bulls were one of the NBA's oldest teams by the summer of 1997. A number of their players were also set to hit free agency after the 1997-98 season. So, as Reinsdorf described in "The Last Dance," the Bulls considered hastening the rebuilding process rather than pursuing a sixth and final championship. 

"After the fifth championship, which was 96-97, we were looking at this team and we realized, other than Michael [Jordan], the rest of the guys were probably at the end of their high productive years," Reinsdorf said. "We had to decide whether to keep the team together or not. And we realized maybe this was the time to do a rebuild and maybe not try to win a sixth championship."

Krause's plan to skip the ugly full-scale rebuild that he would eventually pursue after Jordan's second retirement was to dangle Pippen for a top pick in the 1997 NBA Draft. His target was a high-school phenom named Tracy McGrady. 

McGrady confirmed in a 2016 appearance on ESPN that the deal was very nearly completed, but at the eleventh hour, Jordan got wind of the deal and nixed it. All things considered, that worked out for the best for everybody. Jordan and Pippen won their sixth championship. McGrady got to grow up at his own rate in a Jordan-free environment, a fate that fellow high-school star Kwame Brown was unfortunately unable to avoid years later, when Jordan drafted him No. 1 overall in Washington before quickly souring on him and ruining his confidence. But Pippen likely wasn't thinking about his legacy at that point. He never forgave Krause for almost trading him. 

"That really is what tarnished my relationship with Jerry [Krause]," Pippen said in "The Last Dance." "He tried to make me feel so special, but yet he was still willing to try to trade [me]. He would never tell me that to my face. I felt insulted. I took the attitude of disrespecting him to some degree."

An already frayed relationship nearly fractured, and any lingering goodwill between the two sides was now gone. 

October 8, 1997: Pippen has toe surgery to protect his future earnings

Long before Shaquille O'Neal publicly declared that he "got hurt on company time, so I'll rehab on company time," Pippen pioneered the concept in Chicago. Rather than having foot surgery in the 1997 offseason or rehabbing the injury so that he could return quickly, Pippen opted to enjoy his time off and have surgery right before the start of the season. 

He didn't return until January, but as he explained in "The Last Dance," he had a good reason for waiting. At that point, he was only one season away from reaching free agency and achieving the financial windfall that had eluded him since that 1991 misstep. An injury could have risked that. It was a decision Jordan disagreed with. 

"Scottie was wrong in that scenario," Jordan said. "Scottie was trying to force management to change his contract, Jerry wasn't going to do that."

1997-98 Season: Pippen publicly berates Jerry Krause and demands a trade

Pippen's foot ultimately recovered, but his attitude never did. During the 1997-98 season, he took to publicly berating Krause in front of the team. Although we don't know what exactly was said, according to teammate Bill Wennington in "The Last Dance," Pippen "crossed the line." Considering the already extremely low standard for how Jordan and Pippen treated him, that's saying something. Jackie McMullan revealed on The Lowe Post that their nickname for him was Crumbs, because he always had muffin crumbs on his shirt. 

In November of 1997, Pippen publicly demanded a trade and claimed he would never again play for the Bulls. Chicago's interest in dealing him at that point is unknowable, but interest was likely minimal. Pippen's injury and pending free agency granted him extraordinary leverage. Why give up major assets for a player who might skip most of the season and then leave in the offseason? 

He ultimately returned to the Bulls, and Chicago won its sixth championship. But by that point, it was obvious to all those involved that the dynasty was over. The 1998 lockout delayed the timeline, but Jordan retired officially in January 1999. Krause had already assured Jackson of his fate before the season, and he was quickly replaced by Iowa State's Tim Floyd. All bridges in Chicago had officially been burned, so Pippen was left to find a new team. 

January 19, 1999: Bulls trade Pippen to Rockets

In January 1999, Pippen finally earned the massive contract he craved. Five years, $67 million from the Houston Rockets in a sign-and-trade agreement with the Bulls. Things didn't get much better for Pippen from there. With Krause out of the picture, he found a new portly nemesis: Charles Barkley. After only a year in Houston, he refused to continue playing with his Hall-of-Fame teammate. Ironically, he wanted to be traded to the Los Angeles Lakers so that he could reunite with Jackson, the coach who once denied him the biggest shot of his career. He ultimately wound up in Portland. 

Pippen played his last four productive seasons as a Blazer, and once Krause retired in 2003, the door was opened for a reunion. Pippen signed one last contract with the Bulls, a two-year, $10 million deal that could be viewed as a decision from Reinsdorf geared at repairing the team's relationship with its second-greatest player. By that point, Pippen was 38 and no longer a valuable player, while the Bulls were far from playoff contention. But for awhile, it appeared as if the superstar and his team made it through years of turmoil to get their happy ending. Less than a week ago, though, things turned back in a sadly familiar acrimonious direction. 

April 15, 2020: Pippen reveals he has been fired by the Bulls

Pippen never held a major role with the Bulls. He was not an executive making basketball decisions or a coach on their staff. But he worked for the team as many retired stars do: as an ambassador and an advisor. It's a mutually beneficial relationship that exists within practically every franchise. Legends get a paycheck, and in exchange, they keep the fans happy and provide expertise upon request. The job has virtually no stakes whatsoever. 

But the Bulls are in the midst of an organizational overhaul. They recently hired former Nuggets executive Arturas Karnisovas as their new top basketball executive, and he has begun the process of overhauling his staff. On the Thuzio Live & Unfiltered podcast Wednesday, Pippen revealed that he was a casualty of that process and has been fired by the team. 

What purpose firing such a hands-off employee might have served is unknown, but the decision is sadly in line with the callousness with which the Bulls treated Pippen for most of his career. 

Sam Quinn joined CBS sports as a basketball writer in 2019. Prior to that, he wrote for 247Sports and Bleacher Report. He is a New York native and NYU graduate who also has roots in Florida and California. Full Bio

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