15 Things You Didn't Know About Michael Jordan And Scottie Pippen's Relationship

No sporting dynasty revolutionized a sport quite like the Chicago Bulls of the 1990s. Six championships in eight years led by the most gifted basketball player of all-time, Michael Jordan. Throughout the decade Jordan was viewed almost as a sporting superhero. He flew through the air like no-one had ever seen, and was unstoppable at both ends of the court. Had he not retired (twice) when he did, who knows how many rings he could have added.

But before 1990-91, the year of the first Championship, Michael had already had six seasons in the league without so much as a Finals appearance. It took an outstanding coach, and the right ensemble of players to shape this extraordinary team, including Scottie Pippen. An argument could be made that behind Michael, Scottie was the next best player of the decade. But what made the Bulls so effective was the way Pippen and Jordan played together. They were almost telepathic on the court. So often in the NBA you see ego’s among the game’s best players clash when forced to work together as teammates. Pippen and Jordan always made sure that winning was the priority.

Despite their compelling partnership on the court, there have always been rumors that they never cared much for each other when the game was over. Here we have 15 stories that paint a much more complex picture. Jordan and Pippen shared a much more meaningful relationship than most people realized, and it was this relationship that helped foster the most devastating duo the league has ever seen.

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15 Jordan Made Life Hard For Pippen When He Joined The League

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It’s impossible to imagine how daunting it must be for a rookie to go to practice for the first time, having to justify the hype, the expectations. Imagine walking into training and the best player in the world is openly hostile to you. Michael was TOUGH on Scottie when he joined the Bulls. It went beyond the usual rookie-hazing. Jordan would trash Pippen in practice, humiliate him. He did this not because he thought Pippen didn’t deserve to be on the team. He did it because he could see the potential in him and realized that this could be the man who can help him win that elusive championship.

Pippen endured everything that MJ threw at him, and also observed the incredibly high standards Jordan set for himself. Jordan knew that not everyone was blessed with the same talent as he, but demanded that his teammates show the same level of determination he showed. Pippen learned this lesson more than anyone.

MJ’s methods worked. In his rookie year Pippen helped Jordan win his first NBA playoff series in 1988 against the Cavaliers. Cavaliers forward Larry Nance said that Pippen, “looked more like a three or four year veteran.”

14 They Would Play One-on-One After Practice

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While Jordan had ultimate respect for Pippen and what he did to help him win championships, he would never entertain the idea that Pippen was a better player than him. To prove this Jordan would often challenge Pippen to one-on-one after practice, particularly in Pippen’s early days with the Bulls. And the games would sometimes go as long as three hours.

Bulls guard Craig Hodges told the story of a practice session during the 1990 playoffs when Jordan and Pippen had an intense one-on-one session that seemed to never end. At this time Hodges said that Jordan toyed with Pippen, despite Scottie already being one of the elite players in the league. But he noted that Pippen just wouldn’t give up and keep going back. It was this experience that made Pippen such a fighter in the league. It could have got nasty, but such was the respect the two had for each other, it never went to that point. The one-on-one sessions seemed to be rarer later on in the decade. Perhaops MJ wasn’t interested in playing Pippen in his prime.

13 Michael Stopped The Bulls From Trading Pippen For Tracy McGrady

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Tracy McGrady was one of the hot prospects of the 1997 draft, selected ninth straight out of high school by the Raptors. Perhaps eyeing him as MJ’s heir in Chicago, Bulls GM Jerry Krause tried to arrange a trade with Toronto for Scottie Pippen. Krause even went as far as meeting with Jerry Krause to discuss terms of the move. However, MJ made the call to Krause and put an end to the deal, keeping Pippen in Chicago.

It is proof of the power Jordan had behind the scenes. He would only play one more year retiring after that 1997-98 season, and Pippen was immediately traded to the Rockets (for Roy Rogers and second round draft pick). After that season the Bulls went into the wilderness for almost a decade. You could definitely argue that Jordan and the Bulls may not have won their sixth title that year without Pippen, but with T-Mac leading the team during those post-Jordan/Pippen years would have been much brighter. And we would have seen a veteran Pippen play sidekick to the Air Apparent Vince Carter in Toronto.

12 They Were Both Heavy Gamblers

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Jordan and Pippen were game for a wager on almost anything, and Jordan would go to any lengths to win, even if it meant all-out cheating. There is the infamous Jumbotron trick Jordan played on Pippen. MJ would also bet his teammates at the airport on whose suitcase would come out first (Jordan would make sure he got to the airport staff to make sure they put his through first). Jordan’s coach at UNC, Buzz Peterson, also recalled inviting Jordan over to his home for a friendly game of cards. Even though there was no money on the line Buzz still recalled witnessing Jordan looking at Peterson’s mother’s cards while she was in the bathroom!

And once before a game against the Knicks, Jordan, Pippen, and teammate Horace Grant even bet on which one of their infant sons had a bigger “member.” The debate went on for almost 30 minutes before Jordan and Grant eventually conceded that Pippen was the winner.

11 Guarding Each Other In Training Made Them Two Of The League’s Best Defensive Players

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When your guarding one of the league’s best offensive player in training, it will do great things for your defending ability. And guarding each other in practice is what made Jordan and Pippen such stellar defensive players. Jordan was a nine NBA All-Defensive first team (winning Defensive Player of the Year in 1987-88 season), and Pippen made the All-Defensive team eight times. Both average more than 2.0 steals a game, and more than 6.0 rebounds a game. Defense is one area where Pippen was not in Jordan’s shadow, and guarding the world’s greatest player in training certainly helped mold Pippen into one of the league’s most feared perimeter defenders.

One key aspect of the Bull’s dominance was the sheer effort and determination that possessed Jordan, and he instilled the same mind-set in a young Pippen. Both understood that defense was a huge key to success. Jordan and Pippen would always score a bucket-load of points, so they put the work in training to ensure they were as effective as they possibly could be on defense.

10 They Made Their Teammate Toni Kukoc’s Life A Living Hell At The 1992 Olympics

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One thing that Pippen and Jordan shared in common is you did not want to get on the wrong side of either of them. Their careers are filled with tales of the great one’s getting revenge on players who showed them up on the court. And when they teamed up together it could be carnage.

Toni Kukoc had a rude introduction to life in the NBA. Drafted in 1990 from Croatia with big expectations before the Bulls won their first NBA Championship, Pippen was trying to negotiate a new contract, which Jerry Krause refused to give because he wanted to keep the salary space to sign Kukoc. Kukoc stayed on to play in Italy for 2 more years after being drafted, and Pippen eventually did got his contract. Everybody wins, right? Well, yes, but the resentment still ran deep, and when The Dream Team were due to play Croatia at the 1992 Olympics, both Pippen and Jordan seized the opportunity to put on a display to show Jerry Krause how insulting his decision had been. In these days before the genuine superstars like Dirk Nowitzski and Pau Gasol were in the league, there was a very condescending view of European players, and Pippen and Jordan were adamant of proving this point.

Even though Pippen’s contract had absolutely nothing to do with poor Kukoc, Pippen and Jordan absolutely terrorized Toni the entire game on every play. Kukoc ended up with four points in a 103-70 loss.

“I guess (the Bulls) see he’s not ready for NBA competition,” Pippen said after the game.

9 Jordan Would Trick Pippen Out Of Money On “Jumbotron Races”

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This one feels a like a bit of an urban myth. One thing we certainly know about Michael Jordan was that he was ultra-competitive in absolutely everything he did. Naturally this competitive desire would often be unleashed in the form of gambling.

A story circulated last summer, that Jordan worked out that the animated bull races on the Chicago Bulls Jumbotron were prerecorded, when he got to the arena early and saw workers watching it.

At games Michael would then bet Scottie $100. Because Jordan had already seen the recording he knew who was going to win so would never lose. Scottie, apparently, never worked this out and kept handing Jordan $100 each time there was race. Is the story true? Is Jordan really that brutal to his own teammate? Is Pippen really that stupid? Either way it’s a pretty funny story.

8 They Enjoyed An Occasional Pre-game Cigar

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Winning is often celebrated with a victory cigar. So confident were the mid-90s Bulls MJ and Scottie would have a victory cigar BEFORE the match. The iconic 72 winning Bulls team of 1996-97 faced the Washington Bullets in the first round. Before one of the games Pippen and Jordan pulled up in MJ’s Ferrari right next to the Bullets team bus smoking cigars. On their way to the locker room Chris Webber and Juwan Howard walked by in disbelief. In an interview with Dan Patrick, Chris Webber described the confidence, “It was almost like, ‘I lit the cigar. I’m celebrating already. This is just a formality, you guys getting on the court tonight.’”

Before another game during that series Webber said Jordan walked straight into the locker room with a cigar lit and asked “Who’s going to check me tonight?” All the Bullets could do was laugh at teammate Calbert Cheaney who was guarding Mike that night.

7 Neither Spoke To Dennis Rodman Off The Court The Whole Time Rodman Was In Chicago

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There are few bigger enigmas in the world of basketball than Dennis Rodman. Rodman played an integral part of the dominant 1995-98 Bulls, arguably the greatest ensemble ever to play the game. Interestingly off the court camaraderie was not a key ingredient to the team’s success. In the whole three years that Rodman played for the Bulls he did not have one conversation with Pippen or Jordan that didn’t take place on the court.

“I didn’t think it was important,” Rodman said in an interview with Yahoo sports in 2015. “I thought it was important for me to go there and win…I don’t have to have a job to speak to people.”

Both Jordan and Pippen were perhaps wary of Rodman when he arrived in 1995 due to his erratic history, which explains why they may have not been so outgoing. Rodman was also part of the “Bad Boy Pistons” who had an intense and fierce rivalry with the Bulls in the late 1980s/early '90s. But as long as the team was winning was all that mattered, which is why MJ and Pippen never sought to break the off-court silence.

It seems that Pippen is much warmer to Rodman these days, saying they share a great personal relationship. Rodman also made an appearance at Pippen’s 50th Birthday party in 2015 (Jordan wasn’t there).

6 They Had Dance-Off At Scottie’s 47th Birthday Party

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The greatest duo ever seen on the court don’t see a whole lot of each other these days, but when they do it’s always a moment to cherish. Watch how Jordan’s face lights up like a school boy when Pippen surprised him at Game 7 between the Heat and the Hornets in the 2016 playoffs.

In 2012 at Pippen’s 47th birthday, the internet was awash with a rumored “dance-off” between the two Hall-of-Famers. The party was a secret bash planned by Scott’s wife Larsa, and the battle took place at the end of the night reportedly to the Trey Songz tune “Say Ahh.” The fact there is no video phone footage of this moment is a modern tragedy, and to this day no-one knows who won, Pippen telling the Chicago Sun-Times, “I don’t know about that. I wasn’t the judge.”

5 Both Are Cheap

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One unfortunate trait that Pippen and Jordan share is a notorious reputation for being cheap. Charles Barkley said there are no two cheaper people. Scottie was so cheap he earned the nickname “No Tippen’ Pippen.” There are stories of Pippen opening huge tabs at bars, and making servers go above and beyond, and Pippen leaving no tip whatsoever.

Barkley told the story to Conan O’Brien two years ago of how MJ slapped Barkley’s hand away to prevent him from giving a dollar to a homeless person. “If they can ask you for spare change, they can say, ‘Welcome to McDonald’s, can I help you, please?’”

Pippen and Jordan’s relationship with money was probably instilled in them from their more modest beginnings growing up. Pippen was the youngest of 17 children, and was pressured into signing a long term deal, plus bad investments, which essentially left Pippen broke towards the end of his career. It’s no surprise that Pippen is so careful with his money. Billionaire Michael Jordan probably has less of an excuse!

4 Pippen Once Said LeBron Was Better Than Michael

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Arguments over who was the greatest player of all time rage daily on the internet. In a 2011 interview for ESPN’s “Mike & Mike In The Morning” show, Pippen added fuel to the fiery debate when he said, “I may go as far as to say LeBron James may be the greatest player to ever play the game.” Bulls fans particularly were shocked that Pippen could possibly hint that LeBron was a threat to Jordan’s dominance, and Pippen immediately took to Twitter to say that, “Don’t get me wrong, MJ was and is the greatest,” before adding “But LeBron could by all means get to his level someday,” which many would argue Lebron achieved in the 2016 finals.

More recently Pippen said in an interview with the Northeast Ohio Media Group that “I was LeBron James before LeBron James,” which you could take to mean that Pippen believes he was better than both of them.

3 Madonna Rejected Jordan For Pippen


Michael Jordan was notoriously competitive in every possible activity, whether it came to Game 7 of the NBA Finals, a card game, golf game, even the size of his hands (Michael always claimed he had bigger hands than Scottie which clearly is not true). There was one other area that Pippen had Michael bested, and that was size of his equipment down below. Bulls assistant coach Johnny Bach said, “that killed Michael…you should have seen the girls Pippen had waiting for him everywhere he went.”

According to Bach whenever the Bulls were in LA, Madonna would pick up Scottie in a limo complete with a hot tub. Michael clearly did not like how Pippen got to spend “quality” time with the most famous woman on earth, and used to tell Madonna he could satisfy her better than Pippen to which Madonna apparently replied “not a chance."

2 Pippen Was One Of The Few People He Worked With He Allowed In His Home

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There is usually only room for one superstar on an NBA team, and most like to keep it that way. When egos clash it can cause problems. As bitter as OKC fans are about Kevin Durant’s move to Oakland, the move probably worked out best for him and Russell Westbrook. Many have tried to paint a picture of Michael Jordan and Scottie Pippen as reluctant teammates, where jealousy and bitterness brimmed below the surface. The truth is they were actually very close off the court.

Despite being arguably the most recognizeable sports figure alive Jordan is an intensely private person who didn’t open up his home to his teammates. Pippen was one of the very few who saw the inside of Jordan’s home often going there to train and work-out.

In an interview with the Chicago Tribune after Jordan returned to Chicago out of retirement Jordan told the reporter, “I like having Scottie with me at the house. WE work out and talk, and he tells me all kinds of things. A lot of personal things. Scottie’s a very thoughtful guy, if he trusts you, and we really trust each other.”

Jordan paints a picture of how his partnership with Pippen was able to foster, based on trust and encouragement. Scottie and Michael were so in sync on the court, and their extraordinary partnership came from a much deeper and personal level than we usually see between teammates.

1 Scottie Chose Michael To Introduce Him into The Hall Of Fame

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Pippen has been dogged with abuse his whole career that he was Jordan’s “Sidekick” and only won championships because he was on MJ’s team. In 2015 Pippen got in a Twitter feud with Shaq who said that Michael “did most of the work.”

Pippen was one of the best players in the league when he played and could easily have let his ego get the best of him and be jealous. But the respect Pippen had for Michael never wavered which is why he selected him to introduce him before his induction into the NBA Hall of Fame. “I can’t think of a better person to do it,” Pippen said of Jordan’s introduction. “Michael is someone I shared my career with…He was a great teammate, teacher and admirer.” Considering the acrimonious split Shaq had with Penny Hardaway in Orlando and then Kobe in LA, he could have learned a thing or two from the way Jordan and Pippen never allowed their ego to get in the way of their success.

Pippen’s HoF induction was a final chance for Jordan and Pippen to share the stage one last time.

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