It is an absolute wonder that the Chicago Bulls didn’t end up prematurely killing their dynasty by trading Scottie Pippen. General manager Jerry Krause shopped him to other teams on multiple occasions. Pippen publicly begged the Bulls for a trade on multiple separate occasions. The two sides bitterly feuded for years over everything from Pippen’s horrible contract to his 1997 decision to have elective surgery on his foot. All of the ingredients for a regrettable trade existed. 

And, to be fair, one nearly came. On three separate occasions, the Bulls came close to trading Pippen. On all three occasions, they wound up keeping him. But what if they hadn’t? What would have happened to the greatest dynasty in NBA history if it unnecessarily lost its second-best player? 

Let’s find out by going through each possible Pippen trade one by one. 

1994: Pippen is traded to the Seattle Supersonics

The trade: Chicago’s locker-room nearly fractured after Pippen’s notorious tantrum at the end of Game 3 of the conference semifinals against the New York Knicks. It was so bad that teammate Bill Cartwright fought through tears to scream at him in the locker room. As a result, the Bulls considered a trade with the Seattle Supersonics, which would have netted them Shawn Kemp, Ricky Pierce and the No. 11 pick in the 1994 NBA Draft in exchange for Pippen and their No. 21 pick, according to the Chicago Tribune. Sonics coach George Karl got Jordan’s approval on the deal, but it was ultimately squashed by Seattle owner Barry Ackerley at the last second over backlash from its fans. But what if it hadn’t? 

What it would have meant for the Bulls: A first-round pick is in far better hands with Krause than it was with Sonics GM Wally Walker. Whereas Seattle spent the No. 11 pick on role player Carlos Rogers, Krause, in this alternate universe, having already seen firsthand how valuable a bigger ball-handler could be with Pippen, selects Michigan’s Jalen Rose. Given their high hopes for Rose, the Bulls choose not to sign Ron Harper in free agency, and therefore keep B.J. Armstrong in the 1995 Expansion Draft. 

A core of Armstrong, Rose, Kukoc and Kemp is decent enough. The Bulls make the playoffs consistently for a few years, but never make much noise while there. The elephant in the room is Jordan, who returned to Chicago during the 1994-95 season in real life. In 2010, he told J.A. Adande that he probably wouldn’t have come back to play with Kemp, so in this scenario, he waits out the 1994 Major League Baseball strike, continues his development in the minors and eventually makes his way to the show as a member of the Chicago White Sox, albeit primarily as a ploy to boost ticket sales. 

What it would have meant for the Sonics: The Kemp version of the ’94-95 Sonics was excellent on offense (ranked No. 2) and decent on defense (No. 10). The Pippen version loses a dimension offensively, but is still quite good. Having another passer would have made life even easier for Seattle’s bevy of shooters, and a team that was already ahead of its time schematically would have become even more modern. Defensively, it would be arguably the best team in basketball, as Pippen is among the greatest defensive players in NBA history, while Gary Payton won Defensive Player of the Year only a year later. The real-life version also did fairly well against the two star centers that reached the Finals: Hakeem Olajuwon and Shaquille O’Neal. They held both to below their season scoring averages thanks to a deep rotation of bigs. 

Add all of that up, and you get a surefire championship team in this scenario. These Sonics bring home back-to-back titles in 1995 and ’96. Pippen is remembered primarily for his tenure in Seattle, and the titles generate enough sustainable fan interest enough to prevent a 2008 move to Oklahoma City. Jordan’s legacy is complicated greatly by Pippen’s success elsewhere. The occasional contrarian even uses Pippen’s Jordan-less championships to argue that he was the true leader of Chicago’s three-peat. 

What it would have meant for everyone else: By the 1996-97 season, every core Sonic except Payton would be 30 or older, and with two championships already in the bank, Seattle finally surrenders its crown to the Utah Jazz in 1997, who in turn fall to the Indiana Pacers in 1998 (one of only two teams to take a championship Bulls team to seven games in real life, along with the 1992 Knicks).

Without Jordan in his way, O’Neal leads the Orlando Magic to the Finals in both 1995 and 1996. Without a title, though, the same problems that plagued the real Magic lead to Shaq’s departure for Los Angeles. The Miami Heat take the Eastern Conference in 1997 before Indiana’s rise in 1998. 

Phil Jackson really told the Bulls in 1995 that he planned to leave in 1996 unless every player from the championship rosters was moved. Considering the mediocre roster this Bulls team possessed, he sees no reason to stick around and instead pursues his dream job. In March of 1996, the New York Knicks fire Don Nelson with the intention of pursuing Jackson in the offseason. He joins them soon after the Bulls are eliminated from the postseason, and while the union doesn’t produce a championship, it provides sorely needed stability in the NBA’s biggest market. Without Jackson on the market and desperately needing a big name to replace Del Harris, the Los Angeles Lakers turn their attention to the recently-retired Chuck Daly. In leading them to three consecutive championships to go along with the two he won in Detroit, Daly goes down as one of the greatest coaches in NBA history in this what-if scenario. 

1995: Pippen is traded to the Phoenix Suns

The trade: Things may have been bad after the 1993-94 season in Chicago, but they got quite a bit worse when the 1994-95 season commenced. The Bulls went into the All-Star break under .500 at 23-25, and, in a relic of a bygone era, Pippen gave Craig Sager a two-minute interview in which he publicly implored the Bulls to trade him. 

At the All-Star Game’s postgame press conference, Pippen named the Suns as an ideal destination. “Phoenix is a team that this could be their last title run,” Pippen said. “I could see them really pushing to try to make something happen.” Pippen continued to stoke the Phoenix flames until the deadline, at one point even saying it would be “paradise,” but he later admitted to Lee Shappell of The Republic that he had started the rumor himself. Let’s pretend that the two sides were interested enough to make the deal anyway. The basic framework of a deal would have sent Pippen to Phoenix for Dan Majerle, Wesley Person and draft picks. 

What it would have meant for the Bulls: This is perhaps the most complicated scenario to parse of any involving a Pippen trade primarily because of Jordan. In reality, he returned to the NBA on March 18, 1995. This deal would have come at the trade deadline, on Feb. 23. Jordan’s return was by no means guaranteed at that point, and if he didn’t want to play with Kemp, he likely would have had similar feelings about Majerle. But it would be naive to assume Jordan wasn’t already considering a return by late February, and with the baseball strike ongoing, basketball was still his best chance at removing himself from that uncomfortable situation in a way that he might not have even considered had the Bulls overhauled their roster in the 1994 offseason, when he was still playing in the minor leagues. And so, uneasy about his roster but intrigued by the idea of rescuing his wayward franchise, Jordan announces his return to the NBA in mid-March. 

It doesn’t go particularly well. Jordan leads the Bulls back to the postseason, but without Pippen, he stands little chance against the Eastern Conference’s remaining powers. The Bulls are decimated by the Magic in back-to-back postseasons. With Majerle declining and no realistic way for the Bulls to return to contention, Jordan enters 1996 free agency with a more open mind and ultimately accepts the one-year, $25 million offer from the New York Knicks that he turned down in reality. The Bulls are then forced to slink into a humiliating rebuild. 

What it would have meant for the Suns: Pippen would be so excited to get out of Chicago that things would start out fairly well in Phoenix. With Pippen to defend Clyde Drexler, the Suns even make it past the defending champion Houston Rockets on their way to the 1995 NBA Finals. Once there, though, they run into the NBA’s newest potential dynasty: Orlando. Phoenix simply doesn’t have the size to contain Shaq, and Orlando wins the championship in 1995. 

Things frayed quickly from there. In reality, Pippen loathed playing with Charles Barkley. The two spent only a single season together in 1999, and Pippen hated it so much that he asked for a trade after the season and absolutely roasted Barkley to the press. 

“I probably should’ve listened to Michael [Jordan] a year ago when he said that Charles will never win a championship because he doesn’t show any dedication,” Pippen told ESPN. “He’s a very selfish guy. He doesn’t show the desire to want to win. That’s my reason for wanting to get away from playing with him — because he just doesn’t show the dedication.”

In this scenario, Pippen and Barkley feud as they actually did, but rather than Pippen asking out, the Suns decide to trade Barkley instead. Just as they did in the real world, Phoenix sends Barkley to Houston for a package built around Sam Cassell and Robert Horry. Those two provide decent support to Pippen, but not nearly enough to keep the Suns in championship contention. When his contract expires in 1998, he resolves to find a new contender in free agency. Houston is out due to Barkley’s presence, but Sacramento, fresh off of acquiring Chris Webber and hiring Rick Adelman, jumps in with the cap space they originally saved for Vlade Divac. Pippen never wins a championship with the Sacramento Kings, but he at least gets the big contract he always wanted and contends meaningfully for several years. 

What it would have meant for everyone else: Buckle up everybody, because this is where things get wild. Sensing the need for a big-name coach for their eventual pursuit of Jordan, the Knicks bring Chuck Daly, his former Olympic coach, out of retirement in March after they fire Don Nelson. Daly vouches for another big-name acquisition, Dennis Rodman, whom he knows from their time together in Detroit. The Knicks trade Anthony Mason and Brad Lohaus for Rodman, still in San Antonio, rather than Larry Johnson as they did in reality. The loaded Knicks win back-to-back championships in 1997 and 1998. Jordan plays for two more seasons, but New York’s aging roster doesn’t allow it to contend any longer. Ewing retires as a Knick, and eventually the team builds a statue in his honor outside of Madison Square Garden. Jordan is hailed as the Reggie Jackson of his era, a legend who may have won elsewhere, but would forever be associated with New York. 

Jordan may have changed teams in the wild summer of 1996 in this scenario, but Shaq stays put. Having won back-to-back championships in Orlando, Shaq sees no reason to leave. The Lakers pursue Jordan, who prefers New York due to his close friendships with Ewing and Charles Oakley, and Alonzo Mourning, who ultimately remains with the Heat. The Lakers settle for Dikembe Mutombo. After eight years of coming up short in the hunt for a title, Kobe Bryant leaves the Lakers to try his hand at reviving the Los Angeles Clippers

In this alternate reality, Jackson leaves the Bulls a year after Jordan and lands with the Philadelphia 76ers. While Allen Iverson bristles at the constraints of the triangle offense, the Eastern Conference simply doesn’t have any other team capable of filling the power vacuum left behind by Jordan’s retirement and the aging of fellow contenders like the Heat and Pacers. Philadelphia reaches the Finals in 2001, but are vanquished by Tim Duncan’s San Antonio Spurs, who win four of five titles from 1999-2003 without the Lakers standing in their way. Indiana claims the 2000 title, which many consider asterisked due to Duncan’s meniscus injury. With additional championships in 2005, 2007 and 2014, Duncan retires with seven in total and a legitimate argument for the title of greatest player of all-time. 

1997: Pippen is traded to the Boston Celtics

The trade: As Jerry Reinsdorf explained in “The Last Dance,” Krause was ready to rebuild the Bulls after their fifth championship in 1997. Tracy McGrady has spoken openly about the fact that he nearly went to Chicago on draft night for Pippen, but he wasn’t even the biggest-name prospect heading to the Bulls. The rumored deal, according to the New York Times, would have sent Pippen to the Boston Celtics for both the No. 3 and 6 picks in the Draft. The two targets would have been McGrady and Keith Van Horn, whose future appeared far more promising at the time. Jordan got wind of the deal and axed it at the eleventh hour, according to McGrady. 

Reimagining a world in which this trade was completed is more complicated than the first two because Van Horn was selected No. 2 overall and therefore wasn’t on the board with either of the picks that would have gone to Chicago. He was later traded to Philadelphia, however, in a deal that included No. 7 overall pick Tim Thomas and veteran forward Jimmy Jackson. Krause, being the experienced draft-day trader he was (with his acquisition of Pippen ironically being the crown jewel of his resume), would have worked with Philadelphia to facilitate a similar deal. He would have selected Thomas No. 3 overall and packaged him with Kukoc, a similarly-aged forward that made far more sense alongside Allen Iverson than Jackson. He then would have selected McGrady No. 6. 

What it would have meant for the Bulls: Placating Jordan would have been nearly impossible given his loyalty to Pippen and Phil Jackson, who all involved knew would not last in Chicago beyond the 1997-98 season, but despite the controversy brewing behind the scenes, the new-look Bulls acquit themselves fairly well without Pippen. Chicago loses the conference finals to eventual champion Indiana and the teenaged McGrady hardly plays in the postseason, but Jordan is sufficiently impressed with Van Horn’s potential to return for the lockout-shortened 1999 season. As forgotten as he is now, Van Horn scored 19.7 points per game as a real rookie with the New Jersey Nets, and his shooting would have meshed very well with Jordan. The Bulls retain veteran free agents Steve Kerr, Luc Longley and Jud Buechler to make a concerted push for a championship, but Jackson is still replaced by Iowa State’s Tim Floyd. 

McGrady grows into a valuable enough role player in his second season to help nudge the Bulls past Indiana in a conference finals rematch, and they eventually topple the Spurs in the NBA Finals. Jordan sticks around for one more year to try for championship No. 7, and McGrady’s growth into a potential star makes it a distinct possibility, but Chicago’s frontline stands no chance against Shaq in the NBA Finals. Jackson gets revenge against his former team as coach of the Lakers and Jordan retires, but with McGrady and Van Horn in place as their long-term core, the Bulls attempt to replace Jordan in free agency with former Finals opponent Duncan. He says no, and the Bulls land Grant Hill as a consolation prize. Injuries to he and Van Horn push Chicago out of contention, but McGrady’s mere presence gives the Bulls long-term post-Jordan hope. 

What it would have meant for the Celtics: A lot of false hope. Pippen is still one of the best players in the NBA by the time he reaches Boston, but Rick Pitino is too trigger-happy to put a consistent roster around him. Pitino trades practically everyone except Pippen and Antoine Walker, and while that duo makes Boston a consistent playoff team, the Celtics never seriously contend for a championship under Pitino. 

That’s a bitter pill to swallow, because the true price of this trade for Boston isn’t the picks they’d haven given up. It’s Paul Pierce. A Boston team with Pippen would have been too good to pick No. 10 overall, where they landed their future franchise player. Once the brief Pippen-Walker era ends, the Celtics are forced into an extended tank, desperate to land the superstar they accidentally gave away. 

What it would have meant for everyone else: Boston’s loss is Orlando’s gain. Detroit, the team that picked after Boston in 1998, passes on Pierce in this scenario because they still have Hill and Jerry Stackhouse, but the Magic eagerly scoop up the Kansas wing. They fail to sign a max free agent in 2000, but that turns out to be a blessing. When Hill actually joined the Magic in 2000, he came in a sign-and-trade that cost Orlando Ben Wallace. No Hill means Orlando gets to keep Wallace, and one of the NBA’s best scorers gets paired with a four-time Defensive Player of the Year for the next decade.