What If Michael Jordan Had Stayed Retired in 1995?

In March 1995, Michael Jordan returned to the NBA with a simple two-word fax: “I’m back.” But what if he had stayed retired?

MICHAEL JORDAN SHOCKED THE WORLD WITH HIS ABRUPT RETIREMENT IN 1993, but what if he had never returned to the game of basketball? What if there was no second threepeat, no 72–10 season, no late 90s return to glory for the Chicago Bulls? What if Jordan had actually left the NBA for good?

The 90s are littered with the corpses of other basketball greats who never reached the NBA mountaintop thanks to MJ. How many other greats would have broken through for that elusive ring, like Hakeem Olajuwon did in Jordan’s mid-90s hiatus? What would have happened to Scottie Pippen, and how would we think of Michael Jordan all these years later?

We already considered how things would have played out if Jordan had never retired in the first place. This week, we’re going in the opposite direction. What if MJ really did retire — and what if he never came back??

1993–94 SEASON

Jordan left the Bulls on the eve of training camp, but the Bulls weren’t exactly DOA. Scottie Pippen stepped up his game with his best season as a pro, putting up 22.0 points, 8.7 rebounds, and 5.6 assists a game. The Bulls returned largely their same team from 1993, replaced the GOAT with journeyman Pete Myers, and won exactly two fewer games.

Scottie finished third in the MVP race, and Horace Grant and B.J. Armstrong made their lone All-Star appearances. The Bulls pushed Patrick Ewing and the Knicks to Game 7 in the Eastern semis, but that was the end of the road.

We’ll assume the rest of the 1993–94 season played out the same. The Knicks came back from 0–2 to beat the Pacers in Game 7, then went to a third straight Game 7 in the Finals against MVP Hakeem Olajuwon and the Rockets, who outlasted the Suns in a Game 7 of their own.

The Knicks went up 3–2 at Madison Square Garden in a game no one actually watched on June 17 thanks to a famous white Bronco, but the Rockets returned to Houston and won the final two games by two and six points with John Starks shooting an ugly 2-for-18 in Game 7.

Of course, none of those teams were the best in the league in 1994. That would be the Seattle SuperSonics, who went 63–19 but were shocked by Dikembe Mutombo and the Denver Nuggets in the first ever 8v1 upset. Seattle ranked top-three on both offense and defense but missed their window, and East 1-seed Atlanta was upset by Indiana in the Eastern semis.

The 93–94 season was totally up for grabs, with the Rockets, Knicks, Sonics, Suns, Pacers, Bulls, and Hawks all legitimate title contenders. Play this postseason out again 100 times, and I’m not sure any one of them wins more than 15 times. Houston was probably something like the fifth or sixth best team, and David Robinson was a more deserving MVP than Hakeem, but hey — that’s why they play the games.

Nothing has actually changed yet, but it’s important to remember the context of that 93–94 season as we head toward a future without MJ.

1994–95 SEASON

Remember, the Bulls really thought Jordan was done; they spent big that summer on free agent Ron Harper to fill Jordan’s shoes. But with one hole filled, another opened. The budding superstar duo of Penny Hardaway and Shaquille O’Neal were enough to lure Horace Grant south to Orlando.

Chicago moved Toni Kukoc into a starting role where he put up 16ppg, but the team struggled to find its rhythm. The Bulls were 23–25 at the trade deadline, and Scottie Pippen had had enough. He wanted out.

Of course, the real-life Bulls got a two-word fax a few weeks later that brought Michael Jordan back and changed everything. Not so in our timeline.

In this alternate world, Jordan continues his foray into baseball, and the Bulls decide to rebuild around Kukoc and move on from the 29-year-old Pippen while they can still maximize his value.

This is where it gets fun.

There are plenty of real-life Pippen trade rumors to give us direction. Not all of them fit our timeline. Jerry Krause reportedly shopped Pippen in the 1997 draft — imagine shopping your star weeks after his fifth title in seven seasons — hoping to land high school star, Tracy McGrady. There was a rumored draft-day trade with Toronto, and another rumor had Pippen headed to Boston for the #3 pick (to take TMac). But those offers are years away.

Another rumor had Pippen heading to Phoenix for Thunder Dan Majerle, Wesley Person, and a couple picks. Perhaps Pippen would be enough to push Charles Barkley and Kevin Johnson to a title. Of course, it turns out Scottie made up that trade rumor himself.

Our Pippen trade is with another West contender.

George Karl wanted to break up Gary Payton and Shawn Kemp, and with Jordan gone, this was his opportunity. Kemp was 24 and coming off a seventh place MVP finish, but Karl wanted Pippen, and the teams had considered a swap that summer. Now Chicago decides to pull the trigger, rebuilding around Kemp and Kukoc, as Pippen heads to Seattle to bolster its title chase.

The real-life Bulls finished 47–35 but had MJ and Scottie instead of Kemp. They still make our playoffs considering 8-seed Boston was 35–47, but they’re not a real threat.

The East comes down to Orlando and Indiana. The Pacers had swept the Magic the previous season, but Orlando breaks through in seven with the help of Horace Grant, sending Shaq and Penny to their first Finals.

Pippen’s addition galvanizes Seattle and pushes them to a division title and 2-seed, ahead of Phoenix. The Suns beat the Lakers but lose to MVP David Robinson and the Spurs in the Western semis.

The Sonics sweep the Blazers and luck out when the 6-seed Rockets shock the 60-22 Jazz in a deciding Game 5. Seattle swept Houston 4–0 that season, and Kenny Smith was eaten alive by the Glove while Sam Perkins gave Hakeem problems by stretching him out on defense.

Seattle runs out a modern lineup of Payton, Kendall Gill, Detlef Schrempf, Pippen, and Perkins, with shooting all over the court and Scottie playing up a position, a true five-out offense with a pair of creators. The Glove swallows up Kenny the Jet, Pippen dominates an aging Clyde Drexler, and the Sonics advance in six to face the Spurs. It’s a similar story there. Payton always dominated Avery Johnson, but Sean Elliott typically gave Schrempf the business. Now he’s overwhelmed by Pippen, and Seattle’s shooting and defense is enough to outlast a stud center a second straight series.

The Sonics win in seven and go on to face Orlando, where Penny is swarmed by Scottie and Payton and Seattle continues its modern strategy, neutralizing opposing guards and wings and spacing the star big man out on D to create space in the first push toward a modern small-ball style with five-out and shooters all over the court.

Seattle wins in five, their first NBA championship since 1979. Scottie Pippen is named Finals MVP, finally atop the basketball world.

1995–96 SEASON

The real-life Bulls went 72–10 in Jordan’s first year back, but our MJ is still striking out for the Birmingham Barons. Shawn Kemp’s Bulls win 52 games instead, still good for a 4-seed. Phil Jackson leaves Chicago to replace the departed Pat Riley for his beloved Knicks, and New York goes 56–26 and takes the 3-seed.

Phil’s Knicks beat the Pacers, but the Magic dominate the Bulls again and this is Orlando’s East now. Patrick Ewing battles young Shaq to a draw, but MVP candidate Penny Hardaway is the new thorn in New York’s side as the Magic win in six to head back to the Finals.

The real-life Sonics traded Kendall Gill for Hersey Hawkins and made the ‘96 Finals, so we’ll swap for Hawkins here too. Those Sonics had the #8 offense and the #2 defense, and the D only gets better with Pippen in the fold. They’re the #1 overall seed entering the playoffs and fly through Sacramento and Houston en route to the Western Conference Finals.

David Robinson wins a second consecutive MVP for the 59-win Spurs but comes up short again in the playoffs as the Jazz pull the upset. Seattle played Utah in the real playoffs that year and went up 3–1 before beating them in seven. They got a big series from Kemp against Karl Malone, while Payton smothered John Stockton. Our Sonics will have to put Pippen on Malone, but that’s an uncomfortable mismatch on both ends, and Jerry Sloan is unwilling to adjust by going small with the Mailman at center.

Seattle has the mental edge now as the defending champ, and they got the job done in real life, so we’ll give it them here too. Seattle wins in seven, then wins the Finals rematch in six. Orlando is better now, but so are the Sonics.

Pippen wins a second straight Finals MVP for his work against Penny, giving him five titles in six seasons with a pair of Finals MVPs.

Wait, which former Bulls star was the player of the 90s thus far?

1996–97 SEASON

A frustrated Shaq leaves the Magic for sunny L.A. in free agency.

The Bulls drop from 69 real-life wins to just 48 with Kemp getting fat and Kukoc showing some age. Chicago drops to the 6-seed and begins to fade from relevance.

It’s Miami and New York atop the East now. The Heat are Pat Riley’s new team, complete with Alonzo Mourning and Tim Hardaway. The Knicks bring Ewing, Charles Oakley, and Larry Johnson, along with Phil Jackson. These teams met in real life, and the Knicks went up 3–1 before losing three straight. This time Jackson gives them the mental edge and they get the job done and head back to the Finals for the first time in three seasons.

The defending back-to-back champ SuperSonics try to reload in the offseason by trading for Charles Barkley, but they’re unwilling to give up both Hawkins and Schrempf in the deal. Phoenix sends Barkley to Houston instead, for Robert Horry and Sam Cassell in a big shakeup out West.

Those Sonics and Rockets met in real life, and Houston went up 3–1 and ended up winning a Game 7 in Seattle. This time, Barkley and Hakeem are too much for an undersized Sonics team, and the champs are finally dethroned.

Karl Malone is the MVP — and he deserves it this time — and the Jazz roll up 64 wins and coast to the WCF to take on Hakeem, Drexler, and Barkley. Of course, we got that matchup in real life, and Utah beat the aged Rockets in six, so why argue with reality?

The Jazz head to their first Finals ever, and this time they don’t have to face the GOAT. The Delta Center is rocking as the Jazz beat the Knicks to win their first NBA championship in front of the home fans in Game 6.

Karl Malone and John Stockton finally have their championship rings.

1997–98 SEASON

The 97–98 season saw a quartet of 60-win teams for the first time in NBA history. The Jazz and Lakers get there again in our timeline, but the Bulls and Sonics are very different teams now.

Chicago wins just 45 games en route to another 6-seed and first-round exit, the Jordan era feeling long ago now. Our Sonics miss Pippen half a season after that infamous summer surgery, and Payton and Schrempf are getting old. Seattle faces a Last Dance of its own, this one without MJ. They drop to 51 wins, falling to the 5-seed.

That leaves the Jazz and Lakers atop the West, with a rookie Tim Duncan and David Robinson pushing the Spurs. But San Antonio loses to Utah in the semis, and the Jazz move on to face a Lakers team featuring Shaq, Eddie Jones, and a sophomore Kobe Bryant off the bench. The real-life Jazz swept Del Harris’s Lakers, and there’s no reason that wouldn’t happen again. Utah heads back to the Finals to defend its title as Karl Malone pockets his second straight MVP.

The Pacers are best in the East now, winning 60 games with the arrival of veteran Chris Mullin pushing Reggie Miller, Mark Jackson, and Rik Smits to the next level. The real-life Pacers pushed the Last Dance Bulls to seven in the ECF.; here they face the Knicks and finally head to their first NBA Finals after playing in five of nine ABA Finals and winning three ABA championships.

Indiana ranked top-five on both offense and defense, and they had Dale and Antonio Davis to rough up the Mailman in the post. Utah sported the league’s #1 offense but was below average on D, and that’s the difference this time. Reggie Miller puts up an efficient 31ppg to help the Pacers to their first NBA championship.

Reggie wins Finals MVP and is rightfully recognized as one of the game’s outstanding players in the 90s, a top-three all time shooting guard.

Yet another Michael Jordan foe has won a ring in his absence.

1998–99 SEASON

Real MJ has retired again, so things are starting to head back toward the timeline we know.

The strike still happens, leaving us with a 50-game sprint to the finish. That leaves chaos in the East, where six games separate the 1-seed from the 8-seed. The West is more spaced out, with the Spurs, Jazz, and Blazers separating themselves from the pack.

The Lakers won 61 games the previous season but were punchless in the WCF, swept by the Jazz. The real-life Lakers needed to free up their starting SG spot for Kobe and traded Eddie Jones in March 1999 for Glen Rice. In our alternate reality, there’s a better wing available. Pippen-for-Eddie had long been rumored, and it finally becomes reality as Seattle moves on from its championship core and the Lakers add to theirs.

The Lakers fired Del Harris and replaced him with Kurt Rambis, but Kobe was not ready yet at age 21, and L.A. was poor defensively and flamed out in the Western semis with a Spurs sweep. Real-life Scottie is 33 and on the Rockets now — remember that? — but he isn’t enough to overcome the Admiral and Duncan as the Spurs win in six.

Karl Malone wins a third straight MVP, matching only Wilt and Russell, but the Jazz are upset by the Blazers and Arvydas Sabonis. Sabonis is no match for Admiral and Duncan, and the Spurs sweep Portland to head to the Finals.

The Knicks lose Ewing to injury and finish as the 8-seed, but Phil Jackson insists on playing through the post and this time, the 1-seed Heat outlast the Knicks 3–2 in the first round. Miami beats the Hawks, then knocks off defending champion Indiana.

The Finals feature the Miami Heat and San Antonio Spurs with two franchises in their first ever title chance. Alonzo Mourning is dominated by Robinson, Duncan does the rest, and the legendary Pat Riley is outclassed by some young upstart named Gregg Popovich. The Spurs win in six and the Admiral adds a Finals MVP to his two regular season MVPs, adding his name to the list of all time center greats.

Almost there…

1999–2000 SEASON AND BEYOND

The NBA struggles mightily at the turn of the century, thanks to the strike and consecutive titles by small-market Utah, Indiana, and San Antonio, but the Los Angeles Lakers come to the rescue.

A frustrated Phil Jackson leaves the Knicks and heads west to join his old Chicago protégé, and Scottie helps Shaq and Kobe threepeat as the Lakers return to prominence. Kobe goes on to win five championships and is eventually revered as the greatest shooting guard of all time. Phil finally gets titles #4, 5, and 6. Pippen gets #6, 7, and 8.

Scottie’s eight titles are third most all time, behind only Bill Russell and Sam Jones. Folks call Scottie Pippen the modern day Bill Russell, and he’s spoken of in the same breath as Bird atop the all-time SF rankings until some kid from Akron comes along. Everyone spends the 00s trying to find an elite two-way wing rather than a shooting guard chucker. Andrei Kirilenko and Shawn Marion are properly appreciated.

Karl Malone’s three consecutive MVPs place him atop the all-time PF list, and he passes Kareem Abdul-Jabbar as the all-time NBA leader in points. Along with that long awaited ring from 1997, Malone is nested safely among the top-10 players all time. So is David Robinson after two MVPs, two titles, and a Finals MVP. The Admiral is finally appreciated properly, and Hakeem becomes underrated with just the one random title run.

Malone, Hakeem, Reggie Miller, John Stockton, and Gary Payton all win championships in this timeline, no longer shut out by the BOAT.

Patrick Ewing and Charles Barkley still retire ringless.

Seattle celebrates their two 90s titles but struggles through the next decade before drafting Kevin Durant, Russell Westbrook, and James Harden in three straight years and moving on toward another decade of Sonics brilliance and repeated title runs.

Big Shot Bob is not a thing, and no one’s ever heard of Dennis Rodman or Steve Kerr.

There is no Warriors dynasty.

Michael Jordan retires as one of the all-time what ifs after leading the league in scoring seven straight seasons before retiring at age 30. He finishes with three MVPs, three titles, and three Finals MVPs, and most pundits agree that threepeat was enough to place him ahead of Bird and Magic in the all-time rankings, but 2000s Skip Bayless (Jim Rome??) vehemently disagrees. Most consider Kareem Abdul-Jabbar is the greatest of all time.

The Boston Sports Guy remains a local bartender, but Chicago sportswriter Jay Mariotti becomes Scottie Pippen’s greatest champion and promotes Scottie as the basketball GOAT, thanks to his incredible feat of eight rings in 12 seasons. Mariotti writes a big book about basketball and leaves ESPN to start a fledgling sports website, and he becomes increasingly insufferable as the Cubs and Blackhawks win championships in Title Town Chicago.

Mariotti talks about Michael Jordan as an all-time what-if baseball player too, but history has answered that question. Jordan makes the big leagues and bats .268 for the White Sox with 181 homers and 623 RBIs. He finishes his career with some large number of WAR and a wRC+ of whatever makes that random collection of letters good. The White Sox remain irrelevant, though a young Derrick Rose grows up playing baseball like his Chicago idol.

The Bulls remain irrelevant for decades too, but everyone remembers the GOAT player and team when Derek Fisher’s 2016 Warriors reel off 70 wins, replacing the 1972 Lakers as the best record in NBA history.

But unlike those Lakers, the Warriors don’t finish the job. Up 3–1 in the Finals, they blow three straight when LeBron James blocks Andre Iguodala’s shot and brings a title to Cleveland for the first time in 52 years.

This is the final line on LeBron James’s illustrious resume, and LeBron retires and heads off into the sunset with his third championship ring. Add that to five straight MVPs from 2009 to 2013, and there’s simply no arguing it:

LeBron James is the Greatest Of All Time.

This is the darkest timeline. ■

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