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Alternate History

What if Jordan Joined a Different Team in 1999

Part 1

We talked about 1999 in the context of the last dance ending for the Bulls in the first edition of the series. We explored how it might have looked if Jordan never retired in 1993 or could have convinced the Bulls to run it back for a “2nd Last Dance” 1999, and even in 2000 or 2001 if they had try to hang on. As the Last Dance documentary established, Jordan said he still wanted to play in 1999. It’s not 20 year old lip service as he actually came back and proved it and did play again. With some pushing from 2 old friends, I think there was one spot that made sense and he could have possibly been convinced him to join in 1999.

Let’s look at the situation if the Bulls were still so hell-bent on blowing it up after the last dance, as it seems like they were, and Jordan couldn’t convince any of the major players and Jackson to return or ownership to pay them. I do think there was one viable landing spot that has never been mentioned for Jordan who clearly still wanted to play in 1999. Ultimately, I do think if Jordan was adamant about returning to the Bulls in 1999 and took it to the public they would have caved. They would have never been forgive for letting a vocal Jordan walk.

What would likely have to happen for Jordan to go to the Rockets is just never voice his opinions knowing what the Bulls front office and ownership wishes were, and have a clean break once Pippen was traded to the Rockets. The same Rockets with his good friend at the time Charles Barkley, now trusty sidekick for more than a decade in Scottie Pippen, and class of 1984 contemporary Olajuwon were on.

Before anyone says Jordan would never go to play for another stars team, I think you are looking at it myopically. The Rockets were coming off a 41-41 season in 1998 and Drexler had retired that summer. This wasn’t a good team, and they were years removed from likely their only championship if Jordan never retired. The Bulls or Jordan never lost to the rockets and would have likely beat them head to head in 1994 if Jordan never retired, giving Jordan even more, cover to go there as they would have never lost to them head to head.

It’s not like they were uniting in their prime, these guys were all 35 years old and at the end. I think it could be sold like it was at the time, as the old guys unite to take on the rising Lakers and Spurs. Jordan would eventually go to the Wizards, so is this really that outlandish to think he might like to play with Barkley and Pippen if he was pitched the idea, knowing he actually didn’t want to retire?

A fellow contemporary like Dominique Wilkins was playing for anyone that would sign him at that point. Karl Malone would leave the Jazz just a few years later and sign with the Lakers for almost nothing. Many other stars at the time were already pushing to get to certain teams to try to win. Barkley as well as Clyde Drexler for example, who had just retired on the Rockets that summer. It wasn’t unprecedented for stars to make guided moves to where they wanted to go by 1999. Jordan was also a free agent and free to sign anywhere.

The Salary Cap and being Paid more than Entire Teams

Michael Jordan through lucky timing and superstardom that raised the entire NBA’s profile was paid MORE than the entire salary cap in his last 3 seasons. Teams could pay their own players whatever they wanted under those CBA’s. There was no max salary. The Salary Cap was 27 million dollars per team in 1998 in his final season, and he got paid 33 million. Jordan was basically paid as much as the entire Jazz payroll that season, to put it into perspective. No other player exceeded 33 million until 2017-18 20 years later if you want your mind blown on just how much Jordan was paid at the time. This does make Bull ownership’s perspective on paying more understandable to me as well.

The point here is Jordan certainly didn’t need the money he had, made it. Had he wanted to do the Bulls a solid and take a minimum that year with them or anywhere else to make it happen, he could have. He was well on his way to being a billion dollar athlete and didn’t need to hold any team over the barrel at this point. If it were about the money, he wouldn’t have retired. We’ll just say as a free agent if he really wanted to get to the Rockets it was possible. The Rockets were about 5 million under the Salary Cap, they could have paid him well relative to most stars. Most stars were making about 10 million at the time, Barkley made 1 million this year. That’s respectable doable money to get Jordan to come, I think.

In the previous alternative history piece, we talked about Jordan’s Cigar injury, the impacts of the lockout season, and regression. If you want to read about that, click here. We’ll pick up with him on the Rockets.

The Rockets Team

So Barkley and Pippen convinced Jordan to join the team in January 1999 for somewhere between the minimum and 5 million dollars of free cap space just before the season starts. This is an old team but a formidable one with Rudy Tomjanovich as the coach and 4 Hall of Famers. Old farts sure, but still playing at a high level within the NBA of that time.

Here is the record and stat sheet of the Rockets that season without Jordan

31-195th Seed
Hakeem Olajuwon369.61.818.923.1
Charles Barkley3512.34.616.123.1
Scottie Pippen336.55.914.516.8
Michael Dickerson231.71.910.911.5
Cuttino Mobley232.32.59.912.2
Othella Harrington2560.49.816.1
Sam Mack281.
Brent Price3022.87.315
Eddie Johnson390.70.3410.2
Bryce Drew240.

Jordan was the league MVP the season prior. Even with the finger injury, given how well he played the first 45 games when healthy with the Wizards 3 years later, it’s very likely he is still playing just about at the same level he did in 1998. Perhaps even a little better since he dealt with a wrist injury in 1998 and had struggled to shoot in the regular season but had been better in the playoffs. If you added him to a starting line up of Olajuwon, Barkely Pippen, Jordan and 23-year-old Cuttino Mobley that’s got to be a title favorite. Without Jordan, the Rockets would lose to the Lakers in a close series 3-1, but one of the games was a 1 point loss.

You never really know how it works out, but Dickerson was a disaster in the playoffs as were Pippen and Olajuwon. Hakeem only averaged 13ppg vs Shaq this season, with a .461 True shooting. Yet they were still pretty close in the series and the games were competitive. If they had Jordan to carry the load, I think it puts them over the top. It is very likely they would have had enough to take out the Spurs at this point as well and cruise in the finals vs the 8 seed Knicks with Jordan. Presumably with Olajuwon who had played so well in the regular season looking much better vs a similarly aging 33 year old David Robinson who he had always punked. Shaq was entering his prime at that point and had just got the better of him. Unlike if Jordan had remained on the Bulls I think they lose to the Spurs in the Finals. On this Rockets team, I think with Jordan they win the 1999 championship, getting Barkley his 1st. It was just a better team had it existed than the Bulls.

2000 Rockets

In the actual history timeline, Pippen had been shipped off to the Blazers for a bunch of spare change to save money. That doesn’t happen if they win or contend. You keep Michael Jordan’s buddy around, and Pippen had settled into becoming a solid role player with the Rockets make up where he didn’t need to be the #2. Barkley and Olajuwon were still more than qualified.

Steve Francis

In actual history, the Rockets were able to trade for the #2 pick in the draft in 1999, Steve Francis. It was a different time in those days when you could get over in big ways on dumb GM’s. Francis also had the Grizzlies in a bad spot, claiming he wouldn’t play for them. In the end, essentially all the Rockets gave up of value was Dickerson, a 2003 1st Rounder and Brent Price and O. Harrington. Basically nothing. Francis was very good from day one as well, winning Co-Rookie of the Year.

Francis was adamant he would not go to Vancouver, so they still had to trade him, and there wasn’t apparently anything better out there. The Rockets would have still had the same package to offer even with Jordan or winning the title, and maybe the Grizzlies would have expected Jordan to be gone or not a great player by 2003 like they did Olajuwon and Barkely and still have done it. That’s actually what happened as Jordan wasn’t carrying a team to the playoffs anymore by then and retired that year. I suppose the Grizzles could be spooked about the pick in 2003 not being good if an ageless seeming at the time Jordan is still there. It’s certainly possible Francis ends up on the Rockets anyway, as the package is the same and Jordan is just as old as Olajuwon and Barkely. I think the trade plays out the same way.

We will assume Franicis was traded to the Rockets and Pippen is never trade. Here are how the players that would have been on the Rockets performed that season.

Steve Francis225.36.61818.4
Cuttino Mobley243.62.615.816
Charles Barkley3610.53.214.519.8
Shandon Anderson264.72.912.313.8
Hakeem Olajuwon376.21.410.316.7
Kenny Thomas226.11.68.312
Moochie Norris262.33.16.918.4
Matt Bullard322.51.16.811.9
Bryce Drew251.42.35.810.9
Scottie Pippen(added)346.3512.516.4

Pippen was much the same as the year prior, but this is the year Olajuwon really fell off in a big way with injury and missed almost half the season. It was mostly in December and he was back and would have been back for the playoffs. Barkley also got hurt in December and although he did comeback for one game in April it was ceremonial only to end his career. He had become overweight.

We’ll assume if Jordan was still there and playing at least at the level and likely a little higher he did the first 45 games with the Wizards this is still a playoff team with Francis and Mobley, Pippen and the game they got from Olajuwon and Barkley. Barkely would have probably comeback sooner more in shape and been able to play in the playoffs. He pretty much let himself go and was done when the team was knowingly headed to the lottery, He was still quite effective the games he did play.

This would have been an interesting playoffs. For one Mobley and Francis would have been able to pick up some of the slack and would lead a pretty solid 45 win team themselves the next year. Barkley wasn’t what he was the year before but he was still decent before his injury. Olajuwon could have fell into the same role David Robinson did at the end just concentrating on defense on a team like this. I think it would be a formidable team in the playoffs with Jordan and the other hall of famers playing roles around him with two young future stars, but a team that would lose to the Lakers or Spurs.


It probably would have been the end of the road in 2000 for Jordan and Barkley, but having some young guns to help them could have inspired each to stay if they were competitive in the playoffs. Olajuwon and Pippen were still above average starter level players the following seasons on winning teams, Olajuwon with Francis and Mobley leading it. It could have continued forward. if Jordan wanted.

Steve Francis236.96.519.921.6
Cuttino Mobley2552.519.517.7
Hakeem Olajuwon387.41.211.920.7
Scottie Pippen355.24.611.215.3

Still a very good core 4 to continue with. Barkely probably stays on one more year and puts up slightly fewer numbers and Jordan was still very good, and we know this from his Wizards’ timeline, which we are now butting up against. Wizards’ timeline where he could still put up 25ppg 6rpg, 5.0apg when healthy with them before his injury. Olajuwon had a bounce back season as well, getting his PER over 20.

There would be some questions how Jordan would coexist with Francis, as he needed someone to help him now that he wasn’t vintage Jordan. This was the year Francis established himself and there could have been some butting heads like there was in Washington with their young guys who kind of despised how Jordan rode them. Francis was a prickly personality to begin with. This is the year if could have gone up in flames with a strong personality guy like Francis and Jordan and their vision of the team. In the best scenario, they probably make it to the playoffs and even the 2nd round being a good 45 win team anyway without Jordan or Pippen, but the Lakers and Spurs were full force at this point. They aren’t winning the title. It’s over and Jordan likely retires or moves on to the Wizards, like he actually did with the Wizards the next season in real life.

Knowing how Jordan would do with the Wizards when healthy, and that he had a wrist injury during the regular season of the last dance in 1998 that suppressed his shooting some that year. I think it’s fairly easy to trace a believable career regression individually for such a consistent player like Jordan, I think we can project how he would do the years he missed or played only a few games. I’ve highlighted those years, I have filled in the blanks statistically.


That’s it. I think Jordan would have won his 8th title in this hypothetical if he had never retired in the 90s and joined the Rockets with Pippen. I thought he would have made it to the finals with the Bulls in 1999 if he returned there but that that team didn’t have enough to win the title in 1999, the Rockets did IMO. They likely lose to the Lakers or Spurs and never get close the other 2 seasons in 2000 or 2001. Had he stayed on the Bulls until 2001 he likely makes 2 finals perhaps even three in a weak East but doesn’t win the title in 1999 IMO.

In the next release, we will explore what if Jordan was drafted by the Portland Trailblazers or if the Blazers made an incredible trade that was actually proposed at the time of the draft. Hint Jordan was in it. It would have changed the history of the league and Jordan’s legacy, without a doubt.

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