From A-list pickup runs to driving DC commerce, get an oral history of MJ’s journey from NBA champion to NBA owner in the first of Boardroom’s three-part series.
At 60 years of age, Michael Jordan has seen it all and done it all.
A baller, a billionaire, and a brand, His Airness has ascended to heights of ownership and affluence that kids still cling to and kings are measured by. However, 25 years ago, the world wondered what was next for No. 23.
Filling seats in Chicago for 13 lucky seasons and 610 consecutive sellouts, everything MJ touched turned to gold or green. Nike, the NBA, and the entire Windy City all relied on Jordan to make money and memories, providing hope for the hopeless and excess to the execs.
His fire-red blueprint for basketball and business is one with great risks and few blemishes.
All that equity and storybook ending hit the highest stakes in 2001 when Michael Jordan announced his return to the hardwood with the Washington Wizards.
Putting it all on the line when the nation was under attack and the league under duress, America’s hoop hero traded in his red cape and front office gig for a blue jersey and ice bags.
Leading a team that had only won 19 games the previous season, MJ bet his body, brand, and reputation for an uncanny partnership between GOAT and C-Suite, old icon and new market.
In the standings, it proved a failure. Looking beyond box scores, it was an economic event of massive proportions, reinvigorating an entire community, a global game, and a generation of athletes-turned-entrepreneurs.
Subscribe for the biggest stories in the business of sports and entertainment, daily.
Over the last three years, Boardroom has spoken to teammates, competitors, executives, and analysts who were around MJ’s transition from the backcourt to the front office.
This week, Boardroom offers a three-part oral history of MJ’s reign in Washington DC, beginning with his 1999 retirement and star-studded comeback training sessions.
A Cold Day in The Chi
25 years ago, hoops hell froze over.
“I think we were in a state of denial,” Dan Patrick told David Aldridge on ESPN. “Just like this city is.”
It was a frigid and fitting 23 degrees outside in Chicago. Inside the United Center, things were just as icy.
On Jan. 13, 1999, Michael Jordan announced his retirement from the NBA.
It was only days before the lockout officially ended and only months after he downed the Utah Jazz for his sixth NBA title.
“You just can’t believe somebody would go out on top,” Patrick said.
“We’re not used to athletes doing that. Here’s a guy who hit the Last Shot, won a title, was the MVP, and he says, ‘That’s it, I’ll step down.'”
“I thought about saying just two words, ‘I’m gone,'” the 35-year-old Jordan told the 800 media members in attendance.
“But I thought I owed my fans a lot more than that. Mentally, I’m exhausted, I don’t feel I have a challenge.”
Still, a .01% chance of return remained in sight.
“Physically, I feel great.”
Kevin Garnett (NBA champion, Hall of Famer, Host of KG Certified): When MJ retired? I was shocked because I knew he had a bunch of basketball left in him. He must be super bored, leaving the game?
Rachel Nichols (Award-winning Journalist, Host of Headliners): In the industry? We all knew it was coming. It still remains one of the biggest what-ifs in sports history.
Paul Pierce (NBA champion, Hall of Famer, co-host of KG Certified): I was sick. I always wanted to play against MJ and that was the year I got drafted.
My dream was to play at The Forum in Inglewood and to play against Mike. As soon as I come in? No Forum, no Mike.
Metta Sandiford-Artest (NBA champion, 1999 Chicago Bulls first-round pick): I was one year away and had the opportunity to play against MJ, Pippen, Rodman, Kukoc, BJ Armstrong … my favorite Bulls that I grew up idolizing.
But when Jordan retired? I just missed it and had to move on.
Garnett: It fucked up everybody because we were all fans — and still are — of Michael Jordan. He’s the GOAT of GOATs, the king of kings.
Everybody was looking around like, “Who’s gonna be the face of the league?” There were like seven or eight guys, and if I’m keeping it 100? Allen Iverson was kind of the face because he had so much influence on culture.
Nichols: For years, there was the question: who’s the next Michael Jordan? Harold Miner was Baby Jordan, Grant Hill — you could list off 10 people who were anointed the “Next Jordan,” which tells you just how desperately people were missing Michael Jordan.
The league office had declining television ratings to deal with.
Darren Rovell (Emmy Award-winning analyst, Sports Business Reporter): Game 6 of the 1998 NBA Finals was the most-watched NBA game ever. And then you head straight into the lockout. That’s a bad run.
In 2000 and 2001? I think it took LeBron’s draft in 2003 to get people going even though you had the Lakers titles. I think the lockout pissed people off and there was some attrition in NBA fandom.
Nichols: It was a huge hit. You had a league where the players weren’t playing and suddenly didn’t have Michael Jordan.
There was this feeling that a league that had exploded in popularity with Magic Johnson and Larry Bird and moved seamlessly there to the Michael Jordan years.
Suddenly, it didn’t have one of these gods of Olympus to carry it through the next era. It was a problem. It had an effect on the league economically, and it had an effect on the league in terms of culture dominance and where the NBA stood.
When MJ retired in 1999, the revolution was televised as ESPN aired the announcement, only to follow the live coverage with a 24-hour marathon of Michael Jordan highlights and homages.
According to The Chicago Tribune, economic experts estimated the league would lose anywhere between $100 million and $200 million due to MJ’s departure.
Rovell: The Bulls were the traveling Beatles, and then all of a sudden, it was John Lennon or Paul McCartney by himself.
Michael Wilbon (Award-winning Journalist, ESPN analyst): It was an event every night that he played for 15 years. It changed everything about the civic nature of the city. It changed race relations. It changed everything.
And more than that, it defined a lot of things about the city. It eliminated the second-city feel. We felt inferior to New York; Michael changed that and the energy of the city reflected that in his time there.
Nichols: The whole city ran through Michael Jordan. The fact that Michael Jordan was playing there was a claim to fame for the city globally. More so than anything that happened in that city prior, more than the World’s Fair! What city wouldn’t want to see itself in Michael Jordan?
You could see the way it changed where Chicago felt it was on the national scale compared to New York or Los Angeles.
Wilbon: The Chicago Tribune once did a story that Michael meant a trillion dollars to the economy of Chicago. A trillion! And it quantified it with economists and financial experts explaining why.
Having that type of presence converting a place 40-plus times a year? That’s a significant number of nights and days.
Rovell: When the Bulls became who they were, that’s when an economy popped up around the United Center — otherwise, it’s just in the middle of nowhere.
So, the economic impact is not only felt inside the arena but on the outskirts two hours before a game when people go to a bar before they go in. Or when people come into town just hoping they can scalp a ticket, just the demand to want to be in the arena or close to the arena.
Wilbon: There was nothing like the electricity that it brought to the city. Nothing.
You didn’t see the Bears in town, you saw Michael, Scottie, and Horace. Their presence just lit the place up and this happened for 15 years.
Rovell: The craziest thing that happened? Steve Schanwald, who was a top executive for the Bulls, basically manned the mailing list for the Bulls. The mailing list was of all the people who once got in or couldn’t get in.
It meant that when the Bulls were horrible for years and years after Jordan left the Bulls could come back to the mailing list and say, ‘Hey, you haven’t had a chance to come to the United Center, now come.’
Sandiford-Artest: We were losing games and it was packed.
Rovell: They led the league in attendance for years and years just from the Jordan halo that existed. If you look back at the early ’00s, the Bulls were still drawing 22,000 as they sucked.
Sandiford-Artest: The first year? Our plane was incredible. We had the leftovers from the championship team and each seat was a suite. It was incredible, it was the best plane I’d been on in the NBA — even better than the Dallas Mavericks plane. That Chicago Bulls plane was sick.
Garnett: All the luxuries we have today? All the structure we have in a lot of businesses? He initiated all that. He broke that boundary for us.
I know a lot of people will go back to Bill Russell, but Michael Jordan took us from where Bill Russell and Oscar Robertson took us to be universal. We were not only household names, but licensing went to another level.
The business of basketball went to another level because of Mike.
The Wizard of Ops
Michael Jordan started the new millennium in the front office AND the box office.
Months after retiring, MJ jumped to the biggest of big screens by brokering a deal with IMAX.
“Ultimate Jordan” aired in over 50 IMAX locations globally, making over $21 million as an art project and propelling his Chicago Bulls highlight reel across a 79-foot screen.
Back in America’s capital, the popcorn had long been popping.
On Jan. 19, 2000 — almost exactly a year after retiring from the Bulls — the GOATed guard was brought on as a part owner and president of operations for the Washington Wizards.
Among the worst teams in the entire NBA and amid a five-game losing streak, the announcement shocked former foes and peers alike.
At the same time the basketball world was questioning Michael’s move, he was challenging his new team, calling the Wizards rosters “underachievers.”
The next night, the lowly team got their first win in 10 days.
Nichols: It was pretty shocking that he was going to be with a team that in no way was synonymous with greatness. This is a team that last appeared in the NBA Finals in 1979! And had been on a downward trajectory ever since.
Wilbon: I was covering the league then, so I was around the flow of conversation. I wrote about it in The Washington Post from the Super Bowl. The news and buzz of it was crazy.
David Falk is my neighbor in Besdea. I was a member of one of the courses that Michael joined, Four Streams. Because of what I did and having the Chicago part in common already, he let me in on what was happening.
People thought it was going to change everything — and it should have — but it was temporary.
Garnett: Mike had on suits and gave a whole different perception. He determined how you came into camp and your whole mentality.
Nichols: Abe Pollin was an old-guard NBA owner who was a real fabric of the league establishment at that point.
He and Michael had some pretty contentious moments across the bargaining table during a previous lockout, so that surprised everyone. But he was someone who knew MJ well during their mutual time in power positions around the league.
Wilbon: I knew from the Wizards’ end of it that it was possible and it just made sense to me. When he came back and wasn’t playing — just being an executive — it made sense that the franchise needed the juice that he could bring to it.
Nichols: Abe was able to see the value in having Michael around the team and was willing to give up a lot financially to do it.
Back in Chicago, writers, fans, and friends felt Michael Jordan should’ve been given a job — or a piece — of the Bulls.
Finding greener pastures in DC, the benefit of working with the lowly Wizards was not only a front office title but a 10% ownership stake in the team. At that time, no NBA player had ever become an owner of an NBA team.
While Washington wasn’t ripe with talent as a franchise, it was a major market for basketball — and MJ.
Even after retiring from Chicago, Jordan was still the most valued endorser in America.
Before trading in his pinstriped jersey for pinstriped suits, the celebrated shooting guard signed a 10-year endorsement deal with WorldCom.
Said to pay him $2 million annually, MJ was making more a year in retirement from WorldCom than the bulk of the Bulls or Wizards were making a year from the NBA.
Slinging pre-paid calling cards and appearing ads, the 1995 signing took new shape in 1997 when WorldCom bought MCI for $41.9 billion.
Appearing in 80% of WorldCom ads, MJ was starring in phone service commercials while enjoying basketball retirement.
In the same span that WorldCom bought big on Mike, the nation’s capital opened up the $260 million MCI Center: the new home of the Washington Wizards.
Upon opening, the rebranded Bullets struggled to sell tickets due to a struggling squad.
When MCI’s main man Michael Jordan joined the front office, things suddenly shifted in the building and around the city.
Nyrik Lee (Former Wizards intern, Marketing Director at The Museum DC): For him to plant his flag in DC was crazy. It was damn near like what happened in 2008 when Obama came.
Having a figure like him in the area? Of all places to go? It was that type of feeling where everybody was shocked that this god-like figure was looming in the city. That any moment you could see him.
Nichols: A lot of times, he’d watch the games in his office on TV even though he’d be in the arena. But the times he was visible in the box? You’d have fans constantly shouting at him, “Come down on the court and play!”
He had missed being part of the game. The biggest thing about Michael’s Wizards tenure overall was that, for him, there was nothing like being part of the game night after night.
His first go was as an executive and part owner because once he retired the second time, that path was closed to him.
Nineteen years before becoming a businessman in DC, a young Mike Jordan studied cultural geography at the University of North Carolina.
Each offseason during his dominance as a pro player, he’d come back to Chapel Hill to scrimmage with NBA alumni and active members of the Tar Heel roster.
One summer after he made the move from All-Star to exec, he stopped by the Dean Dome to see some old friends and new talent.
Brendan Haywood (NBA champion, UNC All-American, NBA TV analyst): We all just knew about Michael Jordan as a player; we weren’t thinking about the front office aspect of it.
He came through on one occasion when I was in school. Mike had retired at that point, so it wasn’t like before when he was coming back all the time to stay in shape.
He was dominating the pick-up games. Jerry Stackhouse, Antawn Jamison, all these guys come back, and Mike’s out there dominating.
Afterward, we’re like, “You still been playing? You been training?” He goes, “I haven’t picked up a basketball since I retired.”
In Michael Jordan’s first two seasons in the Wizards’ front office, the team finished dead last in the Atlantic Division.
While attendance and morale were both up upon arrival, fans across the capital clamored for Mike to swap his sharp suits for a blue uniform.
Nichols: The team was not doing well, and here was a guy who could help them just by putting on a jersey.
There was a big cry in Washington to come back, and there was a big cry across the league for him to come back. There certainly was an itch with him.
He left basketball as the greatest player of all time. He wanted to get back to being the person he was when he was the greatest at something. That’s where you could start to see that he might come back.
I saw him various times over that period, and he was a little slimmer and Tim Grover was around. There were hints.
Jay Z, Beyoncé & Basketball’s Best Kept Secret
On April 18, 2001, the Washington Wizards ended a three-game losing streak.
It was only because the regular season concluded.
Downed at the hands of the Toronto Raptors, fellow North Carolina alum and Air Apparent Vince Carter controlled the game from the two-guard spot.
Scoring 34 points and sporting a shaved head and signature Nikes, he was like Mike in many manners.
The only Wizard who could stop Vinsanity was wearing not a jersey but a suit.
Perhaps it was time to grab his cape.
Antoine Walker (Three-time NBA All-Star, Chicago hoop legend): In 2001, I got a phone call back when you called people private. I was five years in the league, and I was the ringleader in Chicago as far as pickup basketball.
At this time, you’re talking about 20 or 30 pros that lived in Chicago. We all played pickup ball together. I ended up getting a call from Mike that he is thinking about coming back and wants to get in the gym.
We were playing in the park at the time. He wanted me to get the guys together and asked if we could move the run over to Hoops.
Quentin Richardson (NBA veteran, Jordan Brand ambassador, Knuckleheads co-host): We were part of the group that was in the gym when he was coming back.
There were straight killers in that building.
Pierce: I was always going to Chicago and playing in the pickup games with Mike and Antoine. Mike was playing every day.
When you have a gym with me, Toine, Shawn Marion, Jordan, Ron Artest? It was crazy in there.
Sandiford-Artest: Rookie year, I was in the gym. It was all new having pro training at the next level where players are faster, better, and bigger. I was mostly at the Berto Center.
I forget how I got the invitation, but I’m from New York City, and I’m always looking for runs.
Even in the prime of my career, I was playing on concrete multiple times a day. I never lost one game at the Rucker, and I have three championships there. I’m one of the best streetball players.
Not being in New York in the summertime was really challenging because I’m always playing basketball. In Chicago, when I got the opportunity to play in those open runs? I needed to play some basketball.
Walker: That was a surreal moment for me as a person and as a player. To be able to be with Michael Jordan on a day-to-day basis and train with him? That’s something I’ll remember for the rest of my life.
It was tough, but you had respect for what he was trying to do and accomplish. The gym was private but it was public because so many of us were from Chicago.
Despite MJ being an exec in Washington, the runs began to heat up in Chicago.
Back in DC, spirits were high. Not because of murmurs of a Michael Jordan comeback but because the Wizards won the 2001 NBA Draft Lottery, securing the No. 1 overall pick for the first time since becoming the Baltimore Bullets back in 1963.
All the while, MJ was doing his own evaluation of what basketball’s next generation was made of at Hoops Chicago.
To no surprise, the young guns were sizing up the old exec just the same.
Sandiford-Artest: He was very physical, and that’s about how it was playing streetball in New York City.
Guys like DP, The Predator, and The Terminator were super physical in New York. But Michael was psychical.
Now, everybody else in those runs? They were definitely not as physical as MJ.
Pierce: I was matching up with him. I wasn’t really talking, but he was. I was loving the fact that I had a chance to play against him because that was my dream since he retired.
Walker: He was 38. The competitive drive that he had to get back in great shape and compete? That was something special.
I think we all learned a lot from that. We learned a lot about that game of basketball and the passion it takes to win.
Sandiford-Artest: At 19 years old, my mindset was in a different place. I wasn’t really interested in much besides basketball.
He played well against me lots of times, and I played well against him a few times. It was always physical. Mike was older, and I was at my prime defensively. He had games where he played very well.
Antoine Walker was looking really good. Michael Finley was playing well, and Jerry Stackhouse played well. Corey Benjamin was there and a few big guys from the Bulls. Jamal Crawford was younger.
Jamal Crawford (Three-time NBA Sixth Man of the Year, TNT analyst): My dad had told me that Michael Jordan liked my game. But I didn’t believe him. How would he know?
We’re playing against Antoine Walker, Michael Finley, Penny Hardaway, Ray Allen, and Tim Hardaway.
One day, we had Charles Barkley on our team because at the time, he was thinking about making a comeback.
Sandiford-Artest: I played against Barkley one day. I don’t know if he was coming back, he was a little bigger and getting a run in.
LeBron James was younger — he fit in very well. I think he was 15; he got a test of the waters. I remember him attacking the basket, and I was like, “Wow.” I was 19 and I was not as athletic as him at 15.
LeBron had no problem. He didn’t have all the skills but in terms of attacking the basket on the fastbreak? I don’t recall anybody getting in his way.
Walker: Those runs were super competitive. Everything was well organized, well run, and we played with referees.
There were days when there were 35 pros! If you lose a game, you may have to sit two games to get back on the court. That’s how deep the competition [was].
So many guys in the gym could do so many things, but it was still traditional because, at that time, centers were still relevant. Mike picked his team, we’d pick our team, and it’s let’s go.
Sandiford-Artest: That was MJ and Tim Grover’s gym, so I’m assuming they made the rules — definitely even teams.
Crawford: I’m just a young dude; it wasn’t like he was stacking his team. I would’ve been one of the last picks just based on how young I was.
The next time I went, Tim Grover was calling me saying, “MJ’s waiting on you. He’s waiting to start the game until you get here.”
From that moment on? We didn’t lose one single game for two straight summers. We never lost. Never.
Richardson: I can neither confirm nor deny that. It got competitive.
Walker: [Laughs] Nah, they lost, but Mike won a lot. The days that Jamal was there? Now, that could be true. But I took pride; I wasn’t going to lose every day. But I got a few wins, too, now.
Sandiford-Artest: Mike was winning games for sure. He averaged 25! But that first year? You should’ve seen him in the gym; I thought he was going to average 35. That’s how nice MJ was in the gym.
Walker: We played every day at 2 p.m. for two or three hours. People would want to come in and watch, but Tim Grover ran the gym with an iron fist. He was really big on who we brought in, so we had to create a list.
Pierce: We would play cards after at Antoine’s house, and he was talking about it. Him and Oakley were in the gym, and he was looking like he was gonna come back. It was every day. Weights, pickup games. He was killing.
Walker: It was shit-talking and great basketball. You looked forward to getting up in the morning because you wanted to have bragging rights for that day. The friendships and relationships that were built from that? We spent a lot of time off the court.
Even as a salaried executive and part-owner of the Washington Wizards, Chicago was still home for Michael Jordan.
Having spent 15 years in the Windy City as a player, fans could still sometimes catch Mike flying around town in a sports car, traveling from his historic mansion to the private runs at Hoops Chicago.
While those around town had no idea just what Mike was up to back home, those at the gym were well aware that Mike was all the way back to being Mike.
Crawford: He was just on a whole different level, and you could walk into the gym and see that.
One day, MJ wore an all-yellow Jordan outfit with some yellow Jordans that probably still haven’t come out with a yellow Ferrari outside to match.
Walker: I don’t know if he did that purposely, but Mike was always one of those ones with 20 cars. We all had different cars, but nobody had the Michael Jordan collection.
Mike had the first Ferraris, Porsches, and all that stuff. I don’t think he ever said it was color-coordinated, but it probably seemed that way. I’m not gonna lie; he had all the fancy cars.
Jay-Z and Beyoncé came into town, and they ended up spending the weekend with us. Worldwide Wes brought them to the gym, and they hung out and watched us work out.
Crawford: Uncle Wes was sitting outside of a black truck. When I finally got to him, a window rolled down, and it’s Jay-Z. I literally backed up and said, “Oh, shit!“
Walker: Mike would have them back at the house, and we’d have a little cookout. Since 2001, Jay-Z kept Michael Jordan’s name in a verse. I think it’s because they built a relationship after that.
Mike was more of a people person then. He felt very comfortable at the time. He wasn’t walking around with security guards.
Crawford: His restaurant was next door, and he’d walk with no security. People would drive by and almost crash, screaming, “There’s MJ!”
I loved other players, but nobody like him. It still doesn’t seem real.
Walker: Those are moments that we’ll remember for the rest of our lives.
Nichols: Once he started the practices and invite-only workouts? You kind of knew.
Be sure to tune in on Wednesday for Part 2 of Boardroom’s deep dive into Michael Jordan’s ascension into the Wizards front office.
Read More:
