The Greatest Story Ever Podcast – #11: Michael Jordan’s First Retirement with John Dempsey

John Dempsey is the News Director for 890 WLS in Chicago, and he’s been interviewing interesting people and covering big news stories for years. Back in 1993, he had a front row seat for Michael Jordan’s first retirement press conference.

John Dempsey is the News Director for 890 WLS in Chicago, and he’s been interviewing interesting people and covering big news stories for years. Back in 1993, he had a front row seat for Michael Jordan’s first retirement press conference.

John Dempsey is the News Director for 890 WLS in Chicago, and he’s been interviewing interesting people and covering big news stories for years. Back in 1993, he had a front row seat for Michael Jordan’s first retirement press conference. It was a moment he got to re-live during the ESPN documentary The Last Dance, when he saw himself center stage in the archival footage. 

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Keith Conrad 0:00

Thanks so much for joining me, john.

John Dempsey 0:02

It's a pleasure to be with you.

Keith Conrad 0:04

Now. So the way I've been doing this podcast is, you know, about half of the guests so far I've had on a, I just asked him to come on because because they're a friend of mine or or whatever, or I think they're an interesting person. And, you know, whatever story they they decide they want to share. That's, you know, it's usually gonna be pretty entertaining. But the other half, you know, I've asked them to be on for very specific thing. So, unfortunately, rather than asking you, john, what's the most interesting thing that's ever happened to you? I roped you into talk about about Michael Jordan because you know, the last dance is everywhere. So I might as well hop on the bandwagon.

John Dempsey 0:48

Sure, sure.

Keith Conrad 0:49

Yeah. And so so I literally reached out to you because you posted on social media. Hey, when you look at this, this this footage of, of Michael Jordan's press conference. When he first retired hey there I am, right?

John Dempsey 1:04

Yes. Well, I am and was a huge Michael Jordan fan. And I grew up in Chicago and I you know, I've been a bulls fan my entire life you know before. Certainly before Jordan came along, Gary Sloane Bob love cat Walker top four Winkle. Bobby wise stigmata, the coach, you know, the bulls of the early 70s. They never quite got there they in 1975. They came within one game of going to the NBA Finals, but they lost a heartbreaking series to the Golden State Warriors in 75. And then so Gordon goes to North Carolina and he leaves school a year early in 84. So in the 84 draft, the bulls draft Jordan and and as As we learned by watching the last dance, you know, it was very easy to get a ticket to a bulls game back then because they were awful. They were horrible. And Jordan just kind of comes in and electrifies the city. You know, I think we remember in the last stance in his second year 8586 he, he broke his foot, ankle or foot. I guess the ankle is part of the foot.

Keith Conrad 2:30

It is Yeah, but but i think i think it was the ankle. Yeah.

John Dempsey 2:34

Okay. So he was out for much of the 8586 season. And then he comes back late in the season, and they're limiting his playing time and he's very upset about that. And there was also the subtext in the show that the bulls that the management wanted the team to lose so that they could get a higher draft pick. And Jordan wanted to, you know, go all out and try to make the playoffs and he ended up that famous game scoring exactly three points against slavery burden, and Boston in. I think it was April of 86. And so Jordan obviously captivated the city and, and eventually won the first three championships. 9192 93 and I in the 93 championship. I was working at wb z radio, the public radio station in Chicago. And, you know, I was I was, not only was I a reporter, I was a news reporter, but I wasn't I wasn't really a sports reporter, but we didn't have a sports reporter. So, back then the bulls were news and I certainly did a lot of reporting on the bulls. And then in October of 93, as we learned, Jordan hastily decides to retire from basketball and I attended the news conference, which I can tell you about, but I do. I did remember that there was a photo in the Chicago Tribune, a wide shot of the room of all the reporters and cameras. And there I was right in the middle of the room. And I I remember asking the trivium photographer if I could get a copy of that sent it to me and I framed it and I have it somewhere in storage somewhere but so that on the most recent done the episode where Jordan retired of the last dance, I was anxiously looking forward to that scene to see if I would spot myself and sure enough, when the camera pan the room and saw all the reporters there I was, so I decided to since we're in the age of, you know, but we off to publicize ourselves, right? Yeah. And humblebrag you know, I decided to whip out my iPhone and I recorded that short video of me at the Jordan news conference. And I posted it on Facebook.

Keith Conrad 5:00

So, now I was, it was it was 93. So I would have been 11 at the time. So like I do very clearly remember, like all that going on, but I think, you know, the details are, are somewhat hazy, like you describe it as you know, I hastily, you know, planned retirement. Right. Like, as when you were going into that press conference. Did you know that it was it was Michael Jordan announcing his retirement or the bowl? He was being coy about it?

John Dempsey 5:34

No, that was the reason. You know, when Jordan as we later discovered after the retirement, he tried playing baseball, right. And he was in Alabama where I know you spent a lot of time in Alabama growing up with the replay for the Birmingham barons,

Keith Conrad 5:53

right when he was when he was playing. We actually saw him play twice when the Birmingham barons came out to play the Huntsville stars And that was that was literally the only time that stadium there in Huntsville, Joe Davis stadium was ever full.

John Dempsey 6:08

Wow. Wow. And so you were probably about 12

Keith Conrad 6:12

Yeah, as I was 12 at the time, and I don't remember his exact stats for the day, but I can tell you he didn't do anything. Like he didn't do any. Like the first game. First game. The barons came to town he he did start and I believe he was the centerfielder but but he didn't do anything in the game. And then the second time the the barons came into town, he actually didn't start so you had a lot of people who like the whole game were like, so when is Jordan gonna show up? And finally they're, they brought him in as a pinch hitter, which I don't have anything to back this up on, but I would assume that they probably had to do just about every game, wouldn't you think? Yep. That Yeah. You know, the stadium is packed. Everybody's there to see Michael Jordan so he probably has to come in at some point.

John Dempsey 7:01

Right, right. And I also found it interesting on the last dance. To hear Jerry Reinsdorf say. I think he implied that. Was that a double A? Are we talking about a double it? Yeah,

Keith Conrad 7:13

it was. It was. Yeah, the double A Birmingham barons.

John Dempsey 7:17

So the implication was that Jordan wasn't good enough to be playing double A. But if they had had him at a lower rung, that team wouldn't have had the ability to accommodate all the media. That would be games. So because of that, they put him in double A is that is that how you took that? I don't know if you saw that on the last dance.

Keith Conrad 7:42

I didn't, and the I believe he was 31 at the time. So he was he was old to be a double A. So yeah, you know that. He may have hit 300 if they had sent him to single a but I don't think right And I don't think it would have heard much. And I do know that there was a story that came out that the Oakland A's offered him a major league deal and said, we'll put you on the big league team right now. You don't have to go to the minors. And he, he turned it down.

Wow. Well, so, so backing up. So you were asking me if I was surprised that then I knew going into that news conference in October of 93, that Jordan would be announcing his retirement. So as I mentioned, you know, he played for the Birmingham parents, who were an affiliate of the White Sox. And Jerry Reinsdorf owns the White Sox and on the bowls. So there was a playoff game in the in October of 93, against the Blue Jays and Jordan threw out the game and he's up in Jerry Reinsdorf's box. And then this rumor starts circulating through the crowd. It started with the media. It might have been Jim Gray, who I think was with NBC at the time. Or maybe Pat O'Brien, who I think was with CBS. I don't don't quote me on that. But the it began leaking out that Jordan was going to retire the next day. And then you can see on the last dance pedal Bryan cuts in and says, we've just learned as well. The Bulls have called a news conference for tomorrow morning at the virtual center in Deerfield, and that Jordan is going to be retiring from basketball. So, the answer to your question, yes, I knew when I went up to Deerfield, that this would be the Jordan retirement announcement. I was not prepared for the scene when I got there, but I knew going into it that that's what

and over the years, a conspiracy theory has emerged that you know, that Basically Jordan was was suspended and that's why he that's why he left to play play baseball. Now, I've never bought that for the reason that if you if you suspend the guy, but don't actually say you're suspending him, you're not really suspending him. So what's the point in suspending him? So I've never bought that but have you ever put any stock into that theory?

John Dempsey 10:24

I've never I've never put any stock into that theory. Obviously Jordans like to gamble. And he was a high stakes gambler. He's very, very competitive as we as we see in the in the documentary he's pitching quarters with the security guys in the clubhouse, taking that almost as seriously as he would an NBA game. And I've heard the same thing about him when it comes to golf or ping pong or anything. He is enormously competitive does not like to lose He's got all the money in the world. So yeah, I could believe that he was and perhaps is a high stakes gambler. But gambling is not. It's not illegal. Although back then I guess it was only illegal in Vegas. But at any rate, as we learned from Pete Rose, the only time that it really causes a problem if is if you're betting on your own team. And I don't think anyone who ever saw Michael Jordan play and saw this, the things that he did on the on the basketball court would ever think, oh, he took a bribe to fix this game. Let's investigate that. There's no evidence of that. And to me, that would be the only thing that would be wrong about him. Gambling would be if he had bet on the bowls or something like that. And I don't think there's any evidence of that and I think you're exactly right. If David Stern is going to suspend him, what's the point of not announcing the suspension? Right? You know, and the fact that he quit baseball at around the time when they wanted replacement players because of the labor dispute was still going on. And he, he didn't want to participate in that. And it was probably a good excuse for him to give up. Baseball because we know he wasn't really gonna. I know Jerry Reinsdorf said he might have made it to the major leagues. I don't know if that.

Keith Conrad 12:37

I think Jordan was a good enough athlete, and you know, to your point about his competitiveness, that if let's say about the time that he hurt his foot, he was so disgusted with the bolts that he decided, you know what, forget this basketball thing I'm going to go to, I'm going to go try try baseball. And he did it like when he was say 20 Five or younger than that, then he may have, you know, I I actually probably because of his competitiveness and the fact that he is such a great athlete, he probably would have made it to the to the big leagues. I don't know that he would have been a superstar player, but I think he would have made it is the fact that he was 31 and trying to play in, in in double A, that that was, that was a bit of a problem for him.

John Dempsey 13:25

Yeah. And and and as we learned in the documentary, they were throwing and fastballs early on, and he had like a 13 game hitting streak. And then they began throwing him curveballs and then he couldn't hit the ball at all. Do you know why they only throwing fast balls at the beginning? Was it because he was Michael Jordan and they didn't want to go to too hard on him.

Keith Conrad 13:48

Well, no, I I actually, I think it may have if that's true and I and I've never I've never heard one way or the other on that. That that's the first I've ever I've ever heard of it. If they We're throwing in fast balls, I think it might have actually been the opposite, that you've got a bunch of, you know, double A pitchers who are like, Hey, this is Michael Jordan, I bet I can throw my fastball by him. So maybe it's actually them being a little bit more competitive and saying, you know, I'm, he can't catch up to my fastball so I'm gonna I'm gonna throw it by him. I think that that may have factored into it if he if he did. Yeah. By the way, an interesting sort of side thing on Michael Jordan's time playing for the Birmingham barons. I don't know if this was big news here in Chicago is it wasn't Alabama at the time. But Jordan got there and saw the bus that the Birmingham barons were driving around in and he decided this wouldn't do and actually bought them a bus like for the team. And when I left Alabama after college in 2005, the last time I Went to Huntsville stars game. They were actually still driving that bus because because one of the one of the last kids I went to in Huntsville what they were actually coincidentally playing the Birmingham barons. And, and it was still the bus because the bus actually had like a big 45 on the front. Because Yeah, it isn't being competitive. He had a bit of an ego so he had hit 45 put on the on the bus there we're still driving it. And I was there with with a friend of mine and the bus driver let us like peek in and take a look and and really it was just a normal bus. It wasn't there wasn't anything special about it. But I thought it

John Dempsey 15:40

I heard that but I forgot.

Keith Conrad 15:42

Yeah, that Jordan was literally like, No, I'm not driving around in this thing.

John Dempsey 15:47

Yeah. Wow.

Keith Conrad 15:49

I did the really sad thing about that is the owner of the Birmingham barons, I've met him he could have afforded to buy a bus on his own and he just didn't

So, you know, Jordan, ultimately, he wins the game against the monstars with with Bugs Bunny, and he decides to come back to, to basketball. And, you know, serve the rest is history. Right. Ultimately, ultimately he came back again. Do you think that was just his competitiveness? Or was he bored or a little bit of a little bit of everything

John Dempsey 16:30

you're talking about after he left the polls in 98? After the final three seats? Yeah. And when they when he came back with a Washington, yeah, the Washington Wizards. I think it was probably Yeah, boredom and thinking that, you know, I'm Michael Jordan, if anyone can do this, I can. But I wasn't happy to see him. Come back because he wasn't the same. Jordan, certainly. But I just think to your point, it's his competitiveness. And I think those are the factors that fueled him coming back again. And we've all seen athletes stay around too long. I know you're too young to remember Willie Mays, but when I was about 11 1112 years old, he was playing for the New York Mets. And he was simply awful. But you know, Willie Mays is arguably the greatest baseball player ever. And so there have been a lot of players that have stayed around too long. And then there are others that retire when they're at the top like Jim Brown in football. So but George, George, I think you're right. He was so competitive that he felt that he still has something to contribute and he wanted to play again.

Keith Conrad 17:56

Normally I would ask, you know if there's any important life lessons you learned, From from your experience, but basically the the biggest one would be keep an eye on documentaries because you may show up in them.

John Dempsey 18:10

Yes, exactly. Exactly. Can I just say one other thing about about? And this, what I'm about to say is not apropos to me being in the Jordan documentary, but I have been in the radio. And I did five years of television, but mostly my career has been radio. So I've been doing it now for it'll be 38 years this September. I think I graduated college in August of 82. And I began working right away in, in radio. So I've been a reporter for many, many years. And I always keep I always had a knack for in what they call the the gangbang where reporters are huddling around somebody interviewing them putting their microphones in the person's faces. I always had a knack for that. Standing in front of the person being interviewed, but standing to their side, a because I didn't want to block out any of the TV cameras, but b i just thought it would be easier to get close to them and, and get a good mic position. And so, over the years, there are many, many newspaper photos and a lot of TV footage of me standing to the side of some public figure holding my microphone. So I, I pride myself, Keith, when I look back at my career, I kind of pride myself on that ability. I'm kind of kind of like Where's Waldo? First myself into the shot. So that's why when I saw myself on class dance, I was so proud of myself.

Keith Conrad 19:46

So it's Where's Waldo of Chicago news of the past, you know, past couple decades.

John Dempsey 19:54

Exactly, exactly.

Keith Conrad 19:55

Where is John Dempsey.

John Dempsey 19:57

Thank you, Keith.

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