The Many Iterations of Michael Bloomberg, C.E.O., Mayor, and Presidential Hopeful

Summary

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The Many Iterations of Michael Bloomberg: C.E.O., Mayor, and Presidential Hopeful

The Political Scene | The New Yorker — March 2, 2020
Host: David Remnick
Guests: Andrea Bernstein (WNYC), Eleanor Randolph (author, The Many Lives of Michael Bloomberg)

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Episode Overview

This episode explores the multifaceted life and career of Michael Bloomberg—his evolution from billionaire C.E.O. to three-term New York City mayor to unprecedented Democratic presidential candidate. David Remnick leads a conversation with Andrea Bernstein (Bloomberg’s longtime mayoral chronicler) and Eleanor Randolph (author of his recent biography), dissecting Bloomberg’s power, policies, contradictions, and his wielding of immense personal wealth in politics.

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Key Discussion Points & Insights

Bloomberg’s Decision to Enter Presidential Race

• Bloomberg’s initial reluctance, citing his age and distaste for “apology tours.”
• (03:12) Andrea Bernstein recalls:

  “First of all, he said he didn’t want to go on an apology tour... By the time Ronald Reagan was leaving office, he was gaga.”

• Despite turning 78, friends and personal conviction pushed Bloomberg to run, with Bloomberg using his characteristic humor to downplay age concerns:

  “He once said to me that when he went to the doctor, the doctor said, 'you're going to die, but not of anything you have now.'” (03:47, Andrea Bernstein)

The Bloomberg Campaign Machine

• Bloomberg’s presidential run is described as uniquely “plutocratic”—entirely self-financed and reliant on a massive, coast-to-coast ad buy.

  “Michael Bloomberg is running an unprecedented, unusual and decidedly plutocratic campaign for the Democratic nomination for President… a self-financed coast to coast barrage of TV commercials worth hundreds of millions of dollars.” (01:53, David Remnick)

• Comparison to 2001-2013 mayoral campaigns, which shattered spending records for NYC races.

Buying Influence in Politics

• (05:10) Eleanor Randolph:

  “He spent over $70 million the first time he ran for mayor… had Bloomberg not spent $70 million, I think there is no question that he would have even been a contender.”

• Bloomberg’s philanthropy blurred the lines between generosity and strategic influence:

  “He gave money away to many of the charities in New York City. And some of those people really helped him out in 2008 when he wanted to run again in 2009… He clearly expects people to give back or support him.” (10:44, Andrea Bernstein)

• Randolph notes that “nobody gave to Bloomberg. He gave to people with the expectation that... it would enhance his power. And frequently it did.” (11:28)

On Obama, Sanders, and Democratic Unity

• Bloomberg’s campaign: heavy association with Obama in ads, despite “incredible contempt for Barack Obama as a politician in many ways” (06:10, David Remnick).
• Uncertainty over whether Bloomberg would financially support Sanders, should he win the nomination (07:19).

Stop and Frisk: Legacy and Contrition

• Stop and Frisk is cast as Bloomberg’s greatest mayoral failure; both guests agree criticism was ample during the policy’s implementation:

  “They were so busy focused on the guns that they didn’t see what was happening to the human beings. And it took the courts to declare that it was unconstitutional. And it took Bloomberg a very long time to realize that it was wrong.” (08:46, Andrea Bernstein)

• Bloomberg’s apology seen by both guests as too late and insufficiently empathetic. Randolph cites 120,000 stops of middle school boys:

  “It was very much a criticized policy at the time. And Bloomberg was asked a lot about it.” (09:30, Eleanor Randolph)

Money and Power: Corruption or Just Influence?

• Remnick presses:

  “Do you see that as a form of corruption?” (11:53)

• Randolph:

  “I see that as a form of excessive use of money and power in politics… it stifled people who might have spoken out.” (11:56)

• Comparison to Trump’s transactional style—Bloomberg’s philanthropy is "not pay-for-play" but grants vast backstage influence.

Why Does Bloomberg Want to Be President?

• Bernstein: “He would love to run the country… he talks about himself as a manager, a decider, a person who likes to make decisions.” (14:30)
• Bloomberg’s management ethos viewed as ideological in itself—offering orderly, efficient leadership, but unlikely to upend the status quo.

Gender, Work Culture, and Controversy

• Remnick: “Is he a misogynist?” (16:41)
• Both guests acknowledge Bloomberg emerged from a Wall Street culture steeped in sexism.

  “He began to realize that some of the best people he had working for him were women.” (17:30, Andrea Bernstein)

• However, the presence of NDAs and insensitive remarks, occasionally spontaneous and regrettable, still mar his record.

  “He made a couple of really stupid remarks when he was mayor… one of the reasons he was so stiff as a speaker was that he was trying to resist saying some really smart ass remarks.” (18:24, Andrea Bernstein)

Assessing Bloomberg’s Legacy as Mayor

• Randolph: “I think he was a good mayor… the anti-smoking, the 311, the Roosevelt Island school. At least in the beginning he took over the school system and his purpose was to try to improve the education for kids who generally went to schools that just, you know, sort of waved them through at the very, very best.” (18:59)
• Bernstein provides nuance:

  “He was incredibly complicated... everything with Bloomberg, there’s a countervailing thing,” noting achievements (bike lanes, education reform, public health) often dovetailed with pro-business or elite-oriented goals. (20:15)

• Gentrification and housing prices seen as negatives; Bloomberg’s embrace of international billionaires “makes life difficult for ordinary people in New York City who want to buy housing.” (20:55, Andrea Bernstein)

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Notable Quotes & Memorable Moments

• On campaign spending:

  “It was so off the scale... had Bloomberg not spent $70 million, I think there is no question that he would have even been a contender.” — Eleanor Randolph (05:10)

• On philanthropy as soft power:

  “He gave to people with the expectation that it would enhance his power. And frequently it did.” — Eleanor Randolph (11:28)

• On Stop and Frisk:

  “That is the big hole in his legacy. And so he still has to answer for it time after time.” — Andrea Bernstein (10:17)

• On management as ideology:

  “That’s meant to sound anti-ideological, but isn’t it itself a form of ideology, in other words, that the existing order is exactly as it should be and I’ll just run it?” — David Remnick (15:47)

• On Bloomberg’s complexity:

  “Everything with Bloomberg, there’s a countervailing thing. So something benefits somebody. It also might benefit him. It also might benefit billionaires from Russia… it’s this complicated set of things.” — Andrea Bernstein (20:15)

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Timestamps for Key Segments

• Bloomberg’s entry/reluctance to run: 03:00–04:10
• Campaign spending and 2001 race: 05:00–06:00
• Relationship with Obama and Sanders: 06:10–07:40
• Stop and Frisk analysis: 08:40–10:37
• Impact of philanthropy: 10:37–11:53
• Bloomberg vs. Trump comparison: 12:19–13:57
• Bloomburg’s presidential aims and management style: 14:30–16:15
• Discussion of misogyny, NDAs, and culture: 16:41–18:24
• Mayoral legacy, gentrification, and nuance: 18:59–21:12

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Final Thoughts

This episode offers a comprehensive, nuanced analysis of Michael Bloomberg’s evolution as a public figure and politician, wrestling with the contradictions in his application of immense wealth, managerial philosophy, approach to race and policing, relationships with women, and his ultimate ambitions. Both guests suggest Bloomberg is neither hero nor villain; his legacy, and his foray into presidential politics, is as complex as the city he once led.

Transcript

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[Andrea Bernstein]

I'm Dorothy Wickenden. On today's Politics and More podcast, a conversation about Mike Bloomberg. David Remnick will talk with Andrea Bernstein, who who covered Bloomberg's mayoral administrations for wnyc, and Eleanor Randolph, the author of the biography the Many Lives of Michael Bloomberg.

[Michael Bloomberg]

I think we have two questions to face tonight. One is who can beat Donald Trump? And number two, who can do the job if they get into the White House? And I would argue that I am the candidate that can do exactly both of those things.

[David Remnick]

Michael Bloomberg is running an unprecedented, unusual and decidedly plutocratic campaign for the Democratic nomination for President. Until recently, the former New York Mayor's campaign was one gigantic ad buy a self financed coast to coast barrage of TV commercials worth hundreds of millions of dollars. He was barely a presence on the stump and yet he was climbing in the polls. But when Bloomberg finally went public live at a debate in Las Vegas, he it was as if someone had ripped back the curtain on the wizard of Oz.

[Michael Bloomberg]

We have a very few non disclosure agreements. How many? Let me finish.

[Andrea Bernstein]

How many is there?

[Michael Bloomberg]

None of them accused me of doing anything other than maybe they didn't like the joke I told. And let me just put. And let me put. There's a agreement.

[David Remnick]

Eleanor Randolph is the author of a biography of the former mayor called the Many Lives of Michael Bloomberg. And Andrea Bernstein watched Michael Bloomberg's approach to governing right up close. She covered Bloomberg's mayoral terms, all three of them, for wnyc. And I caught up with them both earlier this week. Eleanor, you finished writing a biography of Michael Bloomberg in June of 2019, right? Just at the very moment when he decided not to run for president. That's right. What was his thinking then?

[Andrea Bernstein]

First of all, he said he didn't want to go on an apology tour. You know, he wasn't gonna apologize. And he also mentioned the. By the time Ronald Reagan was leaving office, he was gaga.

[David Remnick]

Meaning his age wasn't there either. He's now 78 years old.

[Andrea Bernstein]

That's right. So he had convinced himself that it was too late.

[David Remnick]

And so all of a sudden he starts thinking what to convince himself to run for president. I'm no longer going to be 78. I mean, biology is going to reverse itself.

[Andrea Bernstein]

He once said to me that when he went to the doctor, the doctor said, you're going to die, but not of anything you have now. And so that was his way of saying he was in good physical shape. And so he told his friends that people were calling him all the time and telling him he needed to get in.

[David Remnick]

You've covered Bloomberg for years when he was Mayer. You've certainly watched him very carefully ever since. Isn't that the nature of the Bloomberg universe? People tell me things that I kind of want to hear.

[Eleanor Randolph]

Well, I mean, I think, yes, mostly. Although he is somebody that is better than most at discarding unwelcome facts. By discarding, I mean, considering things and changing course, I think it's very hard. Once you've been the mayor of New York City and you're the star of the show every day and the press always wants to talk to you to say goodbye. So anything that argues for you to re enter that political stage, you are going to give a special weight towards.

[David Remnick]

I think no matter how you feel about Michael Bloomberg's politics or his record as mayor for three terms, that you would have to acknowledge that he bought that office. Is that. Am I wrong to say this?

[Eleanor Randolph]

He spent over $70 million the first time he ran for mayor, which was shocking. I mean, I think Giuliani spent somewhere in the area of 10 million. So that was the scale. It was so off the scale. Now, a lot of things happened that election year that pushed the mayoralty towards Bloomberg. I think obviously the most significant thing that happened was 9 11, which enhanced the stature of Rudy Giuliani, so that when he endorsed Bloomb, it really meant something. But had Bloomberg not spent $70 million, I think there is no question that he would have even been a contender. He spent $100 million the second time around and an equal amount the third time around.

[David Remnick]

Eleanor Bloomberg has now spent hundreds of millions of dollars, mainly on television ads, but also on a web strategy and staff and much else. One of the most famous ads that he's put on is to show how deeply he's associated with Barack Obama. I have heard from the horse's mouth, from Bloomberg in private that he had incredible contempt for Barack Obama as a politician in many ways. Who's he kidding?

[Andrea Bernstein]

You know, one of the things you have to say is that this is a guy he's worth now, I'm not Sure exactly, probably $61 billion, $64 billion.

[David Remnick]

Although yesterday was a rough day at the stock market.

[Andrea Bernstein]

Yeah. So it may be closer to 60 billion dol. So I mean, he wants to use that money to change the world. And what you're seeing right now is his own campaign, but mainly he's trying to get rid of Trump. And most of those ads, if you watch them carefully, they're designed to soften Trump up and to make sure that whoever the Democratic nominee is, that person will have an easier go.

[David Remnick]

But he's not making it easier, particularly, particularly on Bernie Sanders. He's attacking Sanders pretty hard. Do you think if Sanders prevails in the primary that Mike Bloomberg will go on spending many, many millions of dollars to support Sanders against Trump?

[Andrea Bernstein]

I don't know. How many, many millions do you think he might recede? My suspicion is that if he's not the nominee and that Bernie is the nominee, he will start focusing on the Senate. Right now they are talking about how worried they are about whether Bernie will cause problems down ballot Michael Bloomberg, and.

[David Remnick]

I see this in your biography. There's a struggle between the good Michael Bloomberg, which you can describe, and let's just say the far less good Michael Bloomberg and comments about women stop and frisk. All kinds of policy decisions that were really demonstrably off base or wrong, but overall a personality that, let's just say, not the most generous in the world. How did you come down on him when you finished this project?

[Andrea Bernstein]

Well, you know, people often ask me if I like him and I have to say That I see this guy improving with age. I mean, I would not have liked him when he was on Wall street, you know, at Salomon Brothers. He was a total jerk back then. And he seems to learn from his own mistakes. I think Stop and Frisk is a perfect example of it. He and the police commissioner, Ray Kelly, decided that they really needed to get these guns off the streets.

[David Remnick]

But even at the time, there was considerable criticism. This was abusive of people, particularly black and brown people.

[Andrea Bernstein]

Well, that's what I was going to say. They sort of lost the understanding of what was happening on the streets. They were so busy focused on the guns that they didn't see what was happening to the human beings. And it took the courts to declare that it was unconstitutional. And it took Bloomberg a very long time to realize that it was wrong. And his apology right before he ran, a lot of people felt it was too little and too late.

[David Remnick]

Did you?

[Andrea Bernstein]

I felt that he needed more understanding or to state more about how people were damaged by the Stop and Frisk.

[Eleanor Randolph]

I think it was very apparent while it was going on. And I mean, not only were there the lawsuits, but I mean, WNYC did a whole bunch of stories about Stop and Frisk and the numbers were staggering. One story that I just went back and looked at recently showed that there were 120,000 of stop and Frisk of middle school aged boys. It was very much a criticized policy at the time. And Bloomberg was asked a lot about it.

[Andrea Bernstein]

Oh, right. But he kept saying the same thing, which was that if they stopped this version of Stop and Frisk, that the crime rate would go up. What he has never explained very well is why they decided to just sort of let the police force go out and stop every kid who had a Coke bottle in his pocket. And it was, you know, this. If you want to look at Bloomberg's years as mayor, that is the big hole in his legacy. And so he still has to answer for it time after time.

[David Remnick]

How did he use his money, his personal fortune, to neutralize political opposition in the city?

[Andrea Bernstein]

Well, he used it. He gave money away to many of the charities in New York City. And some of those people really helped him out in 2008 when he wanted to run again in 2009. And so as he gives out money, he clearly expects people to give back or support him.

[Eleanor Randolph]

Absolutely. I mean, I would hear that too. Cultural institutions. I mean, you just have to be a person alive and attending a museum or a theater in New York City at any time. And the name Bloomberg, Bloomberg, Philanthropies is there. He's given enormous amounts of money to environment, environmental organizations. There's a lot of people who don't need to be told and didn't need to be told, but understood that one of their major funders was also the mayor of New York City. And this was, I mean, sort of with Bloomberg, it was topsy turvy, as someone who sort of covered campaign finance and corruption would always sort of trace the money upwards. So look at who was giving. Nobody gave to Bloomberg. He gave two people with the expectation that. That it would enhance his power. And frequently it did.

[David Remnick]

Do you see that as a form of corruption?

[Eleanor Randolph]

I see that as a form of excessive use of money and power in politics. And it without a doubt, stifled people who might have spoken out, who might have had something to say but were afraid to. And I think that is the. I mean, I think it's not like, you know, he's not in any way a sort of transactional businessman like Trump. Where. Trump. That's what I want to get to.

[David Remnick]

You've written this excellent book on the Trump family, the Kushners and the Use of Money. How do you compare Trump to Bloomberg?

[Eleanor Randolph]

So it's interesting because obviously they are both New York very rich men, but Trump really came from this sort of oligarchic model of government where he understood, and his father before him, that to get things out of New York City government, they would pay. So they would support a politician through campaign contributions, through hiring people, through a variety of methods, and they would expect very directly that they would get something in return. People would say to me, official after official, very senior levels, I know absolutely why he gave me that, because he called me and he told me and he said, I gave you $20,000. Where is my permit? Where is my tax package?

[Andrea Bernstein]

And.

[Eleanor Randolph]

And Bloomberg is not that way. He is not that kind of direct transactional politician who believes you pay somebody and you get something directly. And yet he, while he was mayor, gave many, many hundreds of thousands of dollars to the Republican Party. He was a Republican. He gave many, I think, millions of dollars to the Republican National Committee. All of the money that he gave to philanthropies and charities were a way of doing good in the world. Sure. But they were also a way of making him more powerful as mayor and giving him an advantage that someone without all those billions would not have been able to.

[David Remnick]

There's another point of comparison. When Trump initially declared for the presidency, it was thought, and I think it's pretty confirmed, that really what he was aiming to do was enhance the brand that he'd run for president. He'd get endless, endless free media. His speaking fees would go through the roof. Maybe he'd start a television network. Something good would happen to him commercially. But he'd lose.

[Andrea Bernstein]

Right.

[David Remnick]

And this freakish thing happened. He won, but he set out wanting a certain thing. What does Bloomberg want by running?

[Andrea Bernstein]

You know, I actually think that he would love to be president. He would love to run the country. He's said that he told his friends in college that that goes way, way back. And, you know, he told his friends.

[David Remnick]

In college that he'd like to be president.

[Andrea Bernstein]

Yep, he did. You know, and I think one of the things you'd see if he were elected president, you'd see a manager take over the White House. He talks about himself as a manager, a decider, a person who likes to make decisions. And one of the things he says very often is that the first decision you make if you're running a new corporation is you find the best people you can hire. People who are smarter than you are usually.

[David Remnick]

Don't they all say that?

[Andrea Bernstein]

No, they don't.

[Eleanor Randolph]

For him, it's really. I mean, I think first of all, he spends limitless amounts of money on staff and does attract talented staff. And he does. I mean, he ran on. When he ran for mayor the first time, it was the same thing. He said, I'm going to manage this city well. And I thought, well, what does that mean?

[Andrea Bernstein]

I know it's not very sexy, but it's actually.

[Eleanor Randolph]

I mean, I actually think it did mean something. I actually think that sort of after the tumult.

[David Remnick]

Forgive me, but that's meant to sound anti ideological, but isn't it itself a form of ideology, in other words, that the existing order is exactly as it should be and I'll just run it?

[Andrea Bernstein]

Well, no, I mean, what. Well, what I think he's saying is that if he took over the White. I mean, you look at how the White House is run now and, you know, there's a.

[David Remnick]

You don't think it's run well.

[Andrea Bernstein]

I think I can run it better.

[David Remnick]

Trump called it a humming machine.

[Andrea Bernstein]

Oh, yeah, right, of course. But I think the other thing about how he would be president and how different it would be, it would just be quieter, you know, you would just. You wouldn't. He was better, I think, than Trump about seeing the press, but, you know, he still would have to answer all the tough questions.

[David Remnick]

Is he a misogynist, Andrew?

[Eleanor Randolph]

Well, I don't. I mean, I would say that he has largely empowered women in his career and as a political figure. I mean it was a very different time then and it was interesting because I was sort of going back and looking at the coverage of Bloomberg and it was still very much a man's world, sort of the who had power, who had say who the chief political political reporters were at the time. So it's hard to sort of judge how he would be received if he behaved the way he behaved as mayor in today's standards.

[David Remnick]

Eleanor, the question of women and misogyny, which came up certainly in the first debate and has come up before and you cover quite well in your book. How do you come down on that question with him?

[Andrea Bernstein]

First of all, he came from the culture of Wall street which was very anti female and his company kind of started out with that culture, some of that culture and you could see over the years that he began to move away from that. And if you look at the passage of a person's life, which you do when you start writing a biography, you know, they either get better and learn or they don't. And one of the things that happened to him is that he began to realize that some of the best people he had working for him were women.

[David Remnick]

But it coexists with the history of non disclosure agreements with remarks that you quote copiously in your book that are it's kind of late in the day for them to be excused in any serious way, aren't they?

[Andrea Bernstein]

He made a couple of really stupid remarks when he was mayor, you know, and I don't think he could resist. There was a I have often thought that one of the reasons he was so stiff as a speaker was that he was trying to resist saying some really smart ass remarks.

[Eleanor Randolph]

You know, he used to be so formal in city hall press conferences. I mean years after he knew everybody's first name he would be yes, miss like he was meeting you for the first time.

[Andrea Bernstein]

I know neither of you think he's.

[David Remnick]

I don't want to read this wrong. You were somewhat forgiving about this but.

[Andrea Bernstein]

Well look, I think he was a good mayor. I mean I don't like everything he did and but you know, the anti smoking, the 311, the Roosevelt Island School and in fact I would even argue that at least in the beginning he took over the school system and his purpose was to try to improve the education for kids who generally went to schools that just, you know, sort of waved them through at the very, very best. So I always felt that if on balance he was a good Mayor Andrea.

[Eleanor Randolph]

Do you agree, Do I agree that on balance he was a good mayor? Yeah, I think he was incredibly complicated. I think he did many good things, for sure. I don't think I would pass the same judgment as Eleanor has because I think that so many of the things that he did, even something like bike lanes, which were great and I love and use and wish there were more of, but they were also. And they would say this a way that they were going to attract more international companies. So I feel like.

[Andrea Bernstein]

Well, also. And calm traffic, that was the main thing.

[Eleanor Randolph]

But I mean, I think that there's sort of. There's so many kind of. I think, as Eleanor was saying, everything with Bloomberg, there's a countervailing thing. So something benefits somebody. It also might benefit him. It also might benefit billionaires from Russia. There was one point where in 2013, he gave an exit interview to New York Magazine. He said, yes, let all the Russian billionaires move to New York City. We welcome them. They will pay taxes. Well, that is something that obviously makes life difficult for ordinary people in New York City who want to buy housing. And during Bloomberg's time as mayor, housing prices nearly doubled in parts of Manhattan. So it's this complicated set of things that I would imagine as president that he would be both addressing issues but not making sweeping, fundamental changes.

[David Remnick]

Andrea Bernstein, Eleanor Randall, thanks so much.

[Andrea Bernstein]

Thank you.

[Eleanor Randolph]

Thank you.

[David Remnick]

Eleanor Randolph's book is the Many Lives of Michael Bloomberg. Andrea Bernstein is the author of American the Kushners, the Trumps and the Marriage of Money and Power. And she's the co host of the Trump Inc. Podcast from WNYC and ProPublica.

[Andrea Bernstein]

Foreign.

[David Remnick]

I'm Katie Drummond. I'm Wired's Global Editorial director. I'm Michael Colory, Wired's Director of Consumer Tech and Culture.

[Andrea Bernstein]

And I'm Lauren Good. I'm a senior correspondent at Wired. And our show Uncanny Valley is all about the people, power and influence of Silicon Valley.

[David Remnick]

At Wired, we're constantly reporting on how technology is changing every aspect of our lives. So each week on the show, we get together to talk about one of.

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The biggest stories in tech.

[Andrea Bernstein]

Right?

[David Remnick]

So whether we're talking about privacy, AI, social media, or a major tech figure, we will always explain the Silicon Valley forces behind these stories and how they affect you. Make sure you're following Uncanny Valley in your podcast app of choice so you.

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[Andrea Bernstein]

From prx.