Legal AF Special Report - 12/24/2025

25 Dec 2025 · 29 min · 8 chapters

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In short

David O’Keefe’s protest against Skadden Arps’ reported $100 million “pro bono” deal with the Trump administration, and his lawsuit over his arrest for standing with a sign in New York City’s privately owned public spaces (POPs), which he argues must allow First Amendment speech.

Guests/backgrounds

David O’Keefe, former Manhattan DA prosecutor (Crime Strategies Unit leader 2010–2014; Deputy Trial Division Chief; retired 2020); Karen Friedman Agnifolo, long-time Midas Touch host/colleague.

Key claims

O’Keefe says institutions “folded” (citing Paul Weiss and then Skadden bending the knee). He claims Brookfield Properties, as POP owner/manager, is the “bad actor” because POPs function like public space and must permit speech. He says NYPD officers were poorly advised; charges were dismissed.

Notable examples

He returned 34 times (Apr 1–Oct 27) with changing signs; he was arrested April 2 for trespass, cuffed and taken to precinct; he alleges Skadden security intervened April 4 to avoid another arrest.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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David O'Keefe's Protest Against Skadden

1:40 to 3:56

David O'Keefe recounts his protest against Skadden's actions with the Trump regime.

“When David saw some of these big firms bending the knee and capitulating to the Trump regime like a huge law firm and was a firm that was one of the most prominent in the United States called Skadden and Arps.”

Privately Owned Public Spaces Explained

3:56 to 5:01

Understanding privately owned public spaces in New York City.

“Allied Universal, Brookfield Properties, the New York City police officers, James Farrell and Marion Binaca.”

David's Background and Impact

5:01 to 6:12

David's journey and innovative contributions to law enforcement.

“He created a computer program internally before anyone else in the whole country was doing anything remotely like this.”

The Turning Point for O'Keefe

6:12 to 8:00

David discusses the moment he decided to take action against Skadden.

“introduce, bring you into this and thank you so much for joining.”

The Arrest and Continued Protest

8:00 to 14:00

David shares details of his arrest and ongoing commitment to protest.

“You know, for 25 years, I worked at the Manhattan DA's office.”

Advocating for Free Speech Rights

14:00 to 20:20

Learn about the importance of upholding free speech in public spaces and the author's personal experience advocating for it.

“Let's talk about the lawsuit that was filed.”

Resilience Against Authoritarianism

20:20 to 25:34

Explore the importance of individual resilience and public activism in the face of authoritarian challenges.

“It's just kind of a final takeaway of this experience and what you suggest for, you know, anyone else out there who's listening to this or watching this.”

Resilience Against Authoritarianism

25:55 to 27:16

Explore the importance of individual resilience and public activism in the face of authoritarian challenges.

“Become a subscriber to our sub stack at MidasPlus.com.”
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Transcript

Automatic transcript. May contain errors.

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1:19Ben Meiselas:So I want to introduce you in just a moment to someone by the name of David O 'Keefe. David O 'Keefe was formerly a prosecutor in the Manhattan District Attorney's Office. And during his tenure, he led the Crime Strategies Unit from 2010 to 2014 and was a Deputy Trial Division Chief before retiring in 2020. When David saw some of these big firms bending the knee and capitulating to the Trump regime like a huge law firm and was a firm that was one of the most prominent in the United States called Skadden and Arps. When they entered into a$100 million deal with the Trump regime, David said enough is enough.

2:04Ben Meiselas:Enough is enough. And even though David was retired, he went out there to the location where Skadden's office was. He went there by himself, one man, one sign. And the sign said the following, hey, Skadden, I found your spine in the trash lying next to your values. Trump's$100 million lab dog. And again, this was a former top prosecutor in the Manhattan District Attorney's Office just said, you know what? I don't care if anyone else is going to be there. I'm going to show up with my sign because this pissed me off and I'm going to do something about it. It's what we always tell you, the might is mighty, that you should do something about it.

2:47Ben Meiselas:Except David O 'Keefe, not surprisingly, or perhaps surprisingly to you, but in this country that we currently live in right now, he was arrested and he was charged, at least for a short period of time, with trespass for being in this area that appeared to be a public area. It turns out that if you actually delve into what's going on in New York City, There are hundreds of spaces that are privately owned, but that because of an agreement between the property owner and New York City are technically open to the public and indistinguishable from public sidewalks, plazas or parks. These spaces where commuters walk to work, tourists gather, shoppers stroll and where people sometimes hold protests, they're called privately owned public spaces.

3:36Ben Meiselas:You wouldn't be able to really even know the difference, whether it's a public space or a privately owned public space. And they constitute over 3.8 million square feet of public space in New York City. So O 'Keefe was charged. He fought it. The charges were eventually dismissed. And now he's brought a lawsuit against the city of New York under its old regime, but it's still being brought right now. Allied Universal, Brookfield Properties, the New York City police officers, James Farrell and Marion Binaca. And I want to talk to David, but to introduce David in a way that I can't and that my intro doesn't do it justice.

4:17Ben Meiselas:I want to bring in Karen Friedman Agnifolo, who you all know has been with Midas Touch since the very beginning. Karen, it's great to see you. And David, It's great to see you. Karen, let me toss it to you. Yeah, David O 'Keefe is a very unique person. He was a prosecutor, a career prosecutor for decades, about almost 30 years, probably more. And David O 'Keefe was a CPA prior to becoming a prosecutor. And he turned his knowledge as a CPA to literally single-handedly drive crime down in New York City. he introduced a concept of data-driven prosecution. Pay attention to where the crime is occurring and who the bad actors are.

5:01He created a computer program internally before anyone else in the whole country was doing anything remotely like this. And Cy Vance, the Manhattan DA, took what David was doing, created this thing called the Crime Strategies Unit, and we saw crime go down. Literally, there was one neighborhood that had, I think it was 14 murders the year before, had zero the year after, after David's targeted prosecution. And in fact, what David created was so successful that we took it on the road and we introduced it to the entire country. And so many prosecutor's offices around the country now have this crime strategies unit that David created.

5:44So David is a genius. He literally transformed how you prosecute crime and what you do at the Manhattan DA's office. He was a valued, trusted colleague, beloved by everybody. And so when we saw this lawsuit and what was going on and what David is doing, I said, we have to pay attention to this because this is real and this is going to prevail because David is the real deal. So David, I want to introduce, introduce, bring you into this and thank you so much for joining. The fact that, you know, David also is kind of a quiet person. He's not the guy who walks around the office telling people what he's doing or bragging.

6:25In fact, he created this entire computer program that I was telling you about basically without telling anybody. We kind of found out about it and we had to beg him to come and take a supervisor, leave his, he was a homicide prosecutor and senior trial counsel. and we literally had to beg him to come and be more like help us put what you're doing in a small scale let's do it for the whole office for the whole for the whole Manhattan for the whole city of New York and for the whole country so so again this is so typical of David to do something quietly independently but completely substantively so David thank you so much for coming and welcome to our show well thanks for inviting me Karen and Ben it's great to be here it's great to talk about this issue because I think it is really important and, you know, something that people can do themselves as well.

7:18Ben Meiselas:So, David, walk us through, if you can, what happened on that day on April 2nd. Had you attended protests before then? Do you have a history of protests? When was it enough where you just said, you know, Scadden, enough is enough? Like, how could, I remember that date because, you know, Scadden, for those who don't know, you know, has one of the most august reputations in in this legal community. They were one of the gold standard law firms that were out there that would always recruit when I was in Georgetown Law and other top law. You know, Scadden was always out there talking about its pro bono, how they help the country, how they do this and that.

7:57Ben Meiselas:So talk to us about, you know, what led to that. And then we'll talk about what happened. You know, for 25 years, I worked at the Manhattan DA's office. And the North Star there was to do justice, to do what is right, as Karen well knows. And when the current administration started attacking the legal system, I thought it'll hold. The institutions will hold because we will do the right thing. Because that's how I was taught. That's my belief. And so when Paul Weiss on March 20th was the first to fold, I thought, you know, this is an aberration and there are other firms that are fighting what's happening with the Trump administration.

8:38And so when Skadden on March 28th actually went to the administration and said, we would like to bend the knee and we will give you$100 million of pro bono services to do as you wish. I thought it's time for someone else to do something. We have to step up because the institutions are not. They are folding. And so it falls to us as lawyers ourselves to say this cannot stand. So I was away when that happened. I came back on March 31st. I went to the store. I put a poster together on March 1st. I went out to Skadden and I stood on the public sidewalk on the north side, actually, of their building.

9:30And with that sign. And it was empowering. was really, it felt good because I was making a statement and people were supportive. A lot of people on their way to work weren't necessarily paying a lot of attention, but it felt like I could actually do something and hold the feet to the fire of the lawyers who were not. So that day though, a security guard came out and said, I was standing on the sidewalk and said to me, you are on private property. You cannot stand here. And I thought, this is absolutely ridiculous. I'm not going anywhere. And told the security guard, no, I'm not moving. And the security guard left.

10:17And I might not have gone back, but I'm holding a sign that says, you are a coward, Skadden. So I felt I needed to return and show that I couldn't be driven off and couldn't be bullied into silence. So I went the next day to the south side of that building, which is in the privately owned public space, which as you described, is privately owned property, but is open to the public. So it's different from straight private property. And as I stood there, that same security guard came up to me and said, you can't be here. This is private property. And I disagreed and said, it's private, they own public space.

10:58And the security guard said, I'm sorry, they don't want that stuff here. You cannot remain here. And so we had a little back and forth. I said, I'm not going anywhere. And he called the police. And about a little over an hour later, two police officers arrived, told me I had to leave. I said, no, I'm allowed to be here. And they put me in cuffs. and took me to the precinct. Yeah, I mean, so just these privately owned public spaces for people who don't live in New York City, these are maintained and owned technically by buildings and private companies, but these are negotiated public spaces. This is something that was created, I think, in the 1960s as a way of making more public spaces available because this is such a dense environment, such a dense urban environment.

11:55And New York wanted to have more public spaces, parks, etc. Many of these look like parks. Many of these, you don't know the difference. And the reason that private properties enter into these is because they can get away with making taller buildings, i.e. making more money through rents and having more valuable property. So they are literally selling parts of what they bought to the city and saying, I'm going to maintain it. I'm going to keep it clean. There's rules that govern it. You have to make it look like you have to have places to sit, et cetera. So these are public spaces, even though they are technically privately owned.

12:34And so you were exercising your first amendment right of free speech. You weren't blocking any sidewalks or any entrances. You weren't disturbing the peace in any way. And the way David is speaking is the way he always speaks. I've actually never seen you raise your voice. So I can imagine that that's exactly what you were doing. You were just standing there. How many days did you go back? Did you go back after your arrest? I did. I've been there 34 times since between April 1st and I just checked October 27th was the last time. You know, part of it was that I didn't want to be intimidated away.

13:10And I think it's just really important that we not forget what is happening.

13:17lives. And it looks like nothing has changed, nothing is moving. And for these law firms, I think that they hope that people will forget what they have done and they can just move on and make their money. So I wanted to stand witness, bear witness about what is happening. So I returned multiple times. And being New York, I didn't want to just fall into the background. if I stand there with the same sign every single time, people will stop seeing me. And so I did a series of signs, about six or seven different signs, that reflected my thoughts about the cowardice exhibited by Skadden. And actually, the great part was the Skadden employees, some lawyers, some non-lawyers, who would stop by and talk to me, who would give me the thumbs up, who would give me a pound, who would give me a smile and say how hard it was to work there and try to maintain their own integrity and values with what the firm has done.

14:19And they appreciated the support. So there were a lot of people who walked by who maybe didn't really know what those signs were referring to, but I wanted to be there for Skadden, for the employees to say, yes, we remember what you've done and we really hope that you will take a stand to the extent that you can and that the managing partners are embarrassed by what they have done and really kind of threw away their oath to uphold the constitution when they settled with the administration.

14:52Ben Meiselas:Let's talk about the lawsuit that was filed. What brought you to the point? I mean, Skadden's not a defendant because technically this is over the wrongful arrest. This was also over the privatization of these public spaces and the developer of that specific space. And so that's why those defendants are mentioned. What are you hoping to accomplish with the lawsuit other than the fact to vindicate a right that you were arrested for advocating your First Amendment rights, of course. You want people to know about this issue in New York and what else do you help to accomplish as well? Well, you know, I think what you said about vindicating that right, I just think it's really important that in our city that we uphold the right of free speech in all of our public spaces.

15:43And whether it's the POPs or something more typically understood to be a public space. on April 1st when the security guard came out and confronted me on the sidewalk he said there had been a woman there the day before protesting and he had told her that she could not remain on the sidewalk and she agreed to move further down the street towards 9th Avenue and I thought gosh you know what was it like for her to be intimidated and not to feel confident enough or know the law well enough to know that she could be there. And so I thought, I am in a position where I am comfortable enough. I have the ability, I have the resources to take this on and vindicate those rights.

16:28You know, in my view, the bad actor here is really Brookfield Properties. Yes, the NYPD did arrest me. The two officers were very poorly advised by their supervisor. They did not reach out to the legal bureau when I asked them to. But Brookfield Property knows better. They were the property owners when Occupy Wall Street happened, when Zuccotti Park was all litigated. They own the Zuccotti Park Pops. And these were all issues that were front and center 12, well, that was 2011, 14 years ago. And so in my view, Brookfield Properties has taken the economic benefits of extra space and millions of dollars of rent, and then just gone their own way and said, we will do what we want to do in these spaces and disregard the law and the Constitution.

17:22They're not a public entity officially, but when they create and agree to maintain those spaces, they step into the shoes really of the city and they have an obligation to allow speech. and it may be speech that they don't like or that their tenants don't like, but it doesn't change the fact that they need to allow it. So I'm really hoping that the lawsuit makes clear ultimately that those spaces are available for public expression, free speech expression, and that Brookfield Properties will either admit they're wrong or be told that they were wrong and change their practice. I mean, Brookfield Properties operates properties everywhere, all over the world, North America, Europe, Latin America, and Asia as well.

18:14And they've been around a long time. They manage, I think, according to public available information, they manage over 1 ,100 assets, over 370 million square feet globally. and I mean this is a huge huge real estate portfolio and business and so it's a big real estate company that you're taking on and you're right they should have known better what do you think Skadden's role in this is do you think that they had that they were calling the shots and calling their managing agent and saying get these get this guy out of here I did on day one and on day two. But on the 4th, on April 4th, I went back to that same Pops and held up my sign and was confronted by three security from Mulligan Security.

19:07Mulligan was then bought by Allied Universal. So that's why Allied is in the suit. And I was told that I had to leave the space. And I was pretty sure I was going to get arrested. And then surprisingly, the head of security for Skadden came down. And he indicated, he said to me that Skadden had heard what had happened, they'd seen that I had just been confronted by the security, and that they were hoping to avoid an arrest, that they opposed the arrest. And ultimately, I think that I was not arrested because of the intervention of Skadden. So I don't know if they decided that they better step in, because this is really bad press for them.

19:55I don't know if they decided to step in because they understood that there was a free speech issue here and that Brookfield Properties was on the wrong side of it. But I do think ultimately that I was not arrested again, at least on April 4th, because the intervention of Skadden. And that surprised me.

20:15Ben Meiselas:Before we go, David, I want our listeners and viewers to kind of hear from you. It's just kind of a final takeaway of this experience and what you suggest for, you know, anyone else out there who's listening to this or watching this. And in this moment, you know, they're feeling obviously concerned and uneased by what this regime is doing. Terrified, psychologically tortured. Pick your word. I think they're all likely. What's interesting is there was that period of time, February, March, where I think lots of people just felt we've lost our country. And then they started to see small acts of resistance building right around that time as well, which turned into bigger acts, which turned into no kings.

21:10Ben Meiselas:And I think if I'm defining 2025 while our institutions bent and broke, the people resiliency, I think, is an attribute that actually surprised this, you know, surprised this regime and its enablers. So what do you want people to take away from this? You know, at one point I was away for maybe two weeks or so from being out there. And then I was back with my poster and someone walked by and just said, you're wasting your time. And about five minutes later, a man walked by and said, yeah, you're back. And my sense was that people need to know that they're not alone in this. So I think many of us are feeling, if not under attack, certainly really concerned about the direction of the country towards authoritarianism.

22:05And so I think that we as individuals can actually make a big difference by showing up. And so I've been out there, as I said, 34 times each time, over one alone. And a number of times people have said to me, but you're just, where's everybody else? And I think that we can say, I can do what I can do and not worry about what others are going to do and show up. So, you know, maybe we can adopt a coward. So retired lawyers can go to each of the nine law firms and say, I'm going to show up and bear witness multiple times. I'm going to lend a spine and just hold people to account and say we are not going to forget.

22:54I think our institutions are really bearing the brunt of this. And so it takes us, the nobodies, the little people to hold them up. And I think that we can do that. And if you can do it once in a year, that's great. If you can do it once a month, that's great. You can do what you can do when you can do it. But it really makes a difference when community sees people and even one individual out there with the viewpoint that they support, that they feel like they're not seeing out there challenging the administration and what's happening.

23:30Ben Meiselas:Karen, I'll let you close it out. And if you have any more questions, but it would be, I think a great idea. Imagine you do an adopt a coward, adopt a coward. You go through, you know, whether it's Scadden or Paul Weiss's website, and you take one of those partners or associates out there. And then the people get to literally, you get one, you get to adopt them. And you know, you, you take care of your little coward. You'll occasionally let them know what they're, you know, I love it. Adopt a coward, like a Chia pet. The coward grows more cowardly by the day. Karen, I'll let you. I know. When he said that, I was like, that's just genius.

24:04Typical David O 'Keefe, brilliant genius. David, I think you perfectly described exactly what the Midas community is. The Midas community is individuals who have come together because they all are looking for a place. We are all looking for a place to come together to do our part and to do our one thing and you just perfectly exemplify exactly what the might is mighty is what we call ourselves and um and going out and doing exactly the thing that person can do and so the fact that you came on here told your story we're going to hopefully lots and lots of people will see it. Others will adopt a coward.

24:49And we are going to make a difference and beat back this authoritarian regime because we have to. And even if it sometimes seems helpless and hopeless, you know, stories like yours, especially this time of year, you know, it's good to always have these kinds of stories so people can have some hope going into the new year and thinking about things that they can do. And thank you for coming on here. It's so inspiring and for just showing your strength and your courage and hopefully inspiring others who will be able to do the same thing or whatever they can do, but something to fight back. Because if we all fight back together, I think we will win, or I know we will win because we have to.

25:35Yeah. Well, thank you for having me on this platform. It's really very much amazing. And And thank you for what you do.

25:42Ben Meiselas:Everybody hit subscribe. Let's get to 6 million subscribers. And David, thank you so much for telling us your story and for showing your courage as well. David O 'Keefe, everybody, thank you. Thank you. Take care. Want to stay plugged in? Become a subscriber to our sub stack at MidasPlus.com. You'll get daily recaps from Ron Filipkowski, ad-free episodes of our podcast, and more exclusive content only available at MidasPlus.com.

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From the publisher

MeidasTouch host Ben Meiselas and Legal AF host Karen Friedman Agnifilo host a special holiday edition Legal AF featuring the inspiring story of retired prosecutors David O’Keefe who protest the behavior of a law firm that capitulated to Trump.

Subscribe to Legal AF Substack: https://substack.com/@legalaf

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