Josh Koskoff on Defying the Odds in High-Profile Trials
Raising the Bar with RebuttalPR

Josh Koskoff on Defying the Odds in High-Profile Trials

  • Season
    1
  • Episode
    9
  • Published Date
    April 16, 2025
  • Episode Duration
    31 Minutes
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In this episode of Raising the Bar with RebuttalPR, host Ray DeLorenzi sits down with Josh Koskoff of Koskoff Koskoff & Bieder in Connecticut. Josh shares his journey from growing up in a family of renowned trial lawyers to taking on some of the most challenging cases in American legal history, including the historic settlement in the Sandy Hook Elementary School shooting litigation against Remington. 

Josh talks about his early exposure to trial law through his father and grandfather, the impact of a difficult medical malpractice case early in his career, and motivation that gave him the confidence to take on monumental cases.   

Tune in for a conversation about taking on powerful interests and the importance of authenticity in the courtroom. 

Learn more about Josh Koskoff and his firm's work at koskoff.com. 

Read the transcript

This transcript of Raising the Bar with RebuttalPR was generated using AI transcription and lightly edited for readability. It may contain errors, and speaker labels are approximate. The audio recording is the authoritative version.

Welcome to Raising the Bar with RebuttalPR, the podcast where we elevate the stories of the plaintiff's bar and dive into the key trends shaping the civil justice system today. I'm your host, Ray DeLorenzi, and in each episode, we'll bring you insightful interviews with leading attorneys, expert perspectives on current legal events, and in-depth discussions on the issues that matter most. Now, let's jump in.

So I got this kind of sense that being a lawyer was really a little bit more of a service-type profession. And a little bit like a gambler and a fighter, really, for people who may never have had one in their corner. And so it's a very idealistic view.

Ray: Hey, everyone. Welcome to a new episode of Raising the Bar with RebuttalPR. I'm your host, Ray DeLorenzi. Today I'm joined by Josh Koskoff of Koskoff, Koskoff & Bieder in Connecticut. Josh almost needs no introduction. He has worked on some of the most society-changing cases of the last several decades, most notably the Sandy Hook shooting, which we'll get into a little bit later. But thank you, Josh, for joining the podcast today.

Josh: Thank you, Ray. I'm thrilled to be here.

Ray: So, Josh, I want to start with the fact that you are a third-generation trial lawyer. Do you feel like you were born to be a trial lawyer, or how was it growing up in that family setting and dynamic? And when did you realize this is what I'm going to do as a career?

Josh: That's such a great question. It'd be the first question I would ask me, probably. First of all, it was a great honor and a unique experience to grow up marinating in what trial lawyers do. I'm very mindful of that being a true gift and a unique childhood. So I consider it a little bit of a double-edged sword professionally. On the positive side, it's a very sharp edge. The type of law I was exposed to, of course, was that of the fighter in the trial lawyer. So my grandfather was a very majestic, elegant statesman type of trial lawyer. When he spoke, he spoke in this very commanding baritone, like wisdom. No matter what he said, it sounded wise. You could say, the Mets lost today, and it sounded wise, which they often did. But I loved my grandfather. I had a very close relationship with him, and from him I learned a lot of wisdom and basics, and saw the lawyer as a fighter for the underdog.

And then for my dad, I saw more of the lawyer as the steward, the storyteller, the human being, the empath. And both of them took on fights. They never asked the question: can we make any money off this case? That was not considered an appropriate question if you were a cause lawyer. And for that reason, our firm almost went bankrupt many times. But their idea was to be in service of a person who really deserved a fighter in their corner. And they were always taking on these big corporations or judicial power, governmental powerful interests. So I got this kind of sense that being a lawyer was really more of a service-type profession, and a little bit like a gambler and a fighter, really, for people who may never have had one in their corner. And so it was a very idealistic view. From that standpoint, all of the things I learned from them definitely made whatever success I've had. You stand on the shoulders of my dad and my grandpa. And it was great, but it's also intimidating.

Ray: Do you remember how old you were the first time you were in court?

Josh: No, but I remember driving my grandfather to court and standing outside waiting for him to come out. He would have to get to court hours early. He and I were very different in this respect. I always had to leave way before and go really slowly on the highway. So I remember him saying, if I went 55, whoa, slow down, where's the fire? And I would look behind me at a long line of traffic honking, which he was apparently oblivious to.

Ray: Was there a certain case when you were younger that either your father or grandfather took on that remains one of those core memories of, this is what being a trial lawyer is all about?

Josh: Well, yeah, in a sense. My dad and my grandfather represented the Black Panthers in the 70s. And I remember being probably dragged to the lawn in New Haven to a protest. And it was at that time that I learned they were doing something that a lot of people felt strongly about, that was important. I don't think I really understood the full parameters of that, but I knew they were involved in something that was a different type of job than my friends' parents had.

And then there were other off-the-court kind of experiences. We had incidents that were pretty intense, like at that time in our history representing the Black Panthers, or suing for integration in the city, which my dad did. It got a lot of detractors, sort of like when I filed the Sandy Hook case and a lot of people were angry about it. And in the segregation cases, there were a lot of racists. So I remember my dad getting a call late at night and having somebody threaten to kill him. So those are the kind of things, and I thought, wow, my dad is doing something really, really dangerous. But I kind of had a sense that it was the right thing to do.

Ray: When did you hit the point where you're like, I'm going to be a lawyer and I'm going to do this? Or was it just sort of baked in that it was the obvious thing?

Josh: Yeah, first of all, I didn't know that 99% of lawyers don't do the type of law that we do. So I always thought all lawyers went to court and had a client they were arguing for. And I figured the other side had lawyers too, what I would consider the powerful or well-resourced side. I was always going to be this kind of lawyer if I was going to be a lawyer. But because of how well-known my grandfather was, and how revered he was, and because of how exceptional a lawyer my dad was, which was also a shocking thing to come to realize, because I always thought he was just another dorky dad, the dorkiest of the dorky dads. But my dad was really exceptional. My grandfather was good. My dad was better. But you know, it doesn't really matter.

What matters is that you worry in that situation about torpedoing the legacy. And so it's high risk from my perspective. I didn't have any confidence. So all of that was pushing against trying. I didn't want to try and fail. I'd rather not try. So there was that side of me. And then the realization that I didn't think there was anything else I really was interested in. And I was a little bit ambitionless. So when my dad said, hey, why don't you go to law school, I was like, oh. And he said, well, what's wrong? I said, well, I don't know if I could cut it. He goes, well, if it doesn't work out, you can drop out. And I was like, okay, I can work with those low expectations. And on the other side, I'm like, boy, my dad really doesn't have much faith in me. But it worked out, and I did enjoy it. And then, of course, I got the traditional rough experience of the first five or six years.

Ray: So you mentioned you had this fear of torpedoing the family legacy. I want to ask you the reverse of that, though. Was there ever a time where you didn't want to just follow in their footsteps or be in their shadow, and you wanted to carve your own path? And I feel like I'm playing psychologist a little bit. But was there ever a point where you're like, my father and grandfather are great trial lawyers, but there's a different path here, a different way I want to do things?

Josh: Yeah, that's a great question. I have to say that I sort of went from zero to 60 in terms of my confidence and capacity. So it was not as indolent as that. I wasn't building on things. I was terrible until I felt I was reasonably competent. And I guess at some point along the way, after my first four or five years, which were not marked by great success, I realized I had to stop trying to be like them. My grandfather could quote Aristotle or Shakespeare in the courtroom, and it worked for him. My dad could be very emotional in the courtroom, and it just worked for him. My dad was the best storyteller. And I was somewhere in between. I wasn't being authentic enough.

So in the sense that I had to be my own person, yes. I just had to accept the fact that I wasn't polished. I had to accept the fact that sometimes I don't go from A to B, but go through several other letters before I get there, and that the jury would ultimately accept me if I was simply being authentic and straight with them. And that was sort of the way I would answer that. I never imagined that I'd have any of the type of cases that my grandfather or dad had. I really didn't.

Ray: Is there a case that stands out in the early part of your career that gave you the confidence that, yeah, I can do this, and I'm figuring out my own approach?

Josh: Yeah, absolutely. I could pinpoint it. I'll just give you the brief version. It was a malpractice case, and it involved the death of a 50-year-old truck driver who died from a heart attack. The lawsuit named three defendants, a hospital and two doctors. The hospital and the main doctors who seemed to be at fault settled the case, leaving only a third doctor who had seen the man a year ahead of time. And at that point, the partner whose briefcases I was carrying said, well, Josh, why don't you take this last case? I'm like, thanks a lot. You settled the two really strong cases and you leave me with this.

And so I remember I had such little confidence, and it was such a hard case. And I called the widow, who was this wonderful woman who I'm still friends with today, and I effectively tried to talk her into allowing me to drop the case against this third doctor. They weren't offering any money, and I said, look, you have this great settlement. And she asked me a question that I don't even know if we'd be talking right now if the answer hadn't been what it was. There was an EKG done a year ahead of time, and she said if the EKG was normal, she would drop the case. But if it was abnormal, that's how she said it, was the EKG normal? So I was like, great, I've got my out.

So I go and I ask my expert, is the EKG normal? And the expert says, well, it's actually not normal. It's a nonspecific abnormality. So it wasn't necessarily abnormal, but the answer to her question was no, it was not normal. So at that point she said, I want to try the case. And you think about one thing that happens in somebody's life. For Gary, for my plaintiff, it cost him his life. For me, that answer led to what turned out to be the largest wrongful death verdict in Connecticut history, which was then overturned, and I tried it again and got a verdict that was about twice that. I'm only saying that not to brag, but I don't know what would have happened had that not happened. So that was the turning point for me. I felt, okay, I can get by, I can get through. Believe me, my track record sucked.

Ray: The other partner who left you to your own devices on that one, he wanted credit?

Josh: He wanted credit for it. No, he was pretty happy about it. He was pretty happy.

Ray: So I want to fast forward a bit to 2019. You bring this groundbreaking lawsuit against Harvard on behalf of a descendant of enslaved individuals who were photographed in 1850. Tell me about this case and the genesis of it.

Josh: Well, this was my dad's crown jewel case, the last case he ever handled. And this was vintage Michael Koskoff: dreamer, storyteller, believer that when you have something that is wrong, even if the law is against you, or not established, or no other lawyer would take it, it's your job to take cases for people who are deserving and who have been profoundly wronged, even if it means going up against a Harvard in a case that is over 150 years old.

So my dad wrote a movie called Marshall. In the movie was a cameo by civil rights leader Ben Crump, and it closed with Trayvon Martin's parents at the end of the movie. And there was a woman in Connecticut who went to an NAACP conference in Washington at which Ben Crump was speaking. And she walked up to him afterwards and said, Mr. Crump, I have a case. My ancestors were part of an experiment by Harvard. They were enslaved and the experiment was done by a racist Harvard professor. And Harvard is refusing to engage with me. Do you know anybody who can help? And she was from Connecticut. And Ben Crump's reaction, which was my reaction, and which was what my dad first told me, was, I think the statute of limitations expired about 170 years ago. And then he said, well, I think there's this guy named Mike Koskoff who might be just crazy enough and interested enough to take the case. And so my dad got the story and he was off to the races.

And when he presented this story to me, you can't hear the story and not think it's incredible. He came in beaming, and he asked me what I thought. I said, I think it's amazing. I said, I think you're probably thinking what I'm thinking. I'm thinking it would make a great op-ed in the New York Times. He's like, no, no, no, I'm thinking about a lawsuit. And I was like, all right, dad, I think you're finally losing it or something. But he was so animated, and it was his idea to bring the lawsuit that ultimately was successful in allowing us to prove our case in court on a case that has its roots back to 1850. And it's been a remarkable case that was only made possible by something he really trained me about, which was: be optimistic. If something grabs you, don't let difficult challenges or the law get in the way.

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Ray: Again, I'm joined by Josh Koskoff of Koskoff, Koskoff & Bieder in Connecticut, for those just tuning in to Raising the Bar with RebuttalPR. Josh, I want to pivot next to Sandy Hook, which is probably the case over the last several years you and your firm have become most known for. I want you to walk me through when you get that first phone call, and I'm not sure if it was a family member or someone connected to them, saying this family member needs help, and just what that process was like.

Josh: Yeah, I remember it, of course, like everybody remembers where they were when Sandy Hook happened. And Sandy Hook, Connecticut is about 20 miles from where I'm sitting right now, so we're right within the earlier ripples of it. And I will say that even before I was asked to help as a lawyer, and this is one of the real benefits of being a lawyer, something can happen that's terrible, and instead of having that feeling of, well, I wish I could help and knowing you can't, at least as a lawyer you know you have the possibility of being a help.

So what I wanted to do was really just to help these families any way I could, even before I got introduced to them, helping them get through probate or whatever. And it turned out about a week afterwards I was getting a ride to the airport to go to Chicago for a deposition. And the driver, upon striking up a conversation, found out I was a lawyer. And of course, when you tell a stranger you're a lawyer, after they ask you what you do, you have no idea what's coming next. Is it going to be a lawyer joke? Are they going to ask you for advice on an area you know nothing about? Or is it just going to shut the conversation off? And he said his friend needed a lawyer because his daughter was just killed in the Sandy Hook shooting.

And I remember, honestly, Ray, I bowed my head almost. I was not expecting that. And of course, I said, well, if there's literally anything I can do, even if just somebody to talk to, please give him my name. And he did, and that led to my representation. And at the time, I had no idea, I had no agenda, I had no plan. All I wanted to do at first was listen, find out how these people needed my help. I was never expecting to be hired to do anything. It was just going to be, what can I do? And I think any lawyer in Connecticut, or probably across the country, who does what we do would have wanted to do the same.

Ray: It had long been assumed and realized that suing a gun manufacturer was impossible. And I know Connecticut has a specific law that you brought a case against Remington under. When did it click for you that there's something here, that we could go down this road?

Josh: Well, it clicked... first of all, I don't want to give any false impressions. I didn't know what I was doing. I did not know anything about the law on guns. I knew nothing about guns or the industry. So I was completely ignorant in a way that may have, on reflection, been an asset for my willingness to really keep my mind open. Because the law, as I found out, was terrible. The gun industry, I knew it was powerful, and I would have said it was hard to sue them, but they had won all these immunities through Congress.

But you know what clicked, Ray? This is where I really go back to the soil of my childhood and my exposure to what my grandfather did and my dad did, and their view of the law. What I knew was, I knew it was wrong. I knew what they were doing was wrong, halfway through, when I learned about the promotion, the marketing, and the way they pushed particularly AR-15s on kids. And I thought, okay, put aside whether people should have these guns, I'm not getting into that issue. But here's an industry that tells us all the time that it's not guns that kill people, it's people that kill people. Okay, so it seems to me that the last thing you should do is promote the killing of other people to kids and adolescents.

And that's when I thought we have something that is absolutely wrong. And I learned it was all private equity-backed marketing strategy. And I thought, this isn't even the gun industry, per se. This is private equity, which is up there in terms of the industries that my grandfather and dad would have said have all the power and contribute to such pain and harm. And so I thought, we've got all the ingredients here. Okay, maybe we don't have the law completely on our side. But what I learned again from these hard cases that our firm has brought, more specifically my dad and my grandpa, is that you worry about the law later. If you've got something that's right and righteous, and you're on the right side of that, and there's something wrong by a big powerful interest on the other side, you're like nine out of ten parts there.

Ray: Is there ever a point where others at your firm or outside your firm pulled you aside and were like, Josh, I appreciate the enthusiasm, but you're tilting at windmills here? Or did you fear you were promising or leading the families on in a way that... could you deliver on taking on such a big case?

Josh: That's really cutting to the core question, because you do think about that. First of all, on the last point, the last thing I wanted to do was sell any false hope to these families. If I didn't think there was a case, as hard as it would have been to tell them, I would have told them. They'd been through so much, and to drag them through a case that was dead on arrival, I wasn't going to do that.

And then in terms of the pushback, the most distressing part for a while was that I expected a lot of pushback from, of course, the NRA and other vested interests, but I did get this kind of pushback from some peers. My dad was, of course, 100% behind me. He had no idea what the law was, but he was all on board with it because it was obviously right. I got some muted support at the time, and then there was some pushback. But you've got to stick your neck out sometimes.

I guess you don't really know when you're actually sticking your neck out to some people. But when you commit to families... look, I would have been the first to say, who is this crackpot lawyer bringing this case, if I hadn't spent almost two years looking into the facts and drawing a direct connection between what this private equity-backed gun conglomerate did and the Sandy Hook shooting specifically. I would be the first to say, wow, that sounds like a crazy case. So I don't begrudge people being a little bit cynical or pessimistic. Although in general, cynicism and pessimism to me is the place where cases go to die.

Ray: So after Sandy Hook, and I'm not sure how long after, there was this tweet that has become sort of infamous. It has to do with Congress really failing to pass any gun control. The tweet went something like, the gun control debate ended after Sandy Hook, when essentially Congress shrugged its shoulders at the idea of children being murdered. And I wonder, despite accomplishing so much for these families, school shootings still happen at such an alarming rate. Alex Jones is still out there to some degree; he doesn't have the empire he wants. Does this ever deflate you or make you question, what are the limits? The civil justice system can accomplish so many great things, but it also has its limitations, I guess, too. I know I packed a lot in there.

Josh: I think it may highlight both. The failures, really the abject failures, the indescribable failures of this government to protect children and all of us, I don't know if it'll ever go down in history as the darkest stain, because history may never change. So there may not be any looking back. But I can say that I was in Washington during the hearings after Sandy Hook, and it was more hopeful then. But then 10 years later, I was there with the Uvalde families, and Congress couldn't even pass raising the age on an AR-15 from 18 to 21, and that would have prevented the Uvalde shooting. So it's correct that at this point it's a fool's errand to trust Washington to do anything.

In my mind, that makes it more important to take alternative approaches. And I always think of that as a secondary thing that's in play in any case. But the first thing is, you have families that have just had their lives shattered. Your job is to represent them. And I do think that this highlights the importance of the civil system versus the futility of it. There are three branches of government for a reason. On almost a daily basis, we see how important that is and how scary it is when all three start to crumble. So I kind of view Congress's and the government's ineptitude and lack of courage as just heightening the importance of addressing things like this from outside the Beltway.

Ray: You said earlier that cynicism is where cases go to die. And you strike me as actually a pretty hopeful and optimistic person. What makes you optimistic about the civil justice system and its ability to drive change and a better future?

Josh: This is really what was inherited from my dad. He would always put an optimistic spin on everything. And so I figured if I was going to survive in this, I would have to do the same. But I guess it's because as long as there's a system in which you can get up in a courtroom and tell a story that is supported by particular facts in a case to human beings, not through television or a tweet or some talking head politician, but directly, from both the heart and the head, the right side will always prevail. When I say always, I mean almost always.

If you can have a direct conversation with people, your community, we have within us a collective empathy, a collective humanity, and a collective common sense. We're not the worst part of ourselves when we're together. And I just believe, as my dad did and finally got through to me, that if you can reach people and get rid of all that stuff, then it'll turn out right. It'll turn out right.

Ray: With that, Josh, thank you so much for joining the podcast. Really appreciate your time, and thanks for all you've done and all you continue to do.

Josh: Thank you very much, Ray. Really, really appreciate it.

Thanks for listening to this episode of Raising the Bar with RebuttalPR. Don't forget to subscribe and follow to join us next time. See you then.

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