History of a lot of serendipitous events, a lot of things that happen, and then this causes that to happen, this causes to happen, and then suddenly I mean, look at how World War I happened. No one could possibly have predicted that the assassination of the Archduke would have led to that point the worst war in human history, to be only dwarfed by World War II. No one could possibly have predicted that assassination would have caused World War I.

The slings and arrows of outrageous fortune. Welcome to Cited Authorities. My guest today is C. Evan Stewart. Evan is a retired lawyer, teacher, author, and longtime legal columnist. His career includes senior financial services roles, securities and financial services litigation, professional responsibility work, decades of teaching, roughly 300 legal articles, and recent books on legal and American history, including William Henry Seward and the Secession Winter, which I have here today. Evan, welcome to Cited Authorities.

Thank you, Alex. It's a pleasure to be with you.

Your author bio says that you retired in 2025 after more than 47 years practicing law. Of course, now you have a subsequent career as a prolific writer. What has surprised you most about looking back on the profession, the practice of law from just outside of it?

Now that I'm outside of it, I don't think of it too much, other than when I'm talking about my second book, which people ask me about quite a bit, the worst Supreme Court decisions ever. So to the extent I'm focused on the legal profession now, it's mostly about the court. The book I wrote about the court, the worst Supreme Court decisions ever, and people's current perceptions about the court, more importantly, Alex, misperceptions about the court. The amount of misinformation and thus misunderstanding about what the Supreme Court has done and is doing is very disheartening. If people only read, for example, certain East Coast newspapers and only watch certain cable news shows, they would have a completely wrong, totally misguided understanding of what the Supreme Court is doing. To that extent, that's been my focus on the legal profession since that book came out and I stopped practicing law. And I've kept I'm still still very, very interested involved in insofar as that. Reflecting back on the legal profession, now that I've been out of it almost 50 years, it's amazing how much it's changed. I told my law students for the over three decades I taught law students that change is getting faster all the time. And the idea that that pace of change is going to slow down at any time soon is simply illusory. So just the impact of AI on the legal profession. We're already seeing who could have predicted five years ago that AI would have this potentially revolutionary impact on the way people practice law. No one saw that one coming at all. And so where are we going to be in five years from now? That's a fool's errand to try to predict. But all I know is it's going to be really different in another five years than it is even today. So that's something that when I reflect back when I got out of law school in the 1970s, boy, it is really different for young lawyers starting with law practice, for people in mid-careers and older lawyers like myself.

And can you think of any seismic shifts that are comparable to AI that happened throughout your career with the advent of the Internet or other technological developments and how you managed to thrive throughout that change, and then offering advice to younger attorneys who are no doubt going to experience similar seismic shifts.

Yeah, no doubt the Internet changed law practice quite a bit just by the way lawyers and their clients communicated with one another. And that was not necessarily for the better, frankly. And also the way information is stored. When I started law practice, document production really was document production. You went to a warehouse and selected documents to be copied. That's not the way document production has been done for quite some time now, because of the internet. And so that's changed a lot. And so that dynamic, I think, is a very dangerous one for young lawyers because it's the young lawyers who understand technology, but it's the older lawyers who don't understand the technology that are supervising the young lawyers as to what they should be looking for. So there's a very important potential disconnect there between the older supervising lawyers who really don't understand. When someone says uh there's 75 gigabytes of information that we have to go through, someone my age really doesn't know what that means, but more importantly, knows how to direct someone your age or younger how to go and make sure you get not just some of the relevant materials, but all the relevant materials. Because at some point in the process in the trial, you're going to be making uh a certification to a court that all of the relevant materials have been produced. As an older lawyer, you're completely clueless to make that certification because you don't understand the technology well enough to really know whether that's true or not. But a younger lawyer maybe has not looked in all the right places because the older lawyer didn't tell him or her to look in this place or that place. They just used their own judgment based upon nothing, because they just got out of wall school, uh, to I'm I'm gonna just look over here, and they didn't look over here as well. So that's very dangerous for sure. The other thing I would say a seismic shift, and this happened for the earlier part of my career, but it's continued to have a huge impact on the profession, is this overwhelming obsession that lawyers have on their compensation, and which thus directly ties to client loyalty, loyalty to your partners, or non-client loyalty, andor non-loyalty to your partners. It used to be that you joined a law firm out of law school, and if you were lucky enough to make partner, you stayed there for your entire career. Uh, that was the paradigm. That paradigm has completely changed. I'm not gonna say for better or for worse. I'm just gonna say that that's just completely different today. But people, the the amounts of money that people now want to be paid, think they should be paid, uh, and if they're not being paid, they leave for some other place to stay there for two years until they go to another place to stay for another two years. That's very different. And I don't know whether that's gonna stay the same or that will change too. But those are some of the things that for sure change, seismic changes.

That's sage wisdom thinking about how perhaps, like you said, there could be a need in the market, a market gap that I don't see any technology firm in the legal field filling when it comes to younger attorneys may have more experience with AI and technological shift that's happening, but older, more experienced attorneys, of course, have a wealth of knowledge when it comes to the practice of law. So something to help bridge that gap to help younger attorneys explain the technology to more experienced attorneys who may not be as familiar. That's fascinating. I agree that it's a fool's errand to try to predict with any certainty what the state of the practice of law or the technology will be within five years. I don't know what's going to happen to the billable hour. I think that may eventually go the way of the dodo, maybe sooner than many people think when it comes to the advent of AI or the continuing use of AI within the practice of law. It's going to be an interesting, perhaps, redistribution of leverage, too, when it comes to larger firms may cut their headcount because of AI, and smaller firms may have more leverage to complete tasks, take on clients that even five years ago would have been impossible for them to take on because of a lack of capital and human labor. So it's going to be very interesting to see how all this plays out within the next probably two to five years.

Yeah, the other thing to factor into all that is the impact of COVID, which made people start working remotely. And I know there's been a big push among some of my contemporaries in New York City to force people back into the office. And the partners are much more willing to come back to the office than the associates, not so much. But that's such an important part for younger lawyers to learn how to be a lawyer, which is just to follow older folks around like me to see what I do and why I do what I do. That's how I learn to be a lawyer. And once you break that knot, and people are just sitting in their apartments doing whatever they're doing, whatever assignments they get, but they're not following someone to see how they prepare for a deposition and how they take a deposition, things of that sort, or how they do a deal, or whatever part, whatever part of the law you're in, that mentorship thing seems to have moved aside here. I don't think it's really come back in the same way in the post-COVID era, and that will undoubtedly also have an impact on the practice of the law.

There are plenty of tangibles and intangibles that younger attorneys experience they gain just by simply being around someone who has been there and done that a million times, and it's like they could do it in their sleep. Uh and of course, trial work and litigation. Like there is no other way to learn other than observing and doing too alongside more senior attorneys.

Before we went on on the air, you asked me about the SEC trial that I recently had. One of my young partners up to me after the trial, and I want to blow my own horn, but was very quite effusive and thanking me for all the lessons I taught him on how to examine witnesses and how to do things that lawyers do. This was a partner. And I said, I'm really just doing what the people who taught me X number of years before. So I'm just passing on really what you should be doing in another 20 years to somebody else. And so that's a really important part of learning to be a lawyer. And this was a fellow who was probably 34, 35 years old.

Aaron Powell Then you you're one of the few Wall Street attorneys who has tried many cases without being a federal prosecutor. That's rare. I want to know more about your philosophy on trial work generally, and then more specifically about your philosophy on preparation, client counseling, and examination of witnesses, direct and cross.

I was very lucky in law school. I had the greatest professor of trial techniques who ever lived, a guy named Irvin Younger. You've probably never heard of him. And he was absolutely incredible. One of the things I'll never forget was, and he was absolutely brilliant. He was the most brilliant public speaker I've ever seen. Charming, fascinating stories, just unbelievable. And his trial technique techniques course was simply incredible. But I remember as a second-year law student, he was giving a talk to the second-year class in the Mood courtroom about some inconsequential, I don't even remember what the subject was, but it wasn't some earth-shattering thing. And I was standing up right next to him, right before he was about to start delivering his comments, and I'll never forget looking at his hands. And his hands were trembling. So here was this guy who's the most accomplished, seeming greatest natural speaker I had ever seen to that point, or have ever seen since. And this guy was terrified about going out in 10 seconds to talk to this group of nobody second-year law students. And that has stuck with me for 50 some odd years that there is no natural. So here's a guy who's incredibly uh brilliant, seemingly born to do this, and he wasn't born to do it. He had to learn how to do this just like the rest of us who put on our pants one leg at a time. That was a very important lesson to me. Because if he got nervous that it's okay to be nervous, if if he needed to prepare to do something to do it well, then I could probably do the same thing. So that gave me a lot of confidence that you don't have to be a quote natural to actually do things pretty well uh on your feet, right? Whether it's to speak extemporaneously, to cross-examine witnesses, to deliver an opening argument or whatever. And so that has stuck with me, that lesson from 50 some odd years ago, um, really like a blinding insight. So to the extent I've a philosophy, is that anybody can do it if they work hard enough. And so that's sort of been ingrained in me. Uh what I would say on top of that is I was incredibly fortunate that the first law firm I worked, which was a very distinguished top law firm, which had some of the best trial lawyers in the country, bar none. I got to work with these, these were all men at that time. I got to work with these men and just not just watch them in action and to prepare them for what they were going to do, but to just sort of absorb. We talked about this mentorship thing a minute ago, just to watch them. And again, realize that they're human too. And how did they learn how to do all this stuff? And I could learn from just again, literally absorbing, and I did. I was very, very I mean, these these men were really quite extraordinary. I was very, very lucky, very, very lucky. So you asked it also about cross-examining witnesses and direct examination. Totally different arts. Direct examination is much more difficult than cross-examination.

Well, that's fascinating.

You really don't know. You ask this open that it what did you do next? And then you have, okay, what's coming out of this person's mouth, right? So you've got to prepare them, but not to the point of a script, right? Because if a jury hears a script coming out of your witness's mouth, you're cooked. A lot of lawyers think witness preparation is having them memorize a script. It's completely wrong. The most important thing for a witness is to be authentic. Because a jury can smell an unauthentic person. I've seen jurors literally when a person is finished testifying, well, when a person's halfway through their testimony, literally turning in the jury box because they can't look at this person. Because they don't believe them. They don't like to be lied to, and they believe this person's lying to them. At that point, you're toast. Now, fortunately, this was happening to my opponents. If you see this phenomenon, you you're completely cooked. If there you want a fill philosophical point, this differentiation between cross and direct, a similar point. I always told witnesses the most important thing for you to do is to be the same person on direct that you are on cross, or more importantly, the same person on cross that you were on direct. Because if I ask you all these softball questions, what did you do next? and you're feeling very, very comfortable, then when some guy like me comes on cross-examination and is putting words in your mouth and making you say yes to every question. And pretty soon you don't like that because you feel like I'm a ventriloquist dummy and I'm just manipulating you. People don't like that. But that's what cross-examination is. So cross-examination is much easier, if you will, than direct, because I already know every answer to every question I'm asking you. Because if you give me a different answer than the one I'm expecting, I have a document that you wrote that says you're lying. Okay. Is the jury gonna uh like that? They're gonna like that I exposed you as a liar, but you're toast. So yeah, you you can give me a no answer to uh what has to be a yes answer is tails, tails you lose, heads I win. I win either way, it doesn't really matter. So cross-examination it really is much, much simpler because, again, someone who knows what they're doing, I already know every answer before you've actually opened your mouth.

For cross-examination, direct examination, a lot of tips and tricks, so to speak, out there, but one I haven't heard and seems so intuitive is the importance of consistency for the witness during witness preparation, talking about that importance of consistency on both direct and then cross, or as you said, the importance of consistency on cross when the jury has already heard the responses to the direct examination questions.

Yeah, if the j if the jury sees a different person on cross than they saw on direct, whatever side you're on that's the this uh proposing that witness, you're toast. And that's that's the in my experience, that's the key to witness preparation. To have the witness uh understand uh that uh I'm there to protect you. Don't worry about uh what the answer is. Be yourself. I'll give you a great example of this. I was trying a case in arbitration down in Texas years ago, and uh a lot of money was at stake, and the key witness was this very, very able, very bright woman who had gone to a fabulous university, gotten a fabulous MBA at the best business school in America, had this incredible career at the best investment banking firm in the country, if not the world. And she was this this case was all about her, because the the people who were suing were saying that she screwed up. And she thought this was gonna be the end of her career. That this was like, I've never failed at anything, and I'm about to be pushed over the edge of uh Niagara Falls without a barrel, and this will be I'm dead. I said, no, no, no, no, no, no. Just take it, calm down. We're gonna get you through this. This is all fine. I told her some of these things, I've just told you about being the same person, and so we're in the middle of this hearing, and she's on the stand and direct has gone very well, and then on across, this guy is doing a pretty good cross on her because he's asking her, Isn't it true that she has to say yes? Isn't it true that she has to say yes? Even if she takes a break, or we take a break. Bathroom break, she goes to the ladies' room. I'm sure to throw up. And I'm sitting there about seven or eight feet away from the arbitrators. And two of the arbitrators, uh, I don't remember the third, frankly, because that's not important for the story, but two of the arbitrators were these very elderly, distinguished southern gentlemen. And one of them turns to the next one and says, What a nice young lady. I immediately jumped up. I ran out of the room, stood outside the lady's room when she came out. I said, We've won the case. She said, What do you mean we've won the case? I just threw up. I'm being sticked to my stomach. This is the worst moment of my life. I said, No, no, no, no, no. The arbitrators think you're a nice young lady. We've won the case. I said, What are you talking about? I said, nice young ladies don't commit securities fraud. We've won the case. I've told that story. Uh it's not the first time I've told that story because that's the key. If the arbitrators or the jury or who whoever is deciding your fate think you're a nice person, right? That's all you need to do. Right? So my job is to make sure that that personality is on exhibit, even when you're being asked nasty questions and you feel like I don't, I'd there, there are a thousand other places I'd rather be than right here, right now. This is horrible. No, be a nice person and the same person you were on direct, and everything will be fine. So that's my nice young lady story on how to be a good witness.

Like you said, nice young ladies don't commit securities fraud. And we have a desire for cognitive consistency. We don't want to think that someone who's a nice person could commit something that will degrade that image we have of them. So we're going to look at things in a way that is consistent with that image. And I think that's something they don't teach you in law school and is a very practical skill to know about. Getting a little bit more into the nitty-gritty, Evan, um, before you were outside counsel, you were general counsel at NECO Securities International and head of litigation at EF Hutton. What did those in-house jobs teach you about what clients, corporate or otherwise, truly need from their lawyers?

Yeah, so it's a very different role for lawyers. I was in a private firm for a number of years before I went and took the Hutton job. And then after the Hutton job, I took the general counsel position at NECO. It's a completely different experience. So you don't have to worry about getting or retaining clients because the client's right there every day 24-7. Um the demands on an in-house lawyer are very different. Um and it's it's the challenge of having one client as opposed to many clients. Um now, the job of head of litigation is at a at a large financial services firm is different than being general counsel. So that when I was at EF Hutton, there were a lot of fires that were going on all the time. That my job was to somehow manage that process and with within some degree of sanity to make sure that money that had come in wasn't going out in the in the form of settlements or or judgments at trial. And I found that really interesting. And I had a great group of colleagues and found that very, very interesting. The NECO thing was a little a little more different, or a lot more different, insofar as that was a the American arm of a Japanese securities, one of the humongous Japanese securities firms, one of the largest securities firms in the world. And so we had a a cultural and language issue as well to deal with. So uh the Japanese legal system, completely different. The way people communicate, Japanese to Japanese, Japanese to American, Americans to Japanese, very, very different. So that was, in a sense, it that was a very different learning experience because one of the most important things for any lawyer is to have uh a very effective two-way street of communication between yourself and your client. And if the client has a cultural problem, that they don't talk to lawyers that way, number one. And number two, they don't talk to Gaijin like Americans that that way. I've got to overcome both of those barriers to make sure that the company is getting good legal advice and following that advice. So that was something new and different for me. I'm glad I had that experience. But that was that was different. That was different for sure.

While you were practicing. What did teaching those students year after year? Yeah. What did that teach you about the practice of law?

I got into teaching initially because there'd been one of the things we talked about before we got on the air, uh and a little bit on the air, uh, is I was very concerned with some of the things that were happening in the legal profession, particularly insofar as they dealt with issues involving in-house corporate lawyers, which I was at that point when I started teaching. I thought some of the risks and challenges to lawyers in those positions like myself were reaching a point which really just were out of control almost. And so I wrote a number of articles, and that led the Fordham people to ask me to teach a professional responsibility. And so that's how I got initially involved in that. Then Cornell came about a decade later and asked me to teach a course for undergraduates who wanted to go to law school. And so I constructed an entire course, an introductory course, uh, sort of give them a flavor for what it's like to go to law school, a primer on the law school experience. And those are two very different teachers. And the Brook, the Brooklyn was also a professional responsibility set of courses. So the two law school teaching assignments were pure ethics, and the Cornell one was on a much broader base. What did that teach me about the legal profession? As I say, the ethics was a constant primer of how difficult it is to practice law. The challenges for people who represent public companies. So whether you're an in-house lawyer at a public company or an outside lawyer representing a public company, there are a lot of risks that I didn't think people were teaching law students about those risks, and that they needed to know about those risks, and that there were no easy answers to deal with these risks.

Like what? Could you give some examples of those risks?

Okay, so what do you do if the boss, the CEO doesn't follow your advice?