C. Evan Stewart: Wall Street Trial Lawyer and Prolific Author

ALEX POWELL: 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.

C. EVAN STEWART: Thank you, Alex. It’s a pleasure to be with you.

ALEX POWELL: 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. Uh, what has surprised you most about looking back on the profession, the practice of law from just outside of it?

C. EVAN STEWART: Uh, well, now that I’m outside of it, I don’t think of it too much other than, uh, when I’m about my second book, um, which people ask me about quite a bit the, the worst Supreme Court decisions ever. to the extent I’m focused in, focused on the legal profession now, uh, it’s mostly about the court, uh, the. The book I wrote about the court, the Worst Supreme Court decisions ever and people’s current perceptions about the court, and, and more importantly, Alex misperceptions about the court, the amount of mis mis, uh, information and the, and thus misunderstanding about what the Supreme Court has done, and is doing is, uh, very disheartening. the, um, if people only read, for example, certain East coast newspapers and only watch certain cable news shows, would have a completely wrong, uh, totally misguided understanding of what the Supreme Court is doing. And, uh, so that to that extent, that’s been my focus on the legal profession, since that. That book came out I stopped practicing law. I’ve kept, I still am very, very interested involved in insofar as that, as far as reflecting back on the legal profession, uh, now that I’ve been out of it almost 50 years, it’s, it, it’s amazing how much it’s changed it, it’s going to, I, I told, I told my law students for the over three decades I taught law students, the, the, the change is getting faster all the time. And the idea that it’s that, uh, pace of change is gonna slow down at any time soon is simply, um, illusory. uh, just the impact of AI on the legal profession we’re already seeing. mean, who could have predicted five years from ago, uh, that AI would have this? Potentially revolutionary impact on the way people practice law.

No one, no one saw that one coming at all. And so where are we gonna be in five years from now? That’s a fool’s errand to try to predict, but all, all I all I know is it, it’s gonna be really different in another five years than it is even today. So, um, that’s something that when I reflect back, I got out of law school in the 1970s, boy it is really different, uh, for young lawyers, uh, starting law practice for people, um, in mid careers and older, older lawyers like myself.

ALEX POWELL: Kevin, can you think of any seismic shifts? Uh. That are comparable, that are comparable to, to AI that happen throughout your career with the advent of the internet or other technological developments, uh, and how you manage to thrive, uh, throughout that change. And, and then, uh, offering advice to, to younger attorneys who are, uh, no doubt going to experience similar seismic shifts.

C. EVAN STEWART: 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, uh, frankly, and also the way information is stored. Uh, so in, in. 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’s been done for quite some time now because of the internet. And so, um, that’s changed a lot. Um, and, uh, so that, 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. uh, there’s a, a, a very important potential disconnect, uh, there between the older supervising lawyers, um, who, who really don’t understand when, when someone says, there’s 75 gigabytes of information that we have to go through. Someone my age. Really doesn’t a 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 gonna be making, uh, a certification to a court all of the relevant materials have been produced. As an older lawyer, you’re completely clueless to make that certification ’cause you don’t understand the technology well enough to really know whether that’s true or not. a younger lawyer 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. just used their own judgment based upon nothing because they just got out of law school, to, I’m, I’m gonna just look over here. They didn’t look over here as well. um, that’s very dangerous for sure. The other thing I would say, um, 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, uh, this overwhelming, uh, obsession that lawyers have on their compensation and, uh, which thus directly ties to, um, client loyalty, loyalty to your partners or non-client loyalty and or non, uh, loyalty to your partners. Uh, it used to be, uh, 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. And, um, I am not gonna say for better or for worse, I’m just gonna say that that’s just completely different today. But people, the amounts of money that people now want to be paid, think they should be paid. and if they’re not being paid, they’d leave for some other place to stay there for two years until they go to another place to stay for another two years. Uh, that’s very different and um, I don’t know whether that’s going to stay the same or that will change too, those are some of the things that for for sure, change seismic changes.

ALEX POWELL: Uh, that’s sage wisdom. Thinking about how perhaps, like you said, there could be a, a, a need in the market, a market gap that I don’t see any. A technology firm in the legal field filling when it comes to, uh, uh, younger attorneys may have more experience with, with AI and, uh, 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. Um, I agree. It’s a, 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, I, I don’t know what’s going to happen to the billable hour. I think that that may eventually go the way of the dodo, um, maybe sooner than many people think. Uh, when it comes to, uh, the advent of, of ai. The continuing use of AI within the practice of law. Uh, it, it’s going to be an interesting, perhaps redi redistribution of leverage too, when it comes to larger firms may cut their headcount, uh, ’cause of ai and smaller firms may have more leverage to complete tasks take on clients that even five years ago would’ve been impossible for them to take on, uh, because of a lack of, uh, capital and, and human labor.

So it’s, it’s going to be very interesting to see how all this, uh, plays out within the next probably two to five years.

C. EVAN STEWART: The other, the, the other thing to factor into all that is the impact of COVID, made people start working remotely. And, uh, I know there’s been a big push among some of my contemporaries in New York City to, uh, force people back in the office. Uh, and the partners are much more willing to come back to the office than the associates.

Not so much. Um, but that’s an, that’s such an important part for younger lawyers to learn how to be a lawyer, which is. to follow older folks around like me, see, see what I do and why I do what I do. That’s how I learned to be a lawyer. And, uh, once you break that knot and people are just sitting in their apartments whatever they’re doing, whatever assignments they get, but they’re not carrying someone’s bag to a courtroom or not following someone to see how they prepare for a deposition and how they take a deposition, things of that sort, uh, or, or how, how they do a deal or what, whatever part, whatever part, the lawyer you’re in, um, that, that mentorship thing, uh, seems to, uh, moved aside here.

I I, I don’t think it’s really come back in the same way, uh, in the post COVID era. And that will have a, that will undoubtedly also have an impact on the practical law.

ALEX POWELL: I agree there are plenty of tangibles and intangibles that younger attorneys experience they gain just by simply being around someone who, who has been there and done that a million times and it’s like, uh, they could do it in their sleep.

C. EVAN STEWART: Yeah.

ALEX POWELL: of course, trial work and litigation, like there is no other way to learn other than observing and doing too alongside more senior attorneys.

Uh, so Evan, I agree with you. Of course you’ve had, please.

C. EVAN STEWART: I’m sorry. No. Before we went on, on, air, you asked me about the SEC trial, uh, that I recently had. Um, one of my young partners came up to me after the trial was, I don’t wanna blow my own horn, but it was very, quite effusive in thanking me for, um, all the lessons I taught him, uh, on examine witnesses and how to. Do things that lawyers do. This was a, a partner um, I said, I said, well, I’m really just doing what the people who taught me, uh, 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, uh, so that’s, that’s a really important part of learning to be a lawyer. And this was a fellow who was, uh, probably 34, 3, 5 years old.

ALEX POWELL: Evan, you’re one of the few Wall Street attorneys. Uh. Who has tried many cases, uh, without being a federal prosecutor. You tried cases in private practice, big time cases, uh, and that’s, that’s rare. That’s rare. I, I want to know more about your philosophy on trial work generally, and then more specifically about preparation and client counseling without getting into specifics of particular clients, but, uh, your philosophy on preparation, client counseling and examination of of witnesses direct and cross.

C. EVAN STEWART: So, um, I’m not sure I have any Grand pH philosophy. Uh, at least I I didn’t try to jot one down on paper before we started. Um, uh. I was very lucky in law school. I had the greatest professor of trial techniques, uh, who ever lived, a guy named Irving Younger. You’ve probably never heard of him, and he was absolutely incredible. And, um, of the things I’ll never forget was he was absolutely brilliant. He was the most brilliant public speaker I’ve I’ve ever seen. none charming, fascinating stories. Um, just, just unbelievable. And trial technique course was simply incredible. But I remember as a second year law student, he was giving a talk to the second year class, uh, in the moot courtroom about some. Inconsequential. I don’t even remember what the subject was, it wasn’t some earth shattering thing. I was standing up right next to him, uh, right before he was about to start delivering his comments. And I, I’ll never forget looking at his hands and his hands were trembling. So here was this guy who’s the most accomplished, uh, seeming greatest natural speaker I had ever seen to that point, or I’ve ever seen since. And this guy was about going out in 10 seconds to talk to this group of no nobody, second year law students. And that was a very, that has stuck with me for 50 some odd years that, uh, there is no, there is no natural, uh, there is. So here’s a guy who’s incredibly brilliant, seemingly. Born to do this, and he wasn’t born to do it. He, 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, uh, if, if he would, if he got nervous that it’s okay to be nervous, if he needed to prepare to do something to do it well, then I could probably do the same thing. that gave me a lot of confidence that you don’t have to be a quote natural to actually do things pretty well, on your feet, Whether it’s to speak extemporaneously, to cross examine witnesses, to deliver an opening argument or, or whatever. so that has stuck with me, uh, that lesson from 50 some odd years ago. I. Really like a blinding insight. Uh, so to the extent I have a, have a philosophy is that, uh, anybody can do it if they work hard enough. And, uh, so that’s sort of been ingrained in me. The, from a, again, I hate to be try to talk about philosophy. What I would say on top of that is I was incredibly fortunate, uh, at, at the first law firm I worked, which was a very distinguished, uh, 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 gonna do, to just sort of absorb. We talked about this mentorship thing a minute ago, to watch them. And again, realize that they’re human too. Um, and how did they learn how to do all this stuff? And, and I could learn from just again, literally And I did. And I was very, very, I mean, these, these men were really quite extraordinary. And, um, so I was very, very lucky. Very, very lucky. So, um, you asked it also about cross examining witnesses and, uh, uh, direct examination. Totally different arts, direct examinations. Much more difficult than cross-examination

ALEX POWELL: Well, that’s fascinating, right.

C. EVAN STEWART: Yeah. You, you really don’t know. You, you asked this open, what did you do next? And then, then you have, okay, what’s coming out of this person’s mouth? Right? you’ve gotta prepare them, but not to the point of a script. Because a, a, if a jury hears a script coming out of your witness’s mouth, cooked. A lot of lawyers think witness preparation is them memorize a script. It’s completely wrong. The most important thing for a witness is to be authentic. ’cause a jury can smell an unauthentic person. Uh, 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 ’cause they can’t look at this person. ’cause they, they don’t believe them. They don’t like to be lied to, and they believe this person’s lying to them. Well, that point you’re toast. it’s, this was happening to my opponents, but, uh, if you see this phenomenon, you, you’re completely cooked and, and another. If there, you want a Phil philosophical point? This differentiation between cross and direct si. A similar point. I always told witnesses, the most important thing for you to do to be the same person on direct you are on cross, or more importantly, the same person on cross that you were, 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 is putting words in your mouth and making you say yes to every question and pretty soon you don’t like that you feel like I’m a vent you’re a ventriloquist dummy and I’m just manipulating you People don’t like that but that’s what cross examination is So the 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 a document that you wrote that says you’re lying Okay the is the jury gonna like that Well 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 has to be a yes answer but I win uh you know I win Uh it 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

ALEX POWELL: And I’m also thinking about how, for cross examination, direct examination, a lot of, you know, tips and tricks, so to speak out there. But one I, 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, or as you said, the importance of consistency on cross when, when the jury has already heard the responses to the direct examination questions.

C. EVAN STEWART: Yeah if

ALEX POWELL: Evan?

C. EVAN STEWART: the jury if the jury sees a different person on cross than they saw on direct uh Whatever side you’re on that’s that that’s that witness you’re toast And um that’s that’s the in my experience that’s the key to witness preparation to have the witness understand that I’m there to protect you Don’t worry about what the answer is Be yourself I’ll give I’ll give you if you have a second I’ll give you a great example of this I was trying a case that I was trying a case in arbitration down in Texas ago and uh of money was at stake And the key witness was this very very able very bright woman who had gone to a fabulous university uh gotten a fabulous uh 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 the the the who were suing were saying that she screwed up and she thought this was gonna be the end of her career The this was like I’ve never failed at anything and I’m about to be pushed over the edge of of Niagara Falls without a barrel and this’ll be I’m dead I said no no no no no no Just take it Calm down We’re gonna get 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 blah blah blah blah And so we’re in the middle of this hearing and she’s on on the stand and uh direct has gone very well And then on cross this guy is doing a pretty good cross on her 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 she takes a break Uh or we take a break uh bathroom break She goes to the ladies room I’m sure to throw up I 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 cause 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 a nice young lady I immediately jumped up ran out of the room stood outside the ladies room when she came out and said we’ve won the case He said what do you mean we won the case I I just threw up I’m being stick to my stomach The um uh 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 He 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 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 That’s all you need to do right So my job is to sure that that personality is on exhibit E even when you’re being asked questions uh and you feel like I don’t I there there are a thousand other places I’d rather be than right here right now Uh uh This is horrible Um no be a nice person and the same person you were on direct and everything will be fine So that that’s my that’s my nice young lady story on how to be a good witness

ALEX POWELL: Right. And, and like you said, nice young ladies don’t commit securities fraud, and we have a desire for cognitive consistency. You know, we, we don’t, we don’t want to think that someone’s a, a nice person could commit something that will, uh, degrade that image we have of them. So we’re going to, to look at things in a way that is consistent with that image.

I think that’s, that’s, uh, something they don’t, they don’t teach you in law school and is a very practical skill to, to know about. Um, getting a little bit more into the, the nitty gritty, Evan, uh, before you were outside counsel, you were general counsel at Nico 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?

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

ALEX POWELL: Evan, you, you taught for many years at Fordham and Cornell and Brooklyn Law School as well, while you were practic. Practicing, uh, what did, what did teaching those students year after year, what did that teach you about the practice of law?

C. EVAN STEWART: Uh well I got into teaching initially because uh there’d been one of the things we talked about before we got on the air and a little bit on the air Is uh I was very concerned with some of the things that were that that were happening in the legal profession uh particularly insofar as they dealt with um issues involving uh in-house corporate lawyers which I was that at that point when I started teaching And uh I thought some of the risks and challenges uh to lawyers in those positions like myself uh 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 uh professional responsibility And uh so that’s how I got initially involved in that Uh then Cornell came a about a decade later and asked me to teach a a course for undergraduates who wanted to go to law school And so I constructed an entire course an inter inter introductory course sort of give them a flavor for what it’s like to go to law school if you will a primer on the law school experience And uh those are two very different te and the Brook the Brooklyn was also a professional responsibility uh set of courses Um so the the two law school teaching assignments were uh pure ethics And the Cornell one was a a much broader based um did that teach me about the legal profession Well as I say the the ethics was a constant primer uh of how difficult it is to practice law The challenges for people who a public companies So uh whether you’re an in-house lawyer at a public company or an outside lawyer representing a public company uh there are a lot of risks nobody uh I didn’t think people were tea teaching law students about those risks uh and that they needed to know about those risks and that there were no easy answers uh to deal with these risks That

ALEX POWELL: Could you give some examples of those risks?

C. EVAN STEWART: okay So uh what do you do if the boss if the CEO doesn’t follow your advice

ALEX POWELL: Right.

C. EVAN STEWART: Okay So there was a very famous case in the early nineties It’s one of the reasons I got started teaching involving Salomon Brothers which was a the leading bond uh Uh a company on on Wall Street sold us treasuries and um the general counsel found out that the guy who was head of the trading desk of US treasuries was engaged in uh illegal conduct And he to the CEO and said what this guy’s doing is wrong It may even be criminal and we gotta do something about it And the CEO actually said you’re right I’ll make sure I I’ll talk talk to the people in Washington and and we’ll stop this Right So you think well gee the general counsel did the right thing He gave the right advice to his client The client didn’t reject the advice The client said great thank you I’m gonna act upon your advice and do the right thing You think the story’s gonna end in a good place It doesn’t because the CEO for reasons and still unclear today doesn’t call his friends in Washington at the Treasury Department do anything And then this guy the traitor doesn’t does what he was doing again the second time the guy does it he’s caught and all hell breaks loose Ultimately Salomon Brothers doesn’t exist anymore The trader goes to jail The guy is the CEO loses his job and still has enough money to I have a fancy apartment on York and a fancy apartment in Paris but he’s no longer the king of Wall Street But the guy who’s the general counsel he not only loses his job he can’t practice securities law ever again And the SEC writes this damning report about how this guy is completely screwed up Now you tell me how he screwed up Right He he uncovered the conduct He reported it to the boss The boss said thank you You’re right I’m gonna make sure this doesn’t happen again And he’s the one who gets screwed

ALEX POWELL: Right, right.

C. EVAN STEWART: Now

ALEX POWELL: has ethical obligations to, to the corporation as client as well. It

C. EVAN STEWART: well

ALEX POWELL: please continue,

C. EVAN STEWART: Yeah Yeah So what do you do though Right

ALEX POWELL: right?

C. EVAN STEWART: This guy the guy who’s the head of the firm his firm right You going over his head to the board of directors is committing Harry Carey That’s the end of your career okay That that’s what your ethics obligation tells you to do which is he doesn’t a agree with you of course he does agree with you but if he if he doesn’t agree with you you’re supposed to go over his head Well going over his head in that circumstance is the end of your career which is what happened to the guy anyway So how do you deal with this There’s an ethics problem there’s a corporate culture issue there’s a self preservation issue there’s a how do you one of the The SEC says this guy is responsible for is he failed to supervise the trader Well people I I don’t know whether you’ve done much work on Wall Street but the head of the trading desk at a major financial services firm on Wall Street makes 10 or 15 times what the general counsel makes and the general counsel for sure doesn’t rep doesn’t supervise that trader the head of the trading desk It’s just absolutely ridiculous There’s a fundamental problem in these you say about how corporations work in most corporations the general counsel or the the legal department they’re looked upon as um fiscal uh um swamps or drains or whatever They’re not making any money They’re just cost they’re cost centers They’re not revenue producers The people who are big big uh revenue producers those are the people who have power How do you how do you deal with this power imbalance in a in a especially in a public company Um you you can go to talk to one of these people all the all day long as a lawyer and say Hey I I don’t think you should be doing this And a lot of things these guys will say who the hell are you I I’m I’m I’m bringing a hundred million dollars this year or $500 million or a billion dollars or whatever You know what are you raising for the company this year You’re just costing us money Right Well that that’s a real power imbalance that lawyers have Lemme put it a different way When you’re a partner in a law firm you’re a revenue producer Right That gives you a lot of power So as long as you’re producing revenue but that that’s your job is to produce revenue right And the people who produce the most revenue in law firms are the most powerful right You go in in-house as a general counsel you’re not a revenue producer at at at all Your revenue production is zero So that changes a lot of power dynamic So when you say you must listen to me because I’m telling you this uh as a lawyer in this for your own good uh the person listening to you is looking at you uh not necessarily thinking thank saying Thank you for saving me from this situation saying get out get outta here so I can go back and make some more money Uh And so that’s that’s a very important thing that I I uh always tried to teach And through various different uh methodologies are other other important lessons So there’s a very important case by the SEC which says whenever a lawyer is faced with a problem whether it’s the one I mentioned before the Salomon Brothers problem or any other problem they have to give the right advice And if they don’t give the right advice you can destroy their career Now when this case says give the right advice it’s not just give the right advice but make make the client accept that advice And if if so if you say to the client here the here’s three ways you can address this issue And the client says well that’s interesting Uh I’m gonna choose option C And somebody comes five years later after there’s a corporate train wreck cause that’s when these things always are looked at after after there’s a catastrophe And says why did you give those people three options with the benefit of hindsight Option one was the only option you should have given them and you should have made them option one And so as a result we’re gonna destroy your career Uh that’s and and and and the language of this decision it’s a very famous decision uh is under these circumstances must be right all the time And what do you do with that Uh because When you’re in these circum um I hope you’ve never been in these circumstances but when you’re in these circumstances there’s not a lot of light and clarity It’s very confusing You people don’t have all the facts aren’t necessarily telling you everything can’t be everywhere at once but you you have to be right how often all the time And if you’re not five years from now is gonna be saying you failed to do the right thing or failed to implement the right thing or failed to make the client do the right thing And so your career is over Well that’s pretty tough And so these kinds of difficult lessons I mean I could go on but these kinds of difficult lessons I think are important For young students and soon to be young lawyers to understand this is a dangerous world you’re going into uh and with a lot where the got the goalposts are not necessarily completely clear number one this notion you have to be right all the time Well nobody’s I don’t know about you Alex but nobody’s right all the time Uh especially in very stressful and difficult circumstances there’s not a lot of clarity There’s a lot of smoke and and stuff going on knowing exactly what the right thing to do is is is pretty tough But I thought it was important to to teach people about the that stuff dangerous it is

ALEX POWELL: It’s so important because there’s obviously a disconnect between the expectations and the practical reality of practicing in those situations. Um, and then what, what, what’s the advice you’d offer students? Uh, it, it seems like, well. Perhaps the best advice considering the quandaries that you just discussed, i, i, is to, to be aware of the expectations, uh, and then, and then you can act accordingly.

C. EVAN STEWART: uh two things One is uh r recognize a recognize how difficult you especially in in the context of public companies uh where you have not just stockholder risk The there are different people who can come after you Stockholders can come after you and the SEC and other government agencies come after you the Department of Justice So there d there are different there are different potential enemies out there who who won’t like you Uh so recognize the That there are problems Number two when you’re in a situation like that go slow Uh think think again But more importantly don’t try to think for yourself So the third thing is uh seek some other advice So it’s very hard to be objective when you’re in the middle of an eye of a hurricane uh especially when you’re it’s your if you’re an inside lawyer you’re in the eye of the hurricane right You know all these so you know the guy on the trading desk you know the CEO They’re the people who hired you You’re having lunch with them every day You’re you’re friends with them right They’re paying your salary they’re paying your bonus right It’s hard to completely pull yourself away and be objective So have some people wherever they are whether outside law firms in academia whose judgment and experience um you trust and you can get some ob objective third party Hey I’m in a situation I’m not sure how to think my way through this do you think Right Because in most of in the circumstances in these famous cases that I teach and I’ve taught for what decades right people in the eye of the hurricane thought they were smart enough to get out of trouble by themselves And that that experience tells me that doesn’t work History tells me that doesn’t work And um It’s it’s tough to it is I won’t say it’s impossible to do but it’s extremely tough to figure this out all by yourself

ALEX POWELL: I’m thinking about law school classes generally, you know, contracts towards those are important of course, but you don’t hear advice, teachings that could save your career. Uh, the same way that the. That you do based on the teachings that you just explained. Um, Evan, I do want to be mindful of your time.

Do, do you have another, um, 10 minutes or so to continue discussing?

C. EVAN STEWART: time As much time as you

ALEX POWELL: Great. Great. Uh, I do want to discuss your writing and your, your latest book, William Henry Seward’s Quest to Save the Nation during the secession winter, which is available now. Um, e Evan, what, what was your inspiration for, for writing this book?

We talked about it off air, uh, but please let our audience know why you decided to write this book, uh, and why you decided at this point in your writing career to write this book as well.

C. EVAN STEWART: Uh so I was very fortunate when I was an undergraduate at Cornell I had two of the greatest historians in the country if not the world and the confluence of both of their disciplines had different disciplines was a man named William Henry Seward And uh one man was Professor Joel Silvy who was the country’s leading political historian And Seward was one of the most important politicians in America in the 19th century And the other man was Walter Lafe professor Lafe Who was the country’s leading diplomatic historian and Seward when he was a young senator in the early 1850s laid out an intellectual architecture for the expansion of the United States not just to the West coast but also to uh Asia to China and Japan And literally his uh architectural design is actually what took place So in his lifetime he buys the Guano Islands for Coaling stations to Asia He buys Midway Island He famously buys Alaska At the same time he’s buying Alaska uh sort of relevant for today’s body politic He was trying to buy uh Greenland He had a vision for the Panama Canal Uh he also had a vision for uh buying a number of islands in the Caribbean To make the Caribbean basically an American lake So many of these things got done in his lifetime Some were done by of his subsequent but it’s was you you read these speeches in 18 51 52 53 really quite remarkable that what he was talking about actually came to be Uh and so he’s been a an interest of mine for 55 some odd years Um after I finished my third book I should step back So at you’ve mentioned how many articles I’ve written over time Uh several of them have included articles about Seward So I’ve been Duns interested in Seward I’ve written a number of articles about him and published some uh over the course of my career Um after I finished my third book I was thinking about doing another uh article about Seward based upon led ultimately became this book And um so I wrote wrote a very very very very short version of this book uh and published an article And I thought that that really doesn’t do it justice because this is such an important subject that no one really knows about Um and the the litter the the archival material and the second the so-called secondary Um historical academic works uh need to be and revealed in detail because Seward’s role during the so-called secession winter uh hasn’t really been told correctly before this book uh the extent it’s been told at all Um it’s been told by historians who have this particular episode from Lincoln’s standpoint and uh that’s really not the right um in my judgment um way to examine this because Lincoln during the so-called secession winter Um after his election but before his inauguration on March 4th So you’ve got November December January February Lincoln stays in Springfield Illinois and says nothing publicly Uh a number of historians have called this believe it or not this period of doing nothing masterful inactivity which is sort of an interesting phrase Um but if Lincoln’s perfect we have to say him doing nothing while the country’s falling apart is masterful inactivity Okay well that’s one way to deal with it But let’s let’s actually try to as lawyers and not just historians but as lawyers let’s look at the evidence the evidence is one man during this period actually goes to Washington uh recognizing the existential threat and crisis that’s going on South Carolina Secedes the other Deep South States go with with her shortly thereafter country’s falling apart gotta do something about this Otherwise there’s not gonna be a country Uh Lincoln’s gonna be inaugurated but there won’t be a country And some historians literally have called what what uh sewer did to try to save the upper South and keep the upper south in the union Uh appeasement which was a very charged word from World War ii Neville Cha Chamberlain tried to appease uh the ultimate embodiment of evil Adolf Hitler Well gotta be careful here because trying to reach a compromise with slave owners that’s what this country was all about The Constitution is a compromise with slavery The 1820 compromise was a compromise with slavery The 1850 compromise was a compromise with slavery There lots of compromises with slavery so let’s be a little careful about that That’s a historical or unal depending on which which way you wanna use those words Um the some historians have also called it a profoundly mor profound moral def defect for him to try to stave the union without a civil war well I’m sorry civil War 700,000 people died um and another 700,000 lost their arms or legs or were never the same again Uh if that had happened in world that same percentage of casualties happened in World War ii So we wouldn’t have on to final victory People people would’ve gone nuts right It’s the worst war in our history Not even no other wars come anywhere close So uh was it worth trying to prevent that Um I I think so Uh one cause once you one this right now once you start a war it’s sort of hard to stop it cause once you start something you don’t know necessarily how it’s gonna you’re not in control of how it’s gonna end no matter how many how no matter what resources you bring to bear And so um was Seward wrong to try to do this Well let’s put that judgment aside here and let’s just see what he tried to do and whether it worked and what he did in fact Virginia North Carolina Tennessee and Arkansas the secession winter all voted not not to secede And why is that It’s because of William Henry Seward and they were poised to to continue that position Uh and when Lincoln becomes president Lincoln initially agrees with Seward’s approach to this especially with regard to Fort Sumpter to not try to resupply Fort Sumpter because that would be a trigger point that in the South’s mind trying to resupply Fort Sumpter would be evidence of so-called coercion It’s a critical word in this period uh if if the North did something to coerce the the southern states then the uh the Upper South would feel compelled to align themselves with the states in its decedent So in March Lincoln agrees not to resupply Fort Sumpter And then as March turns to April Lincoln changes his mind Very complicated story Uh and he changes his mind Um and Lincoln lovers who believe Lincoln was perfect aren’t gonna like this but this is just the case Lincoln made a decision to to resupply Fort Sumpter gotta emphasize that word knowing that that would cause the Civil War that was against Seward’s advice Um and it did the Civil War So um that story a story that’s really not been told because uh in particular if you remember Lincoln’s second inaugural address which I talk about in the book he talks about the start of the Civil War in the passive voice and then the war came Like it sort of just came like night follows day or day follows night Well no actually things caused that to happen his decision to send ships down to try to resupply for sump sumter this is clear beyond any doubt uh was uh militarily unimportant and more importantly militarily indefensible Uh if you’ve ever been to Charleston Harbor Alex see Fort Sumpter in the middle of Charleston Harbor you know that that it was ringed with um cannons aimed at it from every angle There’s just not a prayer of of two and two prior federal government ships had been fired upon and driven from Charleston Harbor in the preceding months So wasn’t gonna work important to the north in any event But Lincoln made that decision a very complicated decision but he changed his mind made that decision and the war came as he said

ALEX POWELL: What do you think would’ve happened if he decided not to do it in April?

C. EVAN STEWART: Well that’s something I’ve stayed away from in the book cause that’s so-called counterfactual history We’ll we’ll never

ALEX POWELL: Right

C. EVAN STEWART: right What Seward was What we do know is what Seward was trying to do was trying to get to the elections in Virginia So states at that time had congressional elections times of the year. Very different than our system now where it’s on every state does it in November. Right. Totally different than, and his strategy, working very closely with the, these pro-union men who’d already voted to stay in the union. Virginia had voted two to one to stay in the union prior to this point was if we can get to those May elections. Vote, have a cl clean slate of union supporting elected to Congress. will be a critical, uh, in trying to keep, keep this ball rolling or if you will keep the momentum of, of union sediment in the upper South. And the theory, again, the theory was, we’ll never know whether this would’ve worked, the theory was if you can keep these critical states, and of course Virginia was the most important, but North Carolina of course, but South Carolina, so if you can keep those two states and Tennessee, Arkansas is not quite as important as, but, and Kentucky, can keep those states ultimately.

And there’s a cartoon in my book that sort of highlights this, ultimately the so-called cotton states. South Carolina, Mississippi, Georgia, Alabama, they have so little in common, number one, other than slavery. And secondly, they really don’t have a viable economic, let alone political, uh, unified structure that without the upper South, they’re gonna have to ultimately come back with their tail between their legs, if you will. The, the, just the economic and other forces at play. They’ll have to come back now. Is that right? We’ll, we’ll never know. Would it have worked? We don’t know. Um, what, but again, what we do know is until. Lincoln sends those ships down to Fort Sumpter, the upper South held and was staying in the union we know. We know that beyond a shadow of a doubt, and up until literally up until the day they were about to sail into that Harvard Seward was still sending, uh, loyal union men from Virginia into the White House to meet with Lincoln to try to convince him not to do this. Um, so that much we know whether we know it would’ve worked and prevented a civil war a year from then, who knows?

And that that’s not my job. My job is combining the best of my professions as a historian and as a lawyer. Just look at the evidence. I’ve looked at all the, uh, I, I if you’ve looked, if you’ve looked at the end notes in my book, you know that I’ve looked at all the evidence. so I, I, I can’t predict what if, this is a book as to what did happen up until that point. um, it’s a story that should be told. And it,

ALEX POWELL: And it.

C. EVAN STEWART: think it, I don’t think it’s evidence of appeasement or a moral, a profound moral, a defect. It’s trying to prevent a war that killed 700,000 people. And the other other point to keep in mind is, oh, well the Civil War solved all our problems. Well, actually it didn’t, uh, there were a number of constitutional amendments that were passed after the war that purported to give African-American citizen and to end slavery and give African-American citizens the full, full privileges and immunities of American life. How did that work out? Well, for a hundred, not, not so well for a hundred plus years after that. I point, I point out frequently when people ask me questions about that, uh, re remember that the number of lynchings of black Americans in the South, in the 1930s and the 1940s, especially in the 1940s when black Americans were enlisting in the military to defend this country, and scores and scores of their colleagues were being lynched for doing nothing other than being African American. Right? It we solved a lot of the problems with this. No, this, and that was a, believe it or not. At the same time, all these African Americans are enlisting to defend the country. In World War ii, Congress couldn’t even get a law passed. anti-lynching law passed. So the

ALEX POWELL: Yeah.

C. EVAN STEWART: didn’t, didn’t solve all those problems and make everything hunky dory. So let, let’s not kid ourselves here and get on a high horse about this, that, and the other thing, and say, oh, the Civil War was, and the, the only other thing I would mention is people don’t recognize or realizes we’re the only country had slavery that solved that problem by a civil war. So the notion that the Civil War was quote inevitable, uh, I’m not so sure. We should just blindly assume that’s right. we’re the only country that had a civil war to get rid of it. Maybe a civil war was necessary to get rid of it. I don’t know. To say it was inevitable. I’m not sure I agree with that either. ’cause that wasn’t true with the British Empire. Lots of other places that got rid of slavery. So let’s be, so there’s the, let’s not deal with the what ifs, but let’s not also say things were inevitable or this had to happen. That’s not history, either. History of a lot of serendipitous events, a lot of things, uh, that happened and then this cause of that to happen, this cause to happen.

Then some, I mean, look at how World War I happened. No one could possibly have predicted that the assassination of the Archduke would’ve led to the, to that point, the worst war in, in a human, human history to be only dwarfed by World War ii. No, no one could possibly have predicted that that assassination would’ve caused World War I.

ALEX POWELL: The slings and arrows of outrageous fortune or fate. Uh, you know, it, it’s, uh, it, it’s such an important perspective to offer because we’re inundated with the rhetoric that it was inevitable. The Civil War was inevitable, you know, ever, ever since we had social studies in, in grade school.

C. EVAN STEWART: Yeah.

ALEX POWELL: it, it, it’s, it’s very important to have that perspective.

Um, and also, uh, you know, Lincoln, of course, who, who was like, like you, like you say, um, when we talked about off air, our greatest president, but he, he wasn’t, he wasn’t a god, he wasn’t an angel. Uh, so I, I, it’s. I appreciate the perspective and I’m excited to do, uh, a deep dive, not into, not only into this, this book Evan, but also into, uh, your writing more generally.

Uh, um, I know you have a book about the worst Supreme Court decisions and, uh, Myron Taylor, who was FDRs back channel to, uh, the Vatican during World War ii and very, very interesting points about how the Civil War didn’t, didn’t solve. The treatment of African Americans, of black people within America. Far from it.

Uh, I think about my grandfather, Theodore Powell, who was the deputy mayor of, uh, Manchester, Connecticut. I know that you’re in Connecticut now. He, um, in World War ii, uh, fought in the Battle of the Bulge and helped to liberate concentration camp at, at Dachau. Uh, and then 20 years later, he went to Selma, uh, to March for Civil Rights in 1964, I believe.

And that was, you know, a hundred years later after the events you’re describing and, and this book. Um, so this has been a fascinating discussion. Evan, uh, I know that you have a website. I believe it’s C. Evan Stewart.com. Um, where else can people find out about, about your work?

C. EVAN STEWART: So the website, uh, which is, uh, set up by my daughter ’cause she’s much more technologically savvy than I am, is C. Evan Stewart author.com

ALEX POWELL: Got it.

C. EVAN STEWART: and, uh, that has, uh, information about, uh, all four books and, um, uh, has other links to, uh, other hopefully when you go live, we’ll put up on the, on the website if

ALEX POWELL: I’ll put all of it in the description.

C. EVAN STEWART: that for me. and, uh, just information more generally and stuff like that. And then how to get the books. So, uh, all that information is there and so it’s a. really did a very nice job, very thankful. And, uh, so that’s, that’s the best way to go C. Evan Stewart author.com.

ALEX POWELL: C. Evan Stewart author.com, and the latest book is William Henry Seward’s Quest to Save the Nation during this secession winter. Uh, it’s available now to purchase, uh, Evan, thank you very much for your time today on Cited Authorities.

C. EVAN STEWART: My pleasure, Alex, the real pleasure. Thank you so much.