Home » News » Beyond the Law: Fighting for Liberty When Justice Fails with Diana Simpson

Beyond the Law: Fighting for Liberty When Justice Fails with Diana Simpson


Our nation’s constitution serves to protect innocent people from punishment…but what happens when legal precedent and case law run contrary to that notion? This week Diana Simpson joins host Roger Ream to discuss her work in promoting economic liberty and protecting individual rights, fighting against government infringements, and the important mission of creating legal precedent to expand liberty. Plus, a look at some of Diana’s current cases and why storytelling is such a critical aspect of building a legal case.

Diana is an attorney at the Institute for Justice, joining the law firm in 2013 after working as a constitutional law fellow. She’s also an alumna of TFAS’s 2009 summer law program, where she currently serves on the Board of Visitors for TFAS’s Law Fellowship. Simpson litigates cases to promote economic liberty and protect both private property and free speech. She specializes in fighting against irrational zoning decisions and abusive fines and fees practices.

Currently, she is the lead attorney in a class action lawsuit against the City of Chicago, which imposes excessive fines and harsh fees on tens of thousands of Chicago residents and visitors each year. Her work has been featured in numerous outlets including The Economist, The Wall Street Journal, National Public Radio’s 1A and The New York Times.

Episode Transcript

The transcript below is lightly edited for clarity.

Roger Ream [00:00:02] Welcome to the Liberty + Leadership Podcast, a conversation with TFAS alumni, faculty, and friends who are making an impact today. I’m your host, Roger Ream. Today, I’m excited to welcome Diana Simpson to the Liberty and Leadership Podcast. Diana is an attorney at the Institute for Justice, joining the law firm in 2013 after working as a constitutional law fellow. We are proud to call Diana an alumna of our 2009 Summer Law Fellows program. Diana litigates cases that promote economic liberty and protect both private property and free speech. She specializes in fighting against irrational zoning decisions, abuse of fines and fees, and other government infringements on individual liberty. Currently, Diana is the lead attorney in a class action lawsuit against the city of Chicago, which imposes excessive fines and harsh fees on tens of thousands of Chicago residents and visitors every year. Diana’s work has been featured in numerous media outlets, including The Economist, The Wall Street Journal, National Public Radio and The New York Times. Diana, it’s wonderful to speak to you today about your important work. Welcome to the Liberty and Leadership Podcast.  

Diana Simpson [00:01:31] Thank you so much. Thanks for having me.  

Roger Ream [00:01:32] I’m excited about the chance to talk to you because you’re involved in so many important and interesting things, Diana. Can I begin just by asking you to give us a little background on yourself, where you grew up and where you got your education?  

Diana Simpson [00:01:46] So, I grew up in Colorado, in a town just south of Denver, and I came out to the East Coast for school and basically most things since then. I went to Sweet Briar College in southern Virginia for my undergrad, and then I went straight through from college through to law school. I went up to Roger Williams University in Rhode Island for law school. And then my first summer in law school, I participated with The Fund for American Studies and had a fantastic time in D.C., and then my second summer, I went out to Arizona, which may be the worst time to be in Arizona is the summer, but it was a wonderful experience. I got to work at the Institute for Justice, which had been kind of my dream organization for a long time, and I was able to spend the summer there, and then after I graduated, I was able to get a fellowship at IJ, in the Arizona office. So, I was there for about a year and a half, and then joined our headquarters office in Virginia, kind of at the end of 2013, I guess that was. And then, moved out from Arizona to Virginia, and I’ve been here ever since.  

Roger Ream [00:02:53] When you were in Arizona, did you have the opportunity to meet, a fellow TFAS alum, who helped found the Institute for justice, Clint Bolick?  

Diana Simpson [00:03:02] I sure did. He was at Goldwater at the time. This was before he became an Arizona Supreme Court Justice. He is just such a delight. He’s so wonderful to talk to, and he’s been so monumental in so many different legal movements, really.  

Roger Ream [00:03:16] Yeah, he’s one of those people I consider a poster child for The Fund for American Studies, because when he came to our program from Drew University, he tells me now that he had taken one economics course and hated it and had no interest in the law. And then at TFAS, he had economics with our longtime professor George Viksnins, and that lit a spark in him that interest some in economics, and we had him interned for Senator Orrin Hatch on the Judiciary Committee. So, he gained a love for law, and he’s done some remarkable things in his career and continues to accept invitations we send his way to come speak at events. So, we’re grateful for all that Clint does. What got you interested in the legal profession?  

Diana Simpson [00:03:58] So, a case came out when I was in undergrad called Kelo v. New London, and long story short, a lovely woman named Suzette Kelo had her house, basically threatened by eminent domain from her city because they wanted to use the land that it was on, to give to Pfizer, so that Pfizer could then develop a plant and have housing for a bunch of its staff, and so on and so forth. And it was this private to private, taking and giving, and Susette Kelo was going to have to pay the burden of it. The Supreme Court said that that was perfectly acceptable under eminent domain, that that was that was an acceptable use of the power and that the Takings Clause of the United States Constitution didn’t prohibit that. So, at the time, I didn’t necessarily understand all the legal reasoning, but I was so upset by what had happened, it didn’t jive with any understanding that I had of what our Constitution is meant to do, and what the system is supposed to do, that I was just outraged and said: “You know what? I think law school really might be a good place for me. I’d like to fight against things like that. I know there are good people out there fighting against this, and I’d like to join up with them.” So, I’ve basically had IJ in my, in my kind of long-term vision for a long time. I’s been wonderful going from seeing Kelo on the outside to meeting Susette and working on it from the inside.  

Roger Ream [00:05:26] I would agree with you. I think it was one of top ten worst decisions in the last hundred years by the Supreme Court. It seemed clearly, a decision that should have gone the other way, but it didn’t. Has anything been done since then to help rectify the situation with regard to private takings for private purposes?  

Diana Simpson [00:05:49] So, it’s one of the things that I absolutely love about IJ is that it lost the Kelo battle, right? We lost at the Supreme Court in a really, I think, devastating fashion, and the organization didn’t take it kind of sitting down. They went and basically employed their activism team and went across the country trying to make it harder for governments to use eminent domain. And today, I think we’re up to 47 states have made it more difficult to use eminent domain than the decision under Kelo would allow you. And so, whether that’s through legislation or through state court decisions, under the state constitutions, it’s now harder. Of course, Kelo it’s still out there, and I think we’d still like to see it overturned. It was wrong when it was decided, and it’s wrong today. So, it would be wonderful if the Supreme Court would correct its error. We’re certainly on the warpath trying to find an opportunity to do it, but most states, I think, have learned their lesson and are trying other things to take people’s property so that it’s perhaps less, in the limelight in a negative way for them.  

Roger Ream [00:06:58] And Mrs. Kelo, I assume, lost her pink house and there’s now a Pfizer property there instead?  

Diana Simpson [00:07:04] There’s not. The Pfizer development squandered. It never came to fruition, and last I heard, there were some feral cats living on the property. Her house, they moved it, it’s gone, but that spot that she had is is gone, too.  

Roger Ream [00:07:19] That’s just even makes the story worse when you hear that they never even built the development they plan to build there. So, that inspired you to this career you followed? In what way did the TFAS Law Fellows program you attended contribute to it as well, while you were in law school?  

Diana Simpson [00:07:37] That was such a wonderful experience for me. So, it was my first year or my first summer after, I guess, the summer after my first year of law school, before my second year, we took a class with Nadine Strawson and John Baker on originalism, and it was so wonderful hearing the two of them. I mean, they’re just really lions of the profession. It was great learning from them. And then, of course, TFAS brought in all these different other speakers to talk about different facets of the legal world, whether the for-profit world or the nonprofit world, the political realm, activism, all the different ways in which you can use your law degree. That was great. On top of that, I had this wonderful placement. I was at a think tank in Georgetown, working on basically public policy all the time, and that was just fun. I loved all the folks that I got to work with. I’m still friends with some of them, either who I worked with or who I met through the TFAS summer program with me. And that’s been 15 years now, and there’s a few of us who are still chatting, and it’s just really been wonderful.  

Roger Ream [00:08:48] I do want to talk about some of the cases that you have worked on and perhaps are working on now, but first, could you describe for people that might not be familiar with Institute for Justice, what its mission is and what its focus is? 

Diana Simpson [00:09:02] Yes. So, at the Institute for Justice, we’re a nonprofit law firm. We represent our clients for free. And we’re out to basically make the United States a place that is more responsive to the Constitution and protects individual rights. So, we do this by operating in what we call the four pillars. So, property rights, free speech, economic liberty and educational choice. We think that those are what make up a free society and let people live the life that they want to live without unnecessary government interference. And so, we do that through litigation, but also through our other teams at IJ. So, we have an activism team who I’ve already mentioned, and they go out and they build grassroots activists across the country, who can then fight for change, not just in courtrooms, but in legislatures and town halls. We have a strategic research team who works on all the data, the numbers and the nitty gritty that are very important for making the cause for change. And, we also have our communications team, and they play a critical role. So, I think a lot of people are familiar with Suzette Kelo’s story, and that’s a large part because of our communications team. They work with Suzette, they tell her story, they have her tell her story. A lot of lawyers, I think, you see out there saying: “Oh, no comment,” when media comes up to ask them, and we’re the exact opposite. Our clients all have very compelling stories, and what happened to them, it’s either the government has done something bad, or the government won’t let them do something that they have a constitutional right to do. So, they’re the ones out telling their stories and about what’s going on has impacted them and why the Constitution should step in and help them. And so, we have a couple other internal teams, but that’s how we do it. We get out and we have our clients telling their stories and we’re out actively fighting for them. We litigate our cases in the court of law and the court of public opinion is how we describe it.  

Roger Ream [00:11:00] We had another graduate of our program work at IJ for some time, Melanie Bennett. I don’t know if you overlapped with her, but I recall she would send me a video testifying before the New York City Council about economic liberties, and I thought: “Wow, that’s going into the trenches.” 

Diana Simpson [00:11:15] Melanie is wonderful. She was part of our activism team, and she is just such a firecracker. It was just so great at going and talking to a group of people and getting them excited about their rights in a way that I think a lot of people don’t always assume that they have the ability to do that and to fight for it.  

Roger Ream [00:11:33] It seems like many of the cases I’m familiar with that IJ has taken on involve minorities, involve people on the lower ends of the economic ladder. I remember one of your first cases was a shoeshine business in Washington, D.C., Ego Brown. And then there was case of funeral directors in, I think, Louisiana, who are mostly African Americans, I think, wanting to sell caskets and were being opposed by the funeral industry and cases like that. Do you find that a lot of the cases you take on involve, well, even immigrants, but people who otherwise wouldn’t have the any opportunities?  

Diana Simpson [00:12:16] Yes. So, most of our stories are these David and Goliath stories where the government has come down and they’re working to protect the interests of a very favored group of people, and that means pushing out the less favored group of people, and because of kind of the social dynamics of this country that often involves different groups of people based on what they look like or where they’re from. It’s really frustrating to see. You’ll see, with a lot of our economic liberty work, for example, will have people who are trying to be entrepreneurs for the first time. I’m representing a mechanic right now in Texas who’s a first generation American. He and his family moved here from Mexico, and he’s been an American citizen for decades and he’s just trying to open his mechanic shop, and the city won’t let him. We don’t have a racial claim in the case. Our case is just about property rights, but that’s kind of a quintessential entrepreneur. He’s got this great American story, and we love to sit there with him and tell it while we’re fighting for his rights, to open up.  

Roger Ream [00:13:20] If you can talk about some other cases. You’ve got one in Arizona, I know, involving a woman, Norma Thornton. Can you talk about that case?  

Diana Simpson [00:13:27] Yeah, I’d be happy to. So, we represent Norma Thornton. She’s a retired grandmother. She worked in food service for many years. She dabbled in a bunch of different things. And so, she was living up in Alaska for most of her adult life, and then when she and her husband retired, they moved down to Arizona. When she had been in Alaska, one of the things that was an important part of her life was giving back to people who were in need. She ran a restaurant, she owned a restaurant and would feed the people who were paying customers, but she would also be sure to save some food for people who didn’t have the ability to pay. This was something that was very important. She herself grew up in poverty, so she knew what it was like and didn’t want others to experience that. So, they retired, they left Alaska, they went to Arizona, and she wanted to keep doing that. So, she got involved with the community in her city, it’s called Bullhead City. It’s about an hour and a half outside of Las Vegas. She started serving food to people who were hungry. She would just go home and make the food. She knew how to make food, probably better than anybody. She would go home and make these big trays of food and go out and serve people who were hungry. That just gave her a lot of meaning, a lot of joy, so she’s been doing that for about four days a week. The city, one day, police officer came in and arrested her, and she had no idea what was going on. Like, why are you arresting me? It was because the city had recently passed a requirement that you get a permit in order to feed the hungry on public property, but this permit is basically impossible to get. There’s no way Norma could get it, and she didn’t have one. She didn’t know that she needed one. And so, like I said, they arrested her, they charged her, they ended up dropping the charges when they realized that this probably wasn’t the best idea to charge a grandmother for feeding people who are hungry. But that didn’t end it, as she still wants to feed these folks. So, she’s currently feeding them in a small, little private alleyway, but that’s not enough. She had been feeding in the park. That’s where people are. They’re allowed to be there, and so why can’t she use the park? The park is perfectly set up for this, and the way the laws written, if she were feeding her friends, if she was having a pizza party for her friends, for her family reunion or something like that, she could still serve. It’s just because she’s feeding this population that she can’t do it. So, we filed this case on her behalf, and we’re currently waiting for the judge’s decision. We’ve fully briefed it, and our argument here is that the Constitution protects the ability of people to use their own resources to help others. There’s a lot of questions about kind of how to serve those in need and what the best way for the country moving forward could be, but this is certainly one component of it, is to let charities and to let charitable individuals help other people rather than arrest them and say: “Well, you can’t do this. You need to go away.” And so, like you said, we’re in the middle of the case. We’re waiting for a decision from the court now and we’re just overjoyed to represent Norma. It’s an honor to represent her, and it’s deeply frustrating that she had to get arrested in order to do this.  

Roger Ream [00:16:53] I imagine in many cities, of course, government provides food for homeless people, and one thing we know is government doesn’t like competition. Maybe that’s why they want to shut down a charitable act by this wonderful woman. Well, we’ll be interesting to hear more. I guess, the decision will come any day now or any month? 

Diana Simpson [00:17:12] We’ll see. It’s all up to the court, but I’ll hopefully soon.  

Roger Ream [00:17:15] There’s some other interesting cases that you’re involved in right now that you can talk about?  

Diana Simpson [00:17:19] Right now, I’m litigating a case in Chicago about it impound program. So, Chicago basically impound cars for about two dozen reasons and the owner has to pay a fine if it was impounded for a particular crime or other offense underneath the code. So, to get the car back, they have to pay this big fine and in whatever fees have accumulated. So, we represent a couple of people who didn’t have a lot of money, they had absolutely nothing to do with the underlying crime. So, for example, one of our clients lent his car to a friend, his friend was pulled over and they found out that his license had been suspended. Well, he had no idea. Our client obviously had no idea. And yet the city said: “If you want to get your car out, you have to pay $3,000 in fines plus the towing fee, plus all the storage fees.” He’s retired, he’s living on a limited income, and he just didn’t have the money for that. And he said: “Well, I didn’t do anything. Can I get my car back?” And they said: “Sure, if you pay us thousands of dollars.” And he was like: “Well, I can’t afford it. What am I supposed to do?” And they said: “Well, you’re going to lose your car.” And so, he did. He lost his car. This isn’t right. This isn’t right under a few different provisions of the Constitution, both the U.S. Constitution and the Illinois Constitution. And so, we’ve sued and we’re in the middle of that litigation right now. I hope that we prevail. It’s just very un-American to charge people for the crimes of somebody else, particularly in a circumstance when they don’t even know what’s happened.  

Roger Ream [00:18:55] Do you have, kind of a process where, when you’re considering a case, you obviously have lots of opportunities to take on a case that has someone being mistreated by government. Do you try to look for cases that, in a sense, set a precedent you can build on or establish a precedent in an area where it’s really needed?  

Diana Simpson [00:19:19] Absolutely. So, unfortunately, in the business of suing the government when they violate people’s rights, business is booming. And that’s not a great place to always be, but we’re out there trying to find clients and trying to find cases that we think can create this big precedent. So, institutionally, we’ve had two big cases at the Supreme Court this term, one about representing people who the government has taken property from them, and then the government says they’re immune from a lawsuit trying to get compensation for the taking. That’s not right. The Supreme Court said: “No, no, don’t go back to State court. You have to actually be responsible for this.” So, things like that. We’re always trying to build precedent. We’re always trying to create this kind of situation. I mean, in Chicago, that impact program impacts tens of thousands of people each year, and there are untold numbers of people who are innocent who had nothing to do with it. So, what we’re looking to do is create precedent that says the Constitution protects innocent people from punishment. It’s such an obvious proposition, it shouldn’t have to be litigated, but there’s a lot of case law saying the opposite, and that can’t be the case. So, we’re here, we’re fighting, and we’re trying to represent these folks and get a ruling that says this kind of common-sense proposition that really aligns with the historical understanding of the Constitution.  

Roger Ream [00:20:39] Do most cases that you take on initially, I guess, start in state courts?  

Diana Simpson [00:20:45] It really depends. It depends on kind of what our goal is, what our claims are. So, sometimes we litigate in state court because there’s a particular state constitutional provision we’re excited about, sometimes we litigate in federal court because there’s a federal constitution, a provision that we’re excited about, and we think we can make broader precedent in federal court or perhaps we make broader precedent in state court. It really depends on the case, and we evaluate at each time. I don’t think there’s one that’s necessarily better than the other. It’s just for a particular case, and what are our goals and where we go from there.  

Roger Ream [00:21:20] Does IJ find that there are a healthy number of young people coming out of law schools that are interested in public interest law, particularly as it relates to economic liberties, property rights, free speech, the kinds of things you work on there?  

Diana Simpson [00:21:36] There are. It’s really heartening. I think there are lots of reasons to be cynical or pessimistic, when you watch the news, or you look out on the world today and I try not to do that.  

Roger Ream [00:21:46] Or when you see what’s going on in so many law schools, that’s a little depressing.  

Diana Simpson [00:21:50] Oh my gosh, yes. It’s devastating to see, and I try not to because there’s so many reasons to be optimistic. There are so many opportunities for us to go forward and make this good case law and make these good precedents that can then expand liberty rather than contract it. So, we have a summer program of law students who come in every year, and they spend usually about ten weeks with us. They’re all so enthusiastic and optimistic. It’s great. They’re bright and sharp, and it’s great seeing them, knowing that they’re about to go out into the world and be lawyers themselves. Some of them stay with IJ, some of them stay within the public interest movement generally, some of them, they’ll go into the to the private kind of for-profit world for a bit and then they come back, and that’s great, too. There’s a lot of opportunities for folks to make an impact here, but it’s always great getting to see the different students and seeing how enthusiastic they are.  

Roger Ream [00:22:52] IJ’s clients generally do have very compelling stories that you can tell. As someone who’s now involved in the law, as you have been for a number of years, is knowing the law, well, that’s very important. Is the story telling aspect of this an important part of what you do?  

Diana Simpson [00:23:12] It’s critical. Judges are people, too. So, they are moved by the same kinds of things that most people are moved by. When we have a story about Norma, we put out a video when we launched her case that included the bodycam footage of her being arrested, and that’s powerful video to see. Her story is a powerful one. She chokes up often when she tells it, I choke up sometimes when I tell it, because what she’s gone through in her life and where she is now and in this fight that she’s willing to have when she’s retired, she’s 80 years old, and she’s willing to stand up for what’s right because it’s right. That’s a really important component of it and we have to convince the judge of that too. Now, it’s not always enough. Suzette Kelo had an extremely sympathetic story, and yet she lost, but it’s a necessary component of really getting the success, I think. It’s hard to represent somebody who is not sympathetic, but it’s really easy to represent someone who’s a lot more sympathetic, and you’re willing to stand there with them and vindicate their rights.  

Roger Ream [00:24:23] That video you referenced in, can it be found at IJ.org, at your website?  

Diana Simpson [00:24:27] It sure can.  

Roger Ream [00:24:28] Good. I’m to encourage people to watch that, and I’m going to certainly do that. I’ll some tissues nearby in case I start to tear up, which I probably will. I wanted to ask you, go back to the law fellowship for a minute that you attended at TFAS because, afterwards, I know you have been involved in our Board of Visitors, have been very helpful to the program itself. Can you comment on kinds of things you do as a member of the Board of Visitors?  

Diana Simpson [00:24:59] Yes. So, we come together a couple times a year and we talk about the summer program, and what they’ve done in this last year, what they’re expecting to do next year, the different kind of speakers that are brought in, the educational component they get, and the students who come in. It’s so wonderful. I talk about the IJ students that we see every summer, but I’ve been able to talk with the TFAS Law program students for the past several summers. I don’t even know how many at this point. And it’s so much fun every summer because they’re so enthusiastic and they’re just such a bright group of students. It’s great to see them and to see their resumes and to see what they’re going to go off and do. It’s exciting.  

Roger Ream [00:25:41] I know you spoke, just a few weeks ago to this year’s class of law fellows. I should mention for people listening that while they’re with us, not only are they doing some sort of internship or associateship or clerkship, but they’re taking courses through the Scalia Law School, one in law and economics, because we think understanding economics is important, and the other in originalism. That gives them, I think, a take on those subjects that isn’t one they would typically get at most law schools. So, we try to supplement their legal education through those courses, especially the one on originalism, but also on economics. So, it’s been a evolving program. It’s changed a lot since you attended in 2009, I think, for the better, but your help as a member of the Board of Visitors has helped him improve that program. I think one value, too, that you touched on earlier is the network it creates among the fellows. So, thank you for your involvement in that.  

Roger Ream [00:26:43] This is a question you don’t have to answer, but do you have kind of a proudest moment in terms of your work at IJ, a case that you’ve been working on that reminds you of what motivated you to get into this field?  

Diana Simpson [00:26:57] There have been quite a few over the years, but there’s one in particular, this is from last year. It’s recent. We represented a homeless shelter in North Carolina, in small little town called North Wilkesboro, North Carolina. And the town, basically wouldn’t let the shelter open. The shelter had been operating for about 30 years at one location and kind of gotten grandfathered into the zoning code, but they found they needed a bigger space and a slightly better one. So, they got a donation from a local dentist that checked off all the boxes, that met every single requirement under the zoning code. So, they were excited, and they said: “Great, this will be no problem.” It wasn’t no problem. The town wouldn’t let them open, for some spurious reasons. They said that it was dangerous because it was next to a highway with the sidewalk, despite the fact that the zoning code required it to be in the highway business district with the sidewalk, and a couple other things. They also said it wasn’t harmonious with the area, and that it would reduce property values of the neighboring properties, and which didn’t make a lot of sense because this particular location it was in, it was near the social services that are available in town. It was near a bunch of fast-food restaurants. It was not in a residential area at all. Like it was really kind of where you would want a homeless shelter to be, recognizing that, of course, no one should be homeless and that in an ideal world there wouldn’t be a need for a homeless shelter. But if there is one, if there is that kind of a need, then the governments need to get out of the way of people who are looking to provide them. So, we sued, this violated the equal Protection clause of the United States Constitution, and we won. It was a wonderful win. It was so exciting. Last August, I was able to go down there for the grand opening. They finally did the renovation, and they had their big grand opening. We had one of those big red ribbon cuttings and everything and it was a wonderful moment for me. It wasn’t even really about me. It was this wonderful moment for the neediest people in this county who now have a spot that is perfectly situated to their needs. It’s right where they need it to be, and the Constitution protected their ability to do that. I think, of recent times, that was perhaps one of my favorite moments, was being down there for that big opening.  

Roger Ream [00:29:15] Well, I can see why that was a moment of great pride for you. In most cases, do just clients come to you, or do you guys have a process of trying to find clients with good, important causes to support?  

Diana Simpson [00:29:30] Yeah. So, that’s a good question. It’s some of both. Because we’re a nonprofit, we’re allowed to contact potential clients in a way that most lawyers are not. We don’t have any kind of financial interest in their case and in representing them. So, I’m allowed to read a story online and say: “This is outrageous,” and give that person a phone call, in a way that a lot of attorneys can’t. So, that North Carolina case I just mentioned, I found out about it through a Google alert, and it came through on my inbox and I saw it and I was like: “Well, this is something that’s not quite right.” We were on the phone with them almost immediately. There are other circumstances where we get a potential client form, people can submit them on our website, and it’s a situation that looks like an area we might be able to help. So, we look into it, and we dig into it. Sometimes, there’s a particular precedent that we want to attack, or we want to expand. So, we theorize, and we brainstorm what the best way to get there is, and then we go find clients in that particular circumstance and try to find more folks and then represent them. So, sometimes that’s through public records requests, sometimes that’s just standing on the ground outside of a particular government meeting and trying to get people to sign up and talk to them right then. It can take on a lot of different ways that we do it, and can look a lot differently based on each situation, but there’s a few different ways, I suppose.  

Roger Ream [00:30:54] When you go into court to defend a client, or to take his case, to what extent do you think the judge assigned to the case is going to impact the outcome? Do you think no matter who that judge is and what their record is and what their politics might be, if you even know that, but does that set such a high obstacle to you that you from the start think: “Oh, this is going to be really tough to win,” but maybe you’re trying to establish a record that can be used on appeal? How does that enter into this?  

Diana Simpson [00:31:27] It certainly plays a role. I think thinking long term is the best kind of antidote to that, because sometimes you’ll be in front of a trial court judge and they’re not going your way, and you know, they’re not going your way, but they’re not going to be the final decision maker. So, you just kind of grit your teeth and you get through it. You build the record that you want to build, and you do everything you can to get to the next phase. And then sometimes the next phase isn’t necessarily what you would have anticipated or what you would have preferred. You grit your teeth and you try to go to the next phase, and you just always try to keep going because there are things you can control in litigation, and that’s what you put into it, right? You can’t control what comes out of it, necessarily, but you can control what goes in. So, learning your lessons and figuring out what worked last time, what didn’t work last time, what documents do I need in the record? What questions do I need to ask at a particular deposition? To really get into the nitty gritty. Like those kinds of things you can control, and then from there you can’t. You put together the best briefs you can and say: “I hope that’s enough, and then you go from there and you prepare as much as you can for oral argument and hope that it’s enough. But then you just have to keep thinking about what’s next and try not to get bogged down in the material that you can’t control and say: “All right, how are we going to fix this going forward? How are we going to get to the ultimate win that we’re seeking?” 

Roger Ream [00:32:51] What kind of advice would you offer to the next generation of lawyers, to the law students who talk to at TFAS and elsewhere about how to be effective at fighting for liberty in their careers? 

Diana Simpson [00:33:04] Be unrelentingly optimistic. I know that I said it’s easy to get pessimistic. We live in a really wonderful country with a wonderful constitution in both at the federal level and in each of the states, and there’s so many opportunities to mold the country in a way that you see fit, and particularly for people who are listening to this, in the way that’s right. There are so many different opportunities to pursue that you just have to be optimistic and be creative. Don’t get tired, don’t get beaten down by it. Just say: “You know what? That was a bad day. What’s up tomorrow?” That served me well over the years. I certainly don’t win every case. I haven’t won every case. Losing is a really unfortunate part of litigation, particularly, when you’re representing people who are really sympathetic and have these wonderful stories. The worst phone call to make is the phone call to the client to say that we’ve lost, but being able to say we’ve lost, but here’s what’s next, takes the sting out a little bit, both for them and for me as well. Being able to say: “Okay, this isn’t the end of the road.” So, I try to have that mantra in my head no matter what, it isn’t the end of the road, and we can continue to march on onward until we get to a place where the world kind of reflects a little bit more liberty and a little bit more freedom for people.  

Roger Ream [00:34:31] Wonderful. That’s a great approach, and I think that’s a good note to conclude on us. It looks like we’re running out of time. Thank you so much for joining me today, Diana. It’s been great to have some of your time. I’ll yield Bressler back to you to go fight for liberty for another person somewhere in this country that needs your help. Thank you so much.  

Diana Simpson [00:34:50] Thank you so much, Roger. I appreciate it.  

Roger Ream [00:34:52] It’s been a pleasure.  

Roger Ream [00:34:55] Thank you for listening to the Liberty + Leadership Podcast. If you have a comment or question, please drop us an email at podcast@TFAS.org and be sure to subscribe to the show on your favorite podcast app and leave a five-star review. Liberty + Leadership is produced at Podville Media. I’m your host, Roger Ream and until next time, show courage in things large and small.  


TFAS has reached more than 49,000 students and professionals through academic programs, fellowships and seminars. Representing more than 140 countries, TFAS alumni are courageous leaders throughout the world forging careers in politics, government, public policy, business, philanthropy, law and the media.

Liberty + Leadership is a conversation with TFAS alumni, faculty and friends who are making a real impact. Hosted by TFAS President Roger Ream ’76, the podcast covers guests’ experiences, career stories and leadership journeys. 

If you have a comment or question for the show, please email podcast@TFAS.org.

View future episodes and subscribe at TFAS.org/podcast.


Recent Posts


Beyond the Law: Fighting for Liberty When Justice Fails with Diana Simpson

This week, another exceptional TFAS alumna joins us on the Liberty + Leadership Podcast: Diana Simpson, 2009 TFAS alumna and attorney.

Gary and Aldona Robbins Scholarship Established for Economic Education

The Gary and Aldona Robbins Scholarship at TFAS was established in 2024 to honor the work of a husband and wife who together made outstanding contributions to the field of economic policy. Upon Aldona’s passing in May, TFAS regent and friend of Aldona,…

Maintaining Our Republic: Mitch Daniels Delivers Annual Neal B. Freeman Lecture

The 2024 cohort of D.C. Academic Internship Program participants welcomed former Indiana Governor Mitch Daniels at George Mason University for this year’s annual Neal B. Freeman All-Student Lecture on June 11.