Practicing Unhappy Law
Bankruptcy lawyer Cynthia F. Grimes doesn’t practice happy law, but she’s perfectly content with that
Published in 2012 Missouri & Kansas Super Lawyers magazine
on October 15, 2012
Updated on May 27, 2022
Q: What brought you to the law?
A: My parents were teachers. This was in the ‘60s, and a lot of change was happening in education, and my father in particular was unhappy with the direction of education, and so he just quit and went to night law school. I think I became aware of what he did as a lawyer when I was 11 or 12, and just instantly decided that that’s what I was going to do, too.
Q: Did your father’s approach rub off on you?
A: I think it did. My father and I talk about this a lot: that what you do and how you interact and how you get along with people in the law is more than an occupation. It’s a profession, and it’s a way of life. I had an advantage because I was able to see from my father how you’re supposed to do that.
[Early in my career] I was assigned to second chair at a trial. It was the bankruptcy court in Kansas City [Kansas]. I got to the trial and the lawyers on the other side were male lawyers and they had a young female associate, and it was icing and snowing and raining, and they had gone into the courtroom and they had asked her to bring in all the boxes of evidence. And she was pregnant and struggling on the slope in high heels, because of course we couldn’t wear pants … everyone was afraid to wear pants to court so all the women wore dresses. So she’s struggling in these high heels so I helped her. And a lawyer from my own side said, “You can’t do that. You’re helping the enemy.” And I said, “You know what? She is not our enemy. Her client is not our enemy. She’s our opposing counsel.” That’s really when it hit me that if we want to aspire to have the law as a profession, we can’t treat other lawyers and clients that way. It’s just not right. I blame law school in the sense that it didn’t really address how you behave as a lawyer. But I knew from watching my father interact with lawyers, and watching him try cases, that the other lawyer is not your enemy.
Q: You blame law school. Does that mean you didn’t enjoy it?
A: I hated law school. Hated! I think a lot of lawyers, if you ask them honestly, would tell you privately they hated law school. I don’t know many people who enjoyed it. Because I always knew I was going to be a lawyer, I decided to pick a major that would be interesting and completely different from law. I majored in French and art history. I loved undergrad. I studied abroad in France for a year; I took this broad variety of liberal arts classes: ancient accelerated Greek, computer science, astronomy. … I took one pre-law class and actually didn’t do very well in it, but I wasn’t worried about that because I knew I was going to be a lawyer. So I got to law school, and I thought it was not very intellectually challenging. I thought it put a lot of emphasis on rote memorization. I thought it was competitive and cutthroat.
Q: Did you consider dropping out?
A: I actually got a call somewhere around my finals my first year from my art history professor, who said, “Please, please drop out, I can get you a full-ride Mellon Scholarship to get your Ph.D in art history.” She said, “You are the best art history student I’ve ever seen.” Well … I was tempted. I was really tempted. I just couldn’t see then what I was going to do as a lawyer.
Q: When did you start to visualize what you would do as a lawyer?
A: It was very interesting. This was a time when women were just beginning to come out of law school in bigger numbers. I think about one-third to 40 percent of our law class was women. I was pregnant. I had gotten married two days before law school started, and I interviewed when I was pregnant with many of the big firms downtown in Kansas City [Kansas]. I was asked questions like, “Does your husband know you’re here? You can’t possibly think you can be a lawyer and a mother at the same time. Why should we hire you when you’ll obviously quit as soon as you have the baby?” Amazing. I mean, amazing, amazing questions. I was really discouraged. Right up to the point I graduated, I didn’t have a job. I applied to be a judge’s law clerk with Judge John Rees of the Kansas Court of Appeals, and he looked at me and said, “I never, ever, ever, in my wildest imagination—ever imagined I’d have a woman work for me!” and I thought, Oh no, the interview is over and I haven’t got a job. What am I going to do? Then he looked at me and barked, “Well are you going to take the job or not?” So I started out as a Kansas Court of Appeals law clerk. It was a great, great job.
Judge Rees was a great judge. He approached everything from the point of view of, “Let’s start at ground zero. Make no assumptions. Why is this appeal even before us? What power do we have to do this? Why was this case even filed?” It was a great background because it allowed me to see so many different types of cases: divorce, criminal, oil and gas, probate. I got to learn a lot about a whole lot of different areas. I did that for two years, and then my husband at that time decided not only did he want to finish his engineering degree, he wanted to go on and get a master’s. [The plan was] he’d get his master’s, I’d get another clerkship, we’d finish up the same time, and then we’d burst onto the world together. I was still thinking, at the time, that I would be a back-office, mild-mannered, “I’ll do the work,” kind of quiet lawyer.
Q: But that’s not the lawyer you became.
A: [Laughs] No! You know, I think it had to do with finding bankruptcy. Once I fell into it, my goal was to be a star. And there is no way to be a star in the back office. You’ve got to get out there and you’ve got to do things and try cases and develop your own clients and start your own firm if you want to be a star. That’s what I did. I mentor a lot of young lawyers and law students, and when I go talk to them, I tell them … don’t rule anything out. Because however you see yourself, you might be convinced you’re going to be a criminal lawyer, but until you get out there and do it, you don’t know. If someone had said to me 25 years ago, “Cynthia, you’re going to be a rainmaker and recognized by peers and have your own business, and considered a dean of the bankruptcy bar. … Golly. I never would have imagined any of it.
Q: How did you fall into bankruptcy?
A: After my [appeals] clerkship ended, my father said, “Why don’t you apply with [bankruptcy] Judge [James A.] Pusateri?” So I applied for a law clerk position, and I said, “Judge, I don’t know anything about bankruptcy. I never took a course, I don’t know anything about it.” And he said, “Well, Cynthia, if you know how to write an opinion, you can fake the bankruptcy part. And if you know about bankruptcy, you can fake the opinion-writing part. You just can’t fake both.” And I got the job and immediately, immediately, fell in love with everything that was bankruptcy.
Q: What about it speaks to you?
A: It is very intellectually challenging on a number of levels. It’s federal law but then it dips down and pulls up strands of divorce and criminal and probate and corporate and tax and partnership, and so I was able to use some of everything I learned at the Court of Appeals. For example, if someone is filing bankruptcy and they’re getting a divorce, there are divorce aspects. I like the fact that it’s federal but it dips down and pulls up state law, too, and it’s got a lot of procedural complexity because of the nature of the jurisdiction. So you can use it creatively, to look at what law should apply and “How do I structure [it] to kind of get the results I want?” Then the fact that the lawyers who practice it are really great lawyers, by and large, and it’s just a small community of people who all know each other. You can be on the same side one day and opposite the next day and still go out and have a beer.
Q: So you’ve got money problems. But you’ve also got people problems.
A: You’re exactly right. I tell the young lawyers that I talk to that I divide lawyers not into courtroom and noncourtroom, but into people lawyers and paper lawyers. There are lawyers who are high-volume people, like my father had been a high-volume people lawyer, but he didn’t have much paper involved. Then there are the high-volume paper lawyers, and those could be tax lawyers or corporate lawyers; even some litigators who don’t do that many trials are high-paper. The skill set for handling high-volume people versus high-volume paper is completely different. The thing that is so interesting to me about being a bankruptcy lawyer is we are high-volume people and high-volume paper. It’s a little bit schizophrenic sometimes.
The other thing is, this is not happy law. I remember I was getting ready for trial and working really hard with this client, and he looked at me, about midnight, and I was still a young baby lawyer, and he said, “Cynthia, you don’t do any happy law do you?” And I just kind of went, “Wahhh! I don’t do any happy law!”
Q: How do you deal with unhappy law?
A: When you’re dealing with a high volume of people who are unhappy, you have to be empathetic. I’m a big believer that you don’t beat them up. They’ve already done a much more effective job of beating themselves up than you ever could. But you can’t let them transfer all their problems to you. One of my friends who’s a lawyer gave me this analogy and I try to keep this image in my mind: Everybody has a monkey on their back. And many clients … want to put their monkey on your back. Well, you can help them feed their monkey, you can help them tame their monkey, you can help them get the monkey off, but it’s their monkey.
Q: You added to your star power by opening your own firm in 1995.
A: I had worked at several firms, they were all good firms. [I] liked the people, liked the work I was doing, but there were what I would say “structural issues” in the way firms were set up or organized that prevented me from reaching my goal of being a bankruptcy star. I decided in 1995—I’d been out about 10 years at that point—that I needed to go out on my own. I had some encouragement from some people who were mentoring me who were saying, “You don’t need to work in anyone else’s shadow.” And I just jumped off the cliff. My mental image was—I’m a big believer in mental images—Thelma and Louise. I was Thelma-and-Louise-ing off the cliff because at that time, I had no track record of bringing in business, and I just said I have to do this for my own well-being. So I went solo for a year. I had some people help me, and office-shared with a firm that said pay us rent when you can. I assumed that I’d have time to set up my practice leisurely but the money … the clients just started coming! I started getting referrals and was immediately busier than I knew what to do with. And then my [current] law partner, Steve Rebein, approached me … I had met him when I was clerking, and he’d gone off and been partner in a big firm. We decided to join forces. We opened August 1 of ‘96, basically with two lawyers and two paralegals. A bankruptcy boutique. That’s what we’ve done ever since.
Q: What are you most proud of?
A: You know, I represent so many people who have just hit rock bottom. And they think they’re losing everything: their homes, their businesses, their health, their marriages, their relationships with their children. Because when you go into debt … it’s so distressing and it impacts everything. … I mean, people commit suicide over it. I think what I’m most proud of is that I’m able to help them. I make them see it’s just about money, at the end of the day, and if you’re an honest person, then there’s a way we can use our bankruptcy process to help fix the problem—which is a money problem. And by fixing that, a lot of times that spills over in the rest of their life.