Photo by Laura Barisonzi. 

No lawyer wants to take a case all the way to trial only to realize a carefully refined courtroom strategy has to be discarded for something else. Especially when that something else is a complete unknown.

But the ability – make that agility – to change gears is crucial for a successful trial lawyer and can be one of the most important parts of the job, says Karen Dyer, who as the first – and at that time only – female partner when the Firm was founded in 1997 counts founder David Boies among her mentors.

“Trials are real time, fast-moving, and ever-changing,” she says.  “They require you to think hard, and to think on your feet.”  Sometimes literally on your feet. Dyer vividly recalls defending a major client in a summary judgment hearing in U.S. District Court in Manhattan that spanned 11 hours over a few days. She spent much of it standing while the judge peppered her and the other side’s attorney with questions.

“I remember on one of those days pulling more comfortable heels out of my purse, because I was unsure how much longer I’d have to stand.  As I explained to my team, preparation comes in many forms.”

That’s the (not so) glamorous life of top trial lawyers, a group whose female membership is growing but at a glacial pace. That’s true of the legal profession overall, where women make up nearly half of summer associates yet only 22 percent of partners at the nation’s 200 largest law firms, according to the most recent statistics from the American Bar Association.

To bridge that gap, Dyer says, firms should consider non-traditional paths to partnership, and take deliberate steps to help women develop clients and rise through the ranks of firm leadership.  This is particularly important because women are often the primary child caregivers at the most critical juncture of their careers.

It’s a dilemma Dyer encountered early in her career as an associate at Carlton Fields in Orlando, working with partner Anne Conway, who is now a retired Chief Judge of the Federal District Court for the Middle District of Florida. Dyer was on maternity leave after giving birth to her first child, apprehensive about leaving him at all, much less to return to work.

“Anne came and literally dragged me out of the house for a social event,” Dyer recalls. “She had little kids and knew how to balance family and being a successful lawyer. She made me get out of my comfort zone, yet feel like if I walked into her office and said, ‘I’ve got to go home, we’ve got an emergency with the babysitter,’ she wasn’t going to hold it against me.”

After clerking for federal judge G. Kendall Sharp, Dyer started her career in private practice representing the FDIC/RTC in connection with the savings and loan scandal of the late 1980s which was punctuated by the Michael Milken junk bond litigation. Dyer left Carlton Fields to form her own firm to work with the FDIC/RTC during the height of this litigation, then joined Duker Barrett – a Cravath Swaine & Moore spinoff – and joined Boies Schiller the year it was formed.

Nicholas Gravante, co-managing partner of Boies Schiller, serves on the firm’s executive committee with Dyer and has handled numerous trials alongside her, including their $664 million jury verdict in Marshall, Texas, in a whistleblower case against Trinity Industries.

“The term ‘trial lawyer’ is the most over- and inappropriately used term in our profession,” says Gravante. “Less than one percent of litigators are actually trial lawyers and most litigators who call themselves trial lawyers have never picked a jury, examined a witness or given an opening or closing statement. Most are pre-trial lawyers.

“There are only a handful of true corporate trial lawyers across the country and, unfortunately, most of them are men. But Karen Dyer is the real deal. She emerged as a top Boies Schiller trial lawyer nearly a decade ago and is now one of the top, true female trial lawyers in the country. Our most important clients attest to her talent on a daily basis as she already has four trials scheduled over the next year.”

Tenacious, self-effacing and remarkably connected, Dyer has worked alongside and learned from the best, and for decades has made her presence known in boardrooms and courtrooms throughout the country.

Lawdragon: That’s quite a trial schedule. Tell me about the cases and how this perfect storm came about?

Karen Dyer:  When it rains, it pours, but it beats waiting around for the phone to ring.  Nike has a trial upcoming in October in federal court in Orlando and brought me in as lead trial counsel over a year ago. My partners, David Boies and Bob Dwyer, asked me to help them try the well-publicized Greenberg v. Spitzer defamation case scheduled in New York this January.

Phil Iovieno – one of Boies Schiller’s preeminent antitrust lawyers – brought me in to co-try a major antitrust case with him for medical equipment company Angiodynamics in federal court in Albany this spring. And Nick Gravante and I will try a case in New York against Deloitte on behalf of Starr Companies, likely within the next 12 months.

LD: Sounds like a lot of traveling and coordinating during a difficult period. How are you finding it?

KD: Covid has definitely presented challenges, but I feel like I’ve lived on planes and navigated logistical complexity throughout my career. But the teams I’m working with are outstanding, my colleagues are great and we are all rowing in the same direction.

I probably average over 30 conference and Zoom calls per week, but like my colleagues, when I need to be somewhere I get there. One day people may be able to do trials from their living rooms, but that’s not for me. I’ll be in a war room with my team because trials are truly collaborative undertakings.

LD: How’s the firm doing? I know you’re in the middle of a restructuring.

KD: It’s progressing, but it’s not easy for any firm to restructure to the extent necessary to transition from one generation to the next. Nick Gravante and Natasha Harrison, our new managing partners, have certainly had their hands full and I admire them for all they are doing. They are making the difficult decisions that needed to be made.

LD: You’ve mentioned the issues facing women in the legal profession. What do you think are the most important today, and how can we address them?

KD: Some of them aren’t new, although women and their firms hopefully are becoming more flexible, creative and determined to resolve them. They include how to reconcile home life with a demanding work schedule, how firms can better assist women to become significant business developers and lead trial lawyers in major cases and how women can become firm leaders at the highest levels.

Flexibility in working remotely, recognition and acceptance of non-traditional work schedules and ensuring that attorneys who avail themselves of this aren’t penalized or delayed in their career development is key. It can be hard to measure on a purely quantitative basis; there has to be a mechanism to qualitatively measure the contribution.

LD: As far as remote working, do you think the widespread adoption of it during the coronavirus pandemic will make the practice more common going forward?

KD: I think it will have a dramatic long-term impact. It will allow people to telecommute for a portion of their work week, and courts will rely more heavily on telephonic and video hearings.  While certain things will still be done in person, it will provide more flexibility to attorneys about how and where to work. The flip side is, we will lose some of the positives resulting from personal interaction and collaboration.

LD: Do you have thoughts on the path you and other Am Law 100 female trial lawyers have paved – without the benefit of many female role models? What advice would you give women (and men) today who want the courtroom to be their home?

KD: Don’t be afraid to take risks. Don’t be afraid to be yourself and acknowledge to others that you have a family or interests outside the law and that you expect your colleagues to respect that. Men in the practice of law have no problem leaving a meeting early to go to their children’s recital or Little League game, etc., yet women – even if they’re the primary caregiver – feel the need to apologize. You’ll get more respect with fewer apologies.

LD: That’s a good point. Figuring out that balance in the workplace can be like walking a tightrope, especially in law firms. Where did you get the idea to become a lawyer yourself? Did you have relatives who were attorneys?

KD: I was the first one in my family to go to grad school.  We didn’t have any lawyers in the family, but I talked about wanting to be a lawyer when I was a child. And my dad worked with a number of lawyers as the president of a private holding company that owned Pepsi bottling franchises, and he and my mom always encouraged me.

LD: You have such a great understanding of business. Did that come from your dad?

KD: He was an accounting major by trade, though he worked as a firefighter before going back to school and completing his degree in his mid-30s. After finishing his degree, he started as comptroller at one of the businesses owned by the private holding company and ultimately became CEO of the holding company.

He and my mom – who never had the opportunity to go to college before having four kids, but has a sharp mind for business herself – always encouraged me to get a business or accounting degree and that’s what I did to ensure I’d have a marketable profession even if I didn’t go to law school.

LD: So you grew up in South Florida and got your degree in accounting from University of Florida, where you then enrolled in law school. When did you get the idea to become a trial lawyer?

KD: Originally, I had the idea that with an accounting degree, I might want to go into tax law. But I pretty quickly decided in favor of litigation. And litigation to me always meant trying cases.

LD: Did your clerkship and early training at Carlton Fields make it clear you were meant to be in court?

KD: I found myself attracted to the challenges presented by complicated cases and the exacting requirements of taking a matter to court. There were really good firms on the other sides of those matters. It was the type of high-level, complex commercial federal litigation that I liked seeing when I was a clerk, and I had hoped to be able to practice.

LD: You were one of the first lawyers to join Boies Schiller after David left Cravath, and the first female partner at the firm. Can you talk a bit about some of your favorite trials?

KD: Certainly the qui tam case against Trinity Industries, involving claims that it had installed faulty highway guardrails paid for by the federal government. Anytime billions are at stake and you win a $664 million judgment, it’s memorable. But the two jury trials it took to get there in Marshall, Texas were remarkable because we were such a small team up against an army of lawyers from what seemed like every major law firm in Texas. Although, as we suspected might happen, the judgment was reversed on appeal, the national media attention garnered by our trial victory resulted in intense federal and state regulatory scrutiny of the guardrail design at issue and our highways are now safer because of it.

I’m also proud of our multi-billion dollar trial victory in the Arizona Iced Tea war, where I worked on Long Island with a great team for many months. Because of my family’s experience in the beverage industry, I had a head start in that case and enjoyed handling the industry experts at trial. Again, that was a true team effort and my partner, Helen Maher, orchestrated one of the most organized trial efforts I’ve ever seen.

My trial work on the SICO cases on behalf of Starr Companies, headed by former AIG Chairman Hank Greenberg, also stands out. We successfully defended against a $5.3 billion claim by his former company, AIG.  It was a complex, hard fought trial and the judge was rigorous, but the jury got it—which doesn’t always happen.

LD: And tell me about the Dragon Naturally Speaking cases, which required you to employ both your bankruptcy and financial skills.

KD: For seven years, from 2000 to 2007, I handled a series of cases representing the majority owners of Dragon Naturally Speaking, the voice-recognition software that is the basis for the current generation of speech recognition software. The cases related to the fiasco that arose from the sale of Dragon for $600 million in stock to publicly-traded Lernout & Hauspie Speech Products, which went bankrupt immediately after the sale. As a result, I was in bankruptcy court for two years and had to separately pursue a number of commercial and investment banks and accounting firms in federal court in Boston.

Those were interesting cases for many reasons. Even though the cases were in Boston, most of the witnesses were in Belgium, where the company that had purchased Dragon was based, and I was living in Orlando. Let’s just say I earned a lot of frequent flyer miles.

Those cases were also interesting because it was just me and one associate handling the matter from Boies Schiller. I was 30-something years old when it started and still learning the ropes. I’m not sure that experience will ever be replicated because as my practice and the amounts at stake at my trials has grown, so have the size of the teams.

LD: In the Dragon matter you ended up achieving some great results for the clients, James and Janet Baker, who had developed the software and then sold it to Lernout & Hauspie Speech Products. Can you talk a little about that?

KD: When Lernout & Hauspie went into bankruptcy, the Bakers had nothing but stock. They had exchanged stock in their company for this Nasdaq public company’s stock. As a result, I felt like, “Great. We’re trying to get blood from a stone, because creditors come first.”  The case was further complicated by the fact that Lernout & Hauspie was a Belgian company, so in addition to the U.S. Bankruptcy, there was a parallel bankruptcy in Belgium (called a Concordat) and the debtors tried to play the two proceedings off of each other to see where they could get the most favorable result.

The argument I made to the U.S. bankruptcy judge was that, because the transaction with Dragon was actually a merger, my clients’ private company had actually merged into Lernout & Hauspie’s solvent U.S. subsidiary and, as equity holders of the solvent U.S. subsidiary, had priority over the majority of other creditors.

And we prevailed before the bankruptcy court, which prompted a settlement that gave my equity clients money even though not all the creditors in that bankruptcy got paid. But we had to agree to vacate the order because none of the bankruptcy litigators wanted our deal out there as precedent. And I don’t think the more experienced bankruptcy lawyers I was up against in that case ever thought that some young female lawyer from Florida was going to argue that strenuously for such an unusual result. They were like, “You don’t understand. This is not the way it’s done.” And I said, “Oh, no. I understand perfectly.”

LD: I think you secretly like rolling up your sleeves.

KD: Probably. Taking what you have in a case, not what you wish you had, and finding a way to make it work for your client, to fit those puzzle pieces together, is definitely one of my favorite parts of my practice. That’s why trials are so much fun. Evidence goes in a piece at a time and jurors often have no idea why they are being presented with certain bits and pieces while it is being presented. Putting it all together for a jury at the end of a trial and watching their facial expressions when they finally get it, when they finally see the entire puzzle, is very rewarding.

LD: Can you talk about the lessons you’ve learned from working on so many important trials over the years?

KD: The one thing I’ll emphasize over everything else is the importance of always maintaining your credibility before the court. That is crucial throughout your career, not just throughout a given trial. Also, maintaining flexibility as a case and trial unfold is crucial because you never know when you need to shift gears. Trials are like playing chess, in addition to knowing the record inside and out, you have to think several moves ahead.