When the 1990s tech bubble burst, one of the major legal battlegrounds was over the alleged rigging of IPOs by the major banks underwriting them. The top IP lawyers in the country were consumed by the work, and any young associates lucky enough to be a part of it got a crash-course in complex, high-stakes work as the world was watching.

Meanwhile, in one corner at the white shoe powerhouse of Sullivan & Cromwell, a promising new associate who had just joined the case ducked into her office to do a quick Google: “What is an IPO?”

“I had a knack for the work and people knew I had promise, but I was incredibly fresh,” says Taleah Jennings. The child of academics, she had no exposure to lawyers before college, and had planned on going into social work until a course in Family Law flipped a switch in her.

Now a partner at Schulte Roth & Zabel known for her devastating cross-examinations and her complex commercial litigation work for private equity funds, commercial real estate firms and fiduciaries of large trusts, Jennings happily recounts her early days to law students and summer associates.

“I think it’s important for people to know,” she says, particularly first-generation law students. “We all start somewhere, and you have to embrace what you don’t know in order to learn more.”

Her down-to-earth attitude may contribute to her strength in the courtroom. Clients notice that she has an easy way of connecting to witnesses, whether they’re on her side or adverse, as well as with judges and juries. “I like to think of oral argument as a respectful debate over the law, as opposed to a fight,” she says. “Although I can have my claws out, too. I’m just strategic about when.”

In addition to her financial services work, Jennings has long had a robust pro bono practice that reflects her early interest in social services: She’s represented many domestic violence survivors in partnership with Sanctuary for Families, and has recently taken on cases related to birthing rights.

Lawdragon: What were your interests in childhood?

Taleah Jennings: I was interested in basically everything as a kid. I was one of those children who, if I went to a zoo, I wanted to work in a zoo. If I went to an ice cream store, I wanted to work in an ice cream store. My mother was an elementary school teacher and then administrator. My father's a college professor who teaches on urban affairs and social welfare, and they were both very involved in community efforts, so I had a natural drive towards social work. I really enjoy learning new things, so my social work studies exposed me to additional areas of study that resonated with me. It plays well into what I do now as a litigator, where every client and case brings new legal obstacles and challenges. With each new case, I become an expert in the facts and law applicable to the case, and it’s always changing.

LD: After your degree in Family Studies at the University of Maryland, how did you make the transition into law?

TJ: I received a Bachelor of Science in Family Studies. We studied families as a unit, we examined family economics, psychology, sociology – all aspects of family dynamics.

One of the required courses was Family Law. It was a senior level class, taught by a lawyer who structured it like a law school class. It really clicked with me. We had a family law case book, the same one I had later in law school, and I enjoyed reading the cases, issue spotting – the whole style of analyzing law. And my professor used the Socratic method, which I enjoyed. That way of studying and learning information worked for me, and I liked the substance of the cases we were studying, too. I made the decision to go to law school from that class. At the time, my goal was to pursue a career in Family Law.

LD: Tell us about law school at Rutgers. What was that experience like for you?

TJ: Law school was completely new to me. I had never, other than that one class, met a lawyer before. It was exciting because everything was new. I was like a sponge, absorbing all different areas of law and my interests just grew. I realized there's not just family law, there's not just criminal law. There's also this thing called corporate law that I'd never even heard of, and all these other areas. That was really the “aha” moment for me in law school. I had a narrow understanding walking in, but my eyes were wide open so I absorbed so much.  

LD: You were doing something right, because then you landed at Sullivan & Cromwell!

TJ: Honestly, I was so green, I didn’t even fully understand the prestige of that firm when I was in school. The on-campus interviewing process is very competitive, and I cast a wide net with my applications. People were very impressed that I was getting interviews with certain firms, and I started to understand the hierarchy amongst Wall Street law firms. When they offered me a summer associate position, I did my research and accepted what turned out to be an amazing start to my legal career. 

LD: How was the Big Law summer associate experience for you?

TJ: It was exciting. I like learning new things, but I couldn’t help sometimes feeling like I was playing catch-up. I remember my first assignment, a huge IPO litigation. All the major law firms were representing defendant banks. After I met with my partner mentor, he was telling me about how meaningful this case was and how exciting it would be for me to work with him on it. And then I went back to my office and Googled “IPO.”

LD: Oh wow!

TJ: I share these kinds of stories with law students and summer associates now, because it's important for people to know. Especially because there are so many more first-generation law students joining law firms these days. I tell them: Be comfortable with not knowing what you don't know. You'll learn. Don’t feel like everyone else knows what they're doing, either. The entire practice of law, for your entire career, is a learning process. You have to embrace what you don't know in order to learn more.

I just destroyed this guy on cross-examination. I’m going to not be humble for a moment: I killed it. I think even opposing counsel was sort of shocked and amazed. Litigators live for these moments.

LD: That’s such good advice. Was that IPO case the rigging of the IPOs in the 90s tech bubble?

TJ: Yep.

LD: That was a huge litigation.

TJ: Definitely. We represented Goldman Sachs, and we were liaison counsel for all of the defendants, so we had a huge role. We were in the middle of everything. My mentor was Vince DiBlasi, and he led that entire case. He was a great mentor. He took me under his wing and so I attended high-level meetings and got exposed to major players from other law firms, and witnessed many styles of lawyering. I became the point person at Sullivan & Cromwell for most communications amongst the defense team. I spent four and a half years there and that case was primarily what I worked on. It was great training ground.

LD: Do you keep in touch with Vince still?

TJ: I did. Unfortunately, he passed away a few years ago. I remember there was one day, shortly after I joined Schulte, that my partner mentor at Schulte, Bob Abrahams, called me up to a conference room where he was meeting with Vince. The two of them had a case against each other. Bob called me to let me know Vince was there and invited me up to say hello. When I arrived in the conference room, Vince said, “It's great to see you. Are you happy here? Or can I bring you back to Sullivan & Cromwell?” We all shared a nice laugh, and I love having that memory of two people who have greatly influenced my career in the same room at the same time. And when I made partner at Schulte, Vince called and congratulated me. We kept in touch.

LD: I love that. How did you choose Schulte after Sullivan? You must have had lots of options.

TJ: I was at a point in my life where I wanted a change. Don’t get me wrong, I was having a great experience, working with great people, but I was starting to ask myself what I wanted out of it. Did I want to stay at Sullivan?  Did I want to continue working at a large firm? I even considered whether I wanted to leave the legal field altogether. I had a close friend who worked at Schulte, and over the years, I had gotten to know the firm and its people through her, going to events and such.

I really liked the vibe and culture at Schulte. I liked how people interacted with each other. From what I could tell, people had the same level of respect and admiration for each other whether they were a secretary, legal assistant, partner, or associate – the culture of a true firm community was very attractive to me. 

Schulte also was one of the front runners – if not the lead – in the hedge fund and private equity space, an emerging area of practice in law firms. I realized I would have many opportunities to litigate challenging cases in that space for a premier law firm.

LD: Maybe you’d have a chance at more of a work-life balance at Schulte, too?

TJ: I thought that at first, since it’s a smaller shop. But you know, the opposite was true! But I didn’t mind. I actually loved it. Because I was observing less and doing more. I wasn't just preparing someone else for a deposition that they were going to take, or researching for drafts that someone else was going to write. I was, almost immediately, that person. I was lawyering.

I started working with Bob Abrahams immediately upon joining Schulte. And although it was never formalized, he quickly became my mentor. He had the mentality of: “I've been doing this a long time. Back in my day, people just sent you to court and you learned on your feet. So that's the approach I'm going to take with you once you show me you can handle it.”

So I was arguing motions, taking depositions, strategizing, finding witnesses to support our claims. I really felt like a lawyer. Looking back, I think Sullivan & Cromwell gave me great training, and Schulte gave me great opportunities to put that training into practice. And that takes all your time, because you're on the front line and you want everything to be perfect. Staying up till the wee hours of the night to prepare for a deposition that I'm actually going to do, just has a different feel to it. I started really enjoying being a lawyer, working on behalf of my clients. I felt very invested.

LD: How long until you made partner there?

TJ: About five years.

LD: How did it feel once you found out you got it?

TJ: Great, obviously. I remember I was in the middle of trial and I had cross-examined a senior executive from a London bank. It was the first major cross-examination I had taking in a high-stakes commercial litigation – there was approximately $100M on the line. A few partners and our clients were in the room that day because it was an important witness. I don't know who was more nervous: me, or the partners who let me handle this cross-examination – but it worked out for all of us in the end. I just destroyed this guy on cross-examination. I’m going to not be humble for a moment: I killed it. I think even opposing counsel was sort of shocked and amazed. Litigators live for these moments.

There are also cases in which epidurals are withheld because medical service providers want to push a “natural” birth. My experience working with domestic violence survivors has led me to these sorts of cases. They are about women's rights to have autonomy over their bodies.

Back in the office later that night, after word had spread about that trial day, one of the co-chairs of the litigation department came into my office and said to me, “Cross-examinations are one of the hardest things for litigators to do. Today was huge. I'm so proud of you.” Shortly after, the lead partner in my case came in and said to me, “All the right people were in that room today. You were amazing. We're going to put you up for partner this year and you are going to have the support of the entire department. Have an amazing weekend and relax.” So I did!

LD: What was the first trial that you fully led yourself?

TJ: I had a pro bono matter for Sanctuary for Families, in a specialized part of the New York Supreme Court called the Integrated Domestic Violence Part. It hears cases that involve both the Family Court and the Criminal Court.  We represented a survivor of domestic violence, who had been severely abused over the course of her marriage, even during her pregnancy. Some of the evidence I got into the record included a picture of her living room wall with her pregnant belly imprinted in it because her husband had thrown her into the wall while she was five months pregnant, and a samurai sword that he used to chop down a door that she was hiding behind while holding their newborn baby. It was really, really intense. The defendant (her husband) actually threatened to kill her while she was testifying on the stand and was arrested during trial.

LD: Wow.

TJ: I was working with this client from the very beginning in the case. We had a lot in common and we quickly developed a trusting relationship. We started with the understanding that the Legal Services Director of Sanctuary for Families would do the cross-examination, the closing, etc. But as the case went on, the client asked me to take on more and more. I did a mock cross-examination with her during trial prep, and she said, “I didn't know you could be so scary, because you're so nice.” When it came time to cross-examine the abuser, our team decided that I should do it.

I ended up examining every single witness, including a responding police officer and a number of eyewitnesses. I was so nervous, but Dorchen Leidholdt, Sanctuary’s Legal Services Director, assured me at the end of the trial.  She told me that, despite my nerves, she could tell I was in my element and told me I was a trial lawyer in her eyes. That was very meaningful to me, given Dorchen’s stature in the legal field and her expertise in client advocacy.

LD: Is there another case that stands out as particularly memorable?

TJ: Every case brings new challenges. One that really stands out is a case that went to trial in 2013. I had just become partner and it was a jury trial set to last five months. The dispute was a highly sophisticated, commercial dispute and our trial team had to keep the attention of the jury – most of whom did not have financial or commercial backgrounds – for five months. It required strategy, creativity and a lot of hard work behind the scenes.

This was my first time having a speaking role in front of a jury. At the end of the trial, one of my adversaries complimented me on my cross-examinations. She said, “You have a really great style, you know how to mix it up. Sometimes you're very friendly. You can get people to smile and laugh with you. And then you surprise a witness with a really sharp, confrontational thing. It’s really effective.” She was an experienced trial lawyer, and I appreciated her words – I love when women, even when we're adversaries, can support each other.

Another reason this case was memorable is that it ended in a huge victory for our client.

LD: Are there any other pro bono family law cases on your plate these days?

TJ: I always have a family law matter on my plate, but now I play more of a supervisory role so that younger attorneys can take the lead. I’m also starting to work in a new pro bono area, birthing rights. I currently represent a woman who was the victim of birthing violence. As it is an open case right now, I don’t want to get into too many details, but what I can say is that her rights to choose (and reject) certain treatments, tests and procedures were completely disregarded. Both her and her newborn son suffered immensely as a result.

LD: What an important case to take on right now, with reproductive rights being stripped back on a wide scale.

TJ: Absolutely. These birthing rights cases are a major area right now. There's a lot of cases involving drug screening that result in false positive indications for illicit drugs. This can result in criminal charges, involvement by child protective services and other severe consequences. There are also cases in which epidurals are withheld because medical service providers want to push a “natural” birth. My experience working with domestic violence survivors has led me to these sorts of cases. They are about women's rights to have autonomy over their bodies.  The difference is that, in these cases, the abusers are not intimate partners, they are hospitals, doctors and other medical service providers. Like women who have trusted a partner, the women in these cases trust a medical system that abuses their power.

LD: What advice do you have for young people who are looking to have a career like yours?

TJ: Find an area of law that you like and work hard. Opportunities will present themselves to you. And some of those opportunities will be unexpected. You cannot get locked into: “This is what I want my career to look in 20 years and this is how I am going to get there.” The way you may get to your final spot, or just the next spot on your path, could be very different than the way someone else got there. Be open to considering different directions and following your own path. Finally, take your work seriously, but know when to put it to the side. Everyone needs balance and you are a better lawyer when you have that.