Overcoming the Odds: Why Policyholders Turn to Natasha Romagnoli for Their Most Contentious Fights

Whether you are a Fortune 500 company or a sole practitioner, there may come a time when things don’t go as planned. Where life delivers the unthinkable and we are left asking ourselves, “What do I do now? How do I fix this?” That is why both Fortune 500 companies and individuals alike purchase insurance – to protect themselves from these types of calamities. But as we all know, getting your insurer to pay is often no easy feat. That is when policyholders look to Natasha Romagnoli – when it comes to “bet the company” litigation over insurance proceeds.

Romagnoli, who has 25 years of experience in commercial litigation, is a partner in Blank Rome’s Insurance Recovery Group, one of the few practice groups in the country that exclusively represents policyholders in sophisticated insurance matters. Romagnoli’s insurance litigation and advisory practice runs the gamut from commercial general liability to employment liability, directors and officers liability to professional liability, property and business interruption to cyber, and more. She regularly steps in at the eleventh hour to help clients navigate everything from sex abuse scandals to mass shootings, to the murder of a college freshman and racially biased assaults on campus, and the attendant public relations crises and internal investigations that often follow. This is tough stuff, but Romagnoli is passionate about the fight.

Her clients describe her as “brilliant,” “sharp,” “fearless” and a “highly effective advocate.” The resounding sentiment though is how no-nonsense she is and how good she is on her feet. The past five years have seen Romagnoli ranked on countless industry lists, including Chambers, which ranks the best insurance coverage lawyers in the market. There aren’t many women on the list, but Romagnoli is one of them, and in some instances she is the only woman included on lists ranking policyholder lawyers. She is also a member of the esteemed Lawdragon 500 Leading Litigators in America. 

When we sat down to interview Romagnoli, she was in her New York office, still running on adrenaline, having only recently argued a case that has the potential to clarify New York law on bad faith and deceptive trade practices claims against insurers. There was a suitcase on her floor, and a box of binders had just been delivered to her office for several motions still to be argued in another case that month. One of her four teenage daughters had just stopped by to have a quick lunch with Romagnoli across from her at her desk. In a few hours she was catching a last-minute flight to lead mediations on a sex abuse case that had had intensified, for which she had been retained only three weeks prior.

That is Romagnoli in action – dedicated and devoted to prevailing for her clients in their most challenging cases, every moment of the day.

Lawdragon: How did you first decide you wanted to be a lawyer?

NR: I grew up in a small town in Central Connecticut. My father owned a metal stamping factory but even in the best of times we only scraped by. Then, when I was in law school, we lost everything. So I always felt like I was an underdog, and I knew that hard work would not be enough.

I had figured that out pretty quickly when I went off to Smith College and immediately joined the debate team. We traveled around the East Coast competing against the most prestigious schools that had debate teams that were decades old and had formal training programs lead by coaches. Anytime I made it to a final round against one of these schools in front of dozens if not hundreds of other debaters, and had to respond to arguments on the fly, I realized that prestige and pedigree only went so far.

Success in advocacy comes from being able to break down complex issues to get to the heart of what the decision makers need to care about. That often means tapping into someone’s sense of what is fair and then pivoting and adjusting depending on what is resonating with your audience. It came naturally to me, and I loved it. I knew in those early years that legal advocacy was what I wanted to do for the rest of my life.

LD: What were you like as a young lawyer?

NR: That sense of being the underdog persisted. I always felt very self-conscious about where I came from in a world where, at least in the beginning of a career, pedigree can matter so much. I didn’t want anyone to doubt that I was capable and so I worked as hard as I could, and then figured out ways to work even harder. The hard work wasn’t just about the hours at the office that I spent preparing. It also was about working smarter and faster – to always be the most prepared, to be several steps ahead of opposing counsel, and to spend time really questioning why things were done the way they were and figuring out whether there was a better way to do it. I also had to be tough and resilient as a young female attorney contending with far more experienced opposing lawyers in high-stakes commercial litigation matters in New York City. I remember during one annual review session being called both a “workhorse” and a “pit bull.”

LD: What an interesting combination. How did that view of you affect how you viewed yourself as a litigator?

I felt like my hard work and dedication began paying off early on and continued. I took my first witnesses at trial when I was a second-year associate. I had three trials in the next two years. And from there, I became the go-to associate for dropping into cases to take depositions or do arguments. What set me apart was my ability to digest immense amounts of information quickly and to strategize and outperform opponents who were far more familiar with the case file.

Success in advocacy comes from being able to break down complex issues to get to the heart of what the decision makers need to care about.

LD: When did you first starting practicing in insurance recovery?

NR: I was a complex commercial litigator for many years. I was already a partner at Kasowitz Benson Torres & Friedman working on a wide variety of litigation matters when I was introduced to Robin Cohen, who at the time was the head of the insurance recovery group at Kasowitz. She had a client who was embroiled in a real estate dispute, not involving insurance at all, and whose attorney in that case had just passed away. It turned out the attorney had not conducted any discovery, and the case was set to go to trial in three weeks. The judge refused to postpone it. I remember getting the call from Robin asking me to do what I had become used to at that point – coming in at the last minute on cases and taking depositions. It was intense, but after a demanding stretch of long nights, the case settled a week before trial with a home-run outcome for our client, who did not have to pay a dollar and instead received almost a full recovery on its counterclaim.

After that, I joined Robin’s insurance practice group. At the same time, Linda Kornfeld joined the group, bringing with her the Penn State Sandusky case. That was the very first insurance coverage case I ever worked on. Sandusky was an assistant coach at Penn State University who was arrested in 2011 and charged with 52 counts of sexual abuse of young boys over several decades. It was a turning point moment both for me personally to work on that as an attorney but also for the insurance industry in terms of how they started thinking differently about coverage for sex abuse claims.

Incredibly, even though Linda and I both left Kasowitz several years later to go to separate firms, she and I reunited when I joined Blank Rome in 2019 right as the last dispute with an insurer in the Penn State case was finally going to arbitration, so I got to finish what I started with her many years earlier.

LD: That is a pretty infamous case to cut your teeth on as an insurance coverage lawyer. There has always been such polarization over whether Penn State, and in particular Joe Paterno, covered up the abuse for all those years.

NR: It was a constant uphill battle to disabuse people of this reductionist narrative that this was an open and shut case about a university that cared more about its football program than about protecting young children. The most emotional part for me was when I stood up to start the closing argument in what was the last proceeding of a coverage case that had been litigated for almost a decade. By then, I had visited the campus dozens of times.

For years, I had a routine of going for an early morning walk all over campus, during which I would constantly refine how to explain who this place was to a jury (or an arbitration panel), to get past the preconceived notions so many people held. So fast forward years later, and in that instant before I said the first words of my closing, I saw flash before me what felt like all of those walks on campus, the conversations with people who had worked there, and all the in-depth strategy discussions with Linda – and I felt such a sense of responsibility to tell the story of what had happened.

And, even though it was the end of that case, it was the beginning of my time at Blank Rome, and nothing prepared me for how impressed I was with Linda and our partner Dave Thomas, who worked so closely with Linda on the case, and the rest of the practice group that I was quickly getting to know. I felt like I had just joined a brain trust with respect to insurance coverage law and actually felt quite intimidated with the amassed decades of experience housed in the Blank Rome insurance coverage group! It was just a really overwhelming intersection to have a case that had meant so much to me ending just as I was embarking on a new stage in my career at Blank Rome.

LD: What did you say in the closing?

NR: Unfortunately, it was a confidential arbitration so I cannot discuss any of it.

LD: What was it about insurance coverage that appeals to you even more than doing general commercial litigation?

NR: What I didn't appreciate before I started doing the coverage work was how intellectually challenging the coverage issues are in most cases coupled with having to constantly learn about the client’s business or operations and the internal and external pressures they have to contend with. But what I find most invigorating is that in almost every single case the odds seem stacked against the policyholder, either because it is smaller than the insurance company or because it is outnumbered.

I was just in Delaware on a case where I sat at counsel table with Dave, with whom I have continued to work on my largest sex abuse cases, and I turned around to look behind me just before starting on four hours of argument on roughly half a dozen motions. There was my client and the couple other members of the Blank Rome team, not even filling one row of benches. And, on the other side to my right, the two counsel tables couldn’t even fit all of the attorneys for the insurance companies who spilled over to fill the entire side of their courtroom. There could not have been a more striking visual at that moment of what a dogfight it often is between a policyholder and the insurance companies.

I didn’t want anyone to doubt that I was capable and so I worked as hard as I could, and then figured out ways to work even harder.

LD: It’s that feeling you had from when you were younger of being the underdog?

NR: Absolutely. There's something special about an insurance policy, even though at the end of the day it’s just a contract. For the most part, people only expect to call on those policies when they are in crisis and need immediate support and guidance from their insurer and funding to pay for defense costs, settlements, and potentially judgments in the underlying actions. There was something that spoke to me about how fundamentally unfair it is where you have a contract that is designed to protect you when you are at your most vulnerable – when you're in dire straits – and so often you have insurers who deliberately avoid that obligation. That's a horrible situation and fundamentally unfair.

You see the harms most pronounced when you have smaller policyholders who are not used to litigation. Maybe they have never even looked at their insurance policy before because they haven't had a crisis.

But without fail, it doesn't matter the size of the institution or the company or how much money they have, they are always dealing with an event that's not planned for in terms of being sued or having demands made against them. Then you have the insurers who are supposed to be arm-in-arm with them, who instead often open up another front of litigation that my clients have to then fight.

LD: How often do you find yourself suing insurers for bad faith?

NR: I will not include that claim just for the sake of including it or to try to gain some tactical advantage. There has to be real consideration given before pursuing a bad faith claim about whether the policyholder’s claims just amount to breach of contract. Otherwise, you risk your credibility with the court. That being said, I think the concept of bad faith is fascinating as it plays out in the insurance coverage context.

Since I came to insurance recovery after more than a decade of practicing as a complex commercial litigator, I look at what gets described in shorthand as a claim for “bad faith” by insurers as what it really is: a breach of the implied duty of good faith and fair dealing. That refocusing to think about what an implied duty claim means doctrinally, initially divorced from the type of contract out of which it arises, helps in so many aspects of pursuing that claim against insurers. Implied duty claims are always about frustration of purpose and depriving the other party of the benefit of their bargain. That’s a really straightforward concept, but the slight reframing of arguing how that concept has been applied generally across all different types of contract cases, which is completely appropriate considering that an insurance policy is just another type of contract, makes a huge difference in getting away from talking about “bad faith” as if it is some cheap litigation tactic by policyholders merely to gain some leverage over insurers.

I am really excited about the cases I’ve been involved in recently developing and advocating interpretations of implied duty claims in multiple jurisdictions. Drawing on more universal contract or tort principles to assert implied duty claims rather than limiting myself to traditional applications of bad faith law, such as in the duty to settle context, has so far benefitted my clients. And it’s confirmation for me that my approach to insurance law from a classic contract or business tort perspective, borne of years of doing general litigation rather than being steeped in insurance coverage litigation from the time I was a junior associate, is what works best for me as an advocate for my clients.

LD: How would you describe your style as a litigator?

NR: I do not shy away from challenging the status quo. Thinking creatively and being willing to confront “the way things have always been done” has led to a lot of success for my clients and advances in the development of the law. I’m probably a little bit less formal in my presentations than a lot of attorneys. I'm happiest during an oral argument when I’m opposing a motion or when it's a hot bench. I always work really hard before oral argument to distill down the cases and the argument to the points that are most intuitive and resonate in a sense of what is fair.

I have colleagues who tease me good-naturedly about my aversion to using PowerPoint slide decks to click through during argument. I’m much happier coming into court with a couple of huge, old-fashioned boards that I can put up on a tripod and walk over to during argument to breakdown for the court what is really at stake in the case, both legally and practically, and what the ramifications are for adopting the insurers’ position over my client’s. We had a case a few months ago where I kept telling the team to print the board bigger and bigger before I had actually seen it, and had asked for an 8 foot by 10 foot board in my exuberance as I got more and more excited about our chances of winning. Thankfully, someone pointed out I would have needed a ladder to stand in front of such a big board and talked me down to a normal size board.

Thinking creatively and being willing to confront “the way things have always been done” has led to a lot of success for my clients and advances in the development of the law.

LD: That sounds like the type of exuberance that led one of your clients to describe you as a “fiery advocate.” Do you think that’s an accurate description?

NR: I’d agree with the characterization of me as “fiery” insofar as it means that I’m passionate about my clients’ needs and interests. In terms of how I comport myself when I litigate, however, I always endeavor to be the calmest person in the room, whether it’s a conference room or a courtroom. But I also endeavor to be the most prepared and the most dedicated, which leads to me being relentless in how I represent my clients.

The preparation isn’t just about reading all the cases or knowing the record backwards and forwards. It’s about really getting to know my clients and their operations so that I am as invested as they are in the outcome of the case. I don’t ever lapse into thinking that this is just a job that I’m doing or this is just another case to get through. Many of my clients I get to know on a personal level, at least with respect to how the crisis of not having their insurers pay is affecting them, how it is making their own jobs much more difficult, and in some extreme situations, how it is threatening the very existence of the institutions or companies they love so much. So when I show up to advocate for them, whatever the stage of the case or whomever the audience is, I won’t stop until I’ve exhausted everything I can do to help them so that I can look them in the eye and say I’ve done my best.

LD: Natasha, tell us about your mix of practice within the insurance space.

NR: Obviously, a large part of my practice involves representing universities, secondary schools and non-profits in sex abuse coverage cases. Because of the reviver statutes that have been passed across the country, a lot of the cases I have had in the past few years deal with instances of abuse that occurred 70 or 80 years ago. But at this point, any institution that deals with children is susceptible to these types of lawsuits, and I see that in more recent cases where I represent corporate policyholders who are facing similar resistance from their insurers to cover these claims.

The work on the sex abuse cases can be emotionally draining at times, although not as much for me as for my clients. Thankfully, through my work with universities and colleges, I also deal with a lot of coverage disputes involving Title IX and race discrimination cases. Those cases are not so dissimilar to the sex abuse cases because most times, the school does not want the coverage fight to become public, which only serves to keep open what is usually a very sensitive chapter of their school's history behind them. When coverage litigation ensues, especially after the underlying cases are settled, it doesn’t let anyone move forward, including often times the victims. So as much as I love the fight in the courtroom with the insurers, in a lot of instances, depending on the policyholder and their unique circumstances, it’s about securing coverage as quickly as possible.

Some of my coverage cases do not involve liability insurance at all, such as property insurance and business interruption, which are an entirely different world and complex in different ways.

LD: How is Blank Rome for you as a platform for your practice?

NR: Blank Rome has a lot to offer that no other practice group that does policyholder-side work in the country can offer. When I first started doing coverage at my previous firm, I kept hearing about many of the attorneys at Blank Rome, and in particular hearing stories of what phenomenal trial lawyers they were. To get to work with people who had such a depth of coverage experience and were bona fide trial lawyers was a huge consideration for me. Blank Rome is also the premier practice in the country for sex abuse cases as a result of the tireless efforts of our practice group leader, Jim Murray, and the team he has built over many decades of practice, and because that part of my practice was really taking off at the time, there was a synergy with Blank Rome at the time that I could not have found anywhere else.

LD: You have built this thriving practice that requires you to work long hours and weekends, to travel and be away for extended periods of time, and yet you have four teenage daughters. How did you manage that and what advice do you have for young attorneys who are concerned about work-life balance?

NR: I find the phrase “work-life balance” to be counterintuitive. It implies that our work is separate from our lives. My work is a huge part of my life, and I am lucky that I love my work and my clients. My daughters have known from a young age that as much as I love being their mother, I also love being a lawyer. Too often people – especially women – seem to feel the need to apologize for being dedicated their jobs, and at times, putting their jobs first. So my advice for young attorneys is to try to find work that you truly feel passionate about, because there’s nothing wrong with your job, which inevitably takes up a huge chunk of your life, being a source of real meaning and enjoyment.