Q&A with Of Counsel Rupita Chakraborty

By Katarina Marcial

Editor Katarina Marcial chatted with Of Counsel Rupita Chakraborty in the Firm’s New York office to learn about her career journey, what motivates her, and what advice she has for aspiring lawyers.

Monitor: Can you share a little about your background?

Rupita Chakraborty: I grew up in the suburbs of Boston. My family also lived in Kenya for a short time during my early childhood. After earning my undergraduate degree, I served as a Fulbright scholar in Indonesia, where I taught at a boarding school for about a year as an English Teaching Assistant. Upon my return, I worked on the Obama campaign in Nevada, and soon after that, applied to law school. While at NYU School of Law, I participated in the Federal Defender Clinic. I care deeply about public defense and prisoners’ rights, and my clinic experience was important in crystallizing the importance of those issues in my legal practice. To this day, I surprise myself with how much my thinking about client advocacy and storytelling is rooted in my clinical education.

After law school, I clerked in the Eastern District of New York. I then worked in Big Law and at a smaller defense firm in the city, focusing primarily on white-collar defense (dealing with both the DOJ and state and local regulators), large-scale investigations, and complex commercial matters. I also maintained a robust pro bono practice, at one point focusing particularly on Section 1983 prisoners’ rights issues.

Monitor: What inspired you to pursue a career in law? What interested you in securities litigation?

RC: I’ve always been acutely aware of how the law molds even the most rudimentary acts of daily life, a perspective deeply rooted in my upbringing as the daughter of immigrants. Obtaining identification, basic medical care, and ordinary social services—these are simple acts that are profoundly governed by our relationship with the state. Legal advocacy is a natural consequence of that awareness. And, as a litigator, I love learning about new parts of the world. Whether it’s technology, pharmaceuticals, or derivatives trading, I relish diving into the intricacies of a brand-new industry.

My interest in securities litigation was particularly sparked by my previous experience on a criminal case involving charges of RICO conspiracy and securities fraud. The case culminated in a nine-week trial in the Southern District of New York.'

Monitor: What brought you to Pomerantz?

RC: I was looking to elevate my career to the next level, and having spent significant time on the defense side, I was drawn to securities litigation and plaintiffs’ side work. Investing is a critical tool for everyone, so the prospect of defending shareholder rights held natural appeal. And the experience has been rewarding so far. Our current case against Philips is a perfect example. For over a decade, Philips’ CPAP and ventilator devices—used by vulnerable patients with serious respiratory conditions—contained sound abatement foam, which over time degraded into small particles, releasing toxins that could be ingested or inhaled by users. This ultimately led to a massive recall, impacting about 15 million devices, at the height of the COVID-19 pandemic, no less.

Philips is the kind of groundbreaking case that makes Pomerantz stand out—a matter that is at the forefront of shareholder rights, with a litigation strategy that is aggressive and cutting-edge. I find that philosophy of litigation to be particularly refreshing.

Monitor: What case has been most rewarding so far?

RC: That’s a real Sophie’s Choice! All my cases are rewarding at some level. I’ll say that pro bono work has always been a real source of joy for me. One particularly rewarding experience was representing a victim-witness in the Lawrence Ray RICO and sex trafficking prosecution in the Southern District of New York. The work involved preparing the client for testimony, document review, and briefing novel issues related to the federal psychotherapist privilege. Our client’s testimony was compelling, contributing to Mr. Ray’s conviction on racketeering and sex trafficking charges, among others. Our briefing also led to a precedent-setting opinion about the psychotherapist privilege that will hopefully encourage victims of sex crimes to seek mental healthcare freely and without fear or stigma.

Monitor: How has mentorship shaped your career? Which mentors have had the most influence on your professional development?

RC: Mentorship in the law is invaluable because a well-rounded practice requires a full throttle of skills—intellectual (writing, fact analysis, storytelling), emotional (listening, negotiating, managing), and organizational (time management, delegation). Mentors can guide you through the push and pull of those processes. And they can help you appreciate that the development process is organic—there will be ups and downs along the way. The mentors who helped me most led by example. They encouraged me to think creatively, listened to my ideas, and helped me identify my strengths. They embodied an openness that I now aspire to emulate. They also helped me see that there is an art to strategizing a position. Knowing when to be aggressive and when to pull back requires delicate balance and impeccable judgment, but ultimately, it’s a powerhouse skill.

I’ve had numerous mentors who have helped me throughout the years. My clinical professor in law school was the first to recognize my aptitude for cross-examination, and I am grateful to several law firm partners who gave me confidence in my writing and in my instincts vis-à-vis document analysis and issue spotting. They entrusted me with high-stakes opportunities early on, which helped me gain confidence and find joy in my work.

Monitor: What’s the best piece of advice you’ve received from a mentor?

RC: Sometimes, less is more. Refuting bad arguments with pages of briefing may come across as defensive, so it is often more effective to simply state that an argument lacks merit, provide a succinct explanation, and then move on to more substantive briefing. Another invaluable piece of advice I received is that the tighter your writing, the better. An exercise I used to do soon after law school was to review my work with fresh eyes and ask myself to articulate the added value of each sentence, and sometimes, each word. If a word or sentence didn’t add clear value to the argument, I would cut and revise. It’s a useful test of whether the brief is making the argument as succinctly as possible. I learned from a mentor that if you litigate every minor issue to the hilt, you risk distracting the court from the key two or three reasons why your client’s story should triumph.

Monitor: What is a piece of advice that you would offer to younger attorneys looking to make their mark in the legal field?

RC: Developing your writing, no matter where you are in your career, is always important. I still keep a running list of interesting words on my phone, and I add to it as I read novels or hear a compelling turn of phrase on a podcast. I also encourage my more junior colleagues to review redlines of their work after receiving edits from senior attorneys to understand the nuances of how the edits refine the language and elevate the argument. Also, as they advance in their careers, I encourage younger attorneys to transition from being task-oriented to argument-oriented. By connecting individual tasks to the key arguments needed to win, you not only improve your output on the task itself, but more importantly, can contribute meaningfully to the broader litigation strategy.