This year, Rob Kole assumed the role of Co-Managing Partner at Choate Hall & Stewart, where he has practiced for almost 30 years as a litigator handling high-stakes trial and appellate matters. Stepping into leadership as the firm celebrates its 125th anniversary, Kole now guides a Boston-based institution with deep roots in the city and a strong focus on its five core areas of practice: Private Equity, Finance and Restructuring, Patent and IP, Wealth Management, and high-stakes Litigation. We spoke with him about his career path, vision for Choate’s future, and the opportunities—and challenges—facing the legal profession today.
Personal & Career Path
What first inspired you to pursue a career in law, and how did you find your way into a focus on insurance and reinsurance matters?
Although I had no lawyers in my immediate or extended family, it seemed from an early age that it was almost assumed that I would become a lawyer, likely because of my propensity to argue almost any issue with anyone at any time – not always an attractive quality in a ten year-old. In grade school, I was assigned the role of prosecuting the big bad wolf in a mock trial and never looked back.
I found my way to insurance and reinsurance law accidentally. Very few people come out of law school thinking they are going to become insurance and reinsurance lawyers, and I was no exception. However, the first two cases I was assigned as a junior lawyer at Choate were insurance coverage cases, one a large, nationwide environmental pollution case, the other a smaller bankruptcy matter. I found the work interesting and really enjoyed the lawyers I had the privilege to work with on those matters, including John Nadas and Hugh Scott, who served as informal mentors and role models throughout my career. Looking back, it is remarkable how much the people you work with influence your career path, and I really hope I can pay that forward.
Looking back, what professional moments or accomplishments are you especially proud of from your career so far?
Not to be trite, but I am most proud that my partners asked me to serve as one of the Firm’s Managing Partners. Choate has been a Boston institution for more than 125 years. Titans of the industry have worked here, starting with our founding partners Charles Choate, Jr., John Hall, and Ralph Stewart, and continuing through the generations, including more recently Steve Cohen, Bob Gargill, Chief Justice Margaret Marshall, and another of my informal mentors, Bob Frank. We just finished a firm retreat, and I was struck by the quality of the people in the room, partners and business professionals alike. To be asked to help lead this group is humbling.
From a litigation perspective, I am particularly proud of some of the appellate results I helped to obtain on behalf of our clients. By way of example, I was the lead lawyer in: (a) two of the earliest opioid coverage cases in the United States, in the U.S. Court of Appeals for the Eleventh Circuit (Travelers Prop. Cas. Ins. Co. of Am. v. Anda, Inc., 658 Fed. Appx. 955 (11th Cir. 2016)) and the California Court of Appeals (Travelers Prop. Cas. Ins. Co. of Am. v. Actavis, Inc., 16 Cal. App. 5th 1026 (2017)); (b) the first public litigation in the United States over coverage for catastrophe bonds (Mariah Re Ltd. v. Am. Family Mut. Ins. Co., 607 Fed. Appx. 123 (2d Cir. 2015)); and (c) a case of first impression in the Connecticut Supreme Court regarding the meaning of “collapse” in a standard Connecticut homeowners policy (Karas v. Liberty Ins. Corp., 335 Conn. 62 (2019)). I am also proud of several successful large reinsurance arbitrations I have tried but those are, unfortunately, subject to confidentiality restrictions, as reinsurance arbitrations often are.
Leadership & Choate’s Future
Choate recently celebrated 125 years as a Boston-based firm. Looking ahead, what are your strategic priorities for the Boston office in both the near and long term?
We are in the early stages of a strategic plan, which has a number of components. There are at least four parts on which I plan to focus. One is balancing necessary and tactical growth with maintaining what differentiates us in the market: the low leverage and hands-on partner attention that have become our hallmarks. Two is developing firm wide initiatives aimed at modernizing our client service. Three is maintaining a continued focus on our firm-wide culture that inspires the highest energy and standards, relentless positivity, and a shared commitment to our clients and each other. Four is identifying and developing the next generation of leaders. If I am successful in doing those four things, Choate will be well-positioned for continued short and long-term success.
Choate has been a sponsor firm partner of the Boston Bar Association for 36 years and your attorneys have held several leadership positions within the BBA, most recently our White-Collar Crime, Bankruptcy, and Business Transactions Sections. How does this kind of engagement fit into the firm’s strategic goals and contribute to attorney development?
One of our principal strategic goals is greater involvement in the Boston community. This is especially important for some of our younger lawyers, particularly those who started in the COVID years working remotely and never developed ties to the greater community. We are encouraging those lawyers in particular to get more involved in the BBA.
But to be clear, BBA involvement benefits all of us, whether we are talking about further legal education, developing referral sources or participating in appropriate and necessary advocacy. I was reminded of these things when I attended the recent Spirit of the Bar event recognizing (among other deserving winners) our former colleague, Chief Justice Margaret Marshall. The event itself was great, and Chief Justice Marshall delivered a moving speech that brought the house down. But what I will remember most was re-connecting with colleagues and friends across the Boston legal community, including a large number of Choate alumni. It reminded me why BBA participation is so important.
What do you think sets Choate apart as a place where top legal talent wants to build their careers?
I like to think of Choate as offering the best of both worlds. We have the sophistication, industry knowledge and depth in our core areas to handle our clients’ most important, interesting and complicated matters, and to compete at the top of the market against the largest firms in the country. Yet, because of our size, and the fact that we have one office in Boston, we know each other well and can work closely with people we like and trust. Also, because of our low leverage model, all levels of talent get more, and better, opportunities to take on tactically important work earlier in their careers. So, for those looking for a Firm that offers top-of-the-market work opportunities with a strong culture of collaboration and accountability, Choate is a very attractive option. And it doesn’t hurt that our 2025 summer program was ranked #1 in the country.
As an aside, Boston is known as an insular legal market. Law students often go out of their way to identify their “connection to Boston” during interviews, fearing that absent such a connection they won’t be hired. When I interviewed at Choate for a summer associate job in 1994, it was the first time I had ever stepped foot in Boston, or Massachusetts for that matter. I was a public-school kid from Central New Jersey (and yes, despite the longstanding debate, there is a Central New Jersey) who went to college in Pennsylvania and law school in Virginia. Choate took a chance on me, for which I will forever be grateful.
How would you describe your leadership philosophy, and what impact do you hope it will have on the culture of the firm?
Although I am new to the Managing Partner job, I have always believed strongly in a handful of core principles that I believe translate to any leadership role. One, it is critical to lead by example. If you want people to work hard, you have to work hard. If you want people to put the Firm first, you have to put the Firm first. If you want to set a certain culture, you have to act consistent with that culture 100% of the time. Your actions have to match your words if they are to have credibility. Two, be honest and direct with people. I have always appreciated direct and candid feedback, even if I didn’t love the message. Three, it is okay to have a little fun. We have a hard job, and we work long hours. There is no reason we can’t take some time to enjoy it, and each other. For any firm to succeed long-term, there needs to be a glue other than money that holds it together and makes people want to join, and stay. People need to believe in what they are doing, and they need to enjoy the people they are doing it with. We have that culture at Choate, and I see one of my main jobs as helping to fortify that culture. I am lucky enough to follow great role models as Choate’s Managing Partner in my time at the Firm, from Bob Frank to John Nadas to Bill Gelnaw, to now Charles Cheever, all of whom exemplify these principles.
The Practice of Law Today
Boston is a unique legal market, with strength in life sciences, healthcare, and financial services. What opportunities does this environment create for your practice, and how has it shaped your own career?
Although the Firm’s insurance and reinsurance clients are located around the world, one of the largest is headquartered in Back Bay. It is an incredible organization with strong ties to the local community, and the people I have worked with there have helped shape my career.
More generally, the Boston market aligns perfectly with the Firm’s five core practices: Private Equity, Finance and Restructuring, Litigation, Patent and IP, and Wealth Management. While we practice nationwide, Boston provides an excellent base for each of these practices.
Client priorities and expectations have shifted dramatically over the past decade. How have you seen those changes play out, and how has Choate adapted?
Our clients have always had extremely high expectations and have demanded quality work, excellent service and partner-led teams, which we have always endeavored to provide – that has not changed. One difference I have noticed is a greater focus on accurate budgets and data security. Thanks to our excellent finance and IT teams, we have been able to meet those expectations.
Innovation and technology—from AI to data analytics—are transforming the profession. How do you see these developments shaping legal practice at Choate?
This is an issue we have spent a lot of time talking about in the context of our strategic planning exercise. A few themes have developed. First, we do not believe the common refrain that technology and AI are going to replace lawyers, particularly young lawyers. Clients hire us for our expertise and our judgment, and AI won’t change that. Second, some of the tasks that young lawyers will be asked to do may change. We therefore need to double down on our training and development programs to account for these changes. Third, to the extent technology can handle certain tasks, that will work to our benefit, as it will make it easier for us to get work that clients have traditionally thought could only be sent to a firm with 1,000 lawyers. Fourth, it is critical that we take advantage of any new developments in technology, to the extent they allow us to provide more efficient, and better, service to our clients. Fifth, it is important that we not only encourage young people to use technology, but that we allow them to lead. It is often the younger people who are best positioned to identify how best to take advantage of technological advancements.
You’ve built a career as a trial and appellate litigator. What advice would you give to younger attorneys who want to strengthen their courtroom skills?
I would give three pieces of advice. First, on matters you are working on, ask for opportunities to argue in court or handle witnesses at hearings and trials. Sometimes, the best way to get a chance is to ask for one. The worst thing that can happen is that someone says no but appreciates the initiative. Best case: you get opportunities. Second, take advantage of OJT time to witness trials and arguments, whether on matters you are working on or other cases in the office. And if your firm doesn’t recognize OJT time (Choate does), go on your own time. Third, look for pro bono cases that will have courtroom opportunities. Or, if your firm, like ours, has a relationship with a local prosecutor’s or public defender’s office, take advantage of that program. Choate has a partnership with the Suffolk County District Attorney’s Office, which allows associates to serve as a special ADA for six months. I did the program 25 years ago. I tried a number of cases (bench and jury) and argued in front of a judge basically every day. The experience was invaluable.
Beyond client work, what role do you see Choate playing in Boston’s civic and professional community?
We think it is critically important that Choate continue to play a significant role in Boston’s civic and professional community, as we have done for the last 125 years. We do so in a variety of ways. I can provide a few examples. First, we have a Community Impact Committee, which is specifically dedicated to deepening the Firm’s longstanding dedication to service and civic engagement. Earlier this year, through that committee, Choate was a Premier Scooper Schools Sponsor for the Dana Farber Jimmy Fund Scooper Bowl. Our sponsorship provided 500 Boston Public School students and teachers with free admission and transportation to the Scooper Bowl. Just as importantly, a substantial number of Choate employees volunteered for multi-hour shifts scooping ice cream. We are also partnering with the Massachusetts Coalition for the Homeless on December 2 to help build twin beds for 50 children across Massachusetts and Rhode Island who currently lack a safe and comfortable place to sleep. I will confess, as maybe the least handy person in the Commonwealth, I am mildly concerned about my bed building abilities. Second, Choate works with several local organizations in providing pro bono services, including the EdLaw Project, Lawyers Clearinghouse, Lawyers for Civil Rights the New England Innocence Project, PAIR, and the Center for Women and Enterprise. Third, Choate partners serve as board members for several local charitable organizations, including the Boys and Girls Clubs of Boston, with whom we have partnered for decades. These and other community activities are central to who we are as a Firm with a long and storied history in Boston.
Closing & Personal
What do you find most energizing about stepping into the Co-Managing Partner role?
I have the good fortune to step into the job as we begin a new strategic planning exercise that allows me to help set the direction of the Firm for at least the next decade, which is, of course, an exciting opportunity. But really, nothing is more energizing than working every day with our lawyers and business professionals. Their talent, generosity and positive attitude makes difficult things easier and easy things more enjoyable. And, I really enjoy working with my co-Managing Partner, Charles Cheever. Charles and I have known each other for 30 years – he was actually my writing TA at UVA Law in 1994. And although — or maybe because — we have very different personalities, backgrounds, and experiences, our skill sets complement each other well. More importantly, relying on and watching Charles perform the job at such a high level allows me to pick up some of the finer points more quickly.
And finally, on a lighter note—outside of work, what’s your favorite way to spend time around Boston?
When I first started at Choate, I lived in the North End, and then Charlestown. We moved to Andover more than 20 years ago, but still very much enjoy going into Boston. Although it is impossible to identify all of the things we like doing in Boston, I’ll name four:
- My wife and I at least twice a month head into Boston for lunch and a walk through the Common, the Public Garden and around the Charles. It really is a beautiful area.
- My kids, who are now 23 and 21, have always been theater fans. As the middle of three boys from New Jersey who liked and played sports, the theater world was admittedly a bit foreign to me. But we have been members of Broadway in Boston for more than a decade, which means dinner and a show at either the Opera House or the Colonial Emerson Theater five or six times a year. Our family loves it!
- My wife and I like comedy shows, and the Wilbur always gets good comedians. We see a handful of shows there, and in other Boston venues, every year.
- Since our kids were little, we have done a Christmas Scavenger Hunt in Boston, starting in Faneuil Hall, on Christmas Eve day. Even though the kids are now in college and medical school, respectively, we still do our Scavenger Hunt in the city every year. Never grow old until you have to!
