The interns participated in periodic “Lunch and Learn” sessions, featuring judges, lawyers and other professionals. The programs provided opportunities to learn, network, and hear firsthand accounts about public service. 

The following pieces were authored by Spencer Beran, Boston University, and Giovanny Esguerra, Binghamton University.

Kermitt Brooks and Russell Squire, moderated by Justice Jeffrey Zellan

By Spencer Beran, Boston University

On July 22, 2026, a recent Lunch & Learn for the interns of the New York Supreme Court brought together attorneys Kermitt Brooks and Russell Squire for a discussion drawing on their extensive experience in the insurance industry, and moderated by Justice Jeffrey Zellan. The speakers offered perspectives from two distinct sides of the field: Mr. Brooks, as a senior in-house legal executive, whose career has spanned private industry and government regulation and Mr. Squire, as an attorney representing corporate policyholders in insurance coverage matters.

Kermitt Brooks, who received his law degree from the University of Michigan Law School is the Chief Legal Officer of Guardian Life, where he oversees the company’s legal, compliance, regulatory, corporate governance, and government affairs functions. His career of more than three decades has placed him at the intersection of financial services, insurance regulation, corporate governance, and capital markets.

Before joining Guardian Life in 2020, Mr. Brooks spent approximately a decade at Equitable, formerly AXA Equitable, ultimately serving as General Counsel. During his tenure, he held senior legal leadership positions and played a significant role in Equitable Holdings’ approximately $3 billion initial public offering in 2018. Earlier in his career, Mr. Brooks served as First Deputy Superintendent of the New York Department of Insurance, now part of the New York Department of Financial Services, and briefly served as Acting Superintendent in 2009. His experience also includes helping lead the approximately $150 billion restructuring of AIG during the financial crisis. 

Russell Squire is an attorney in Reed Smith LLP’s Insurance Recovery Group in New York, where he represents corporate policyholders seeking coverage and recovery under their insurance policies. His practice encompasses a broad range of first- and third-party insurance matters, including commercial general liability, directors and officers (D&O), property, fidelity bond, representation and warranty, aviation, and cyber insurance. Over the course of his practice, Mr. Squire has helped obtain hundreds of millions of dollars in insurance recoveries for clients.

Before joining Reed Smith in 2022, Mr. Squire spent more than eight years as an associate at Covington & Burling. He earned his law degree from Georgetown University Law Center and gained experience representing clients as a student attorney with DC Law Students in Court while in law school. Beyond his legal practice, Mr. Squire has also been active in New York City civic affairs, including serving as Chair of Manhattan Community Board 8.

Together, Mr. Brooks and Mr. Squire brought complementary perspectives to a discussion of the legal and business issues surrounding insurance. Mr. Squire’s work on behalf of corporate policyholders provided the perspective of outside counsel advocating for companies seeking to maximize coverage under their policies, while Mr. Brooks brought the perspective of a chief legal officer responsible for navigating the legal, regulatory, governance, and business considerations facing a major insurer.

Their respective career paths also illustrated the range of roles attorneys can occupy within the insurance and financial-services industries. Mr. Squire’s career has centered on private practice and representing policyholders in complex coverage matters. Mr. Brooks, meanwhile, has worked across government regulation and senior in-house leadership, including during periods of significant change in the financial sector.

The Lunch & Learn gave the interns an opportunity to hear from attorneys whose careers approach insurance law from different vantage points. Their backgrounds demonstrated how insurance law intersects not only with traditional legal practice, but also with corporate strategy, financial regulation, risk management, governance, and major transactions. The conversation provided a useful look at the breadth of opportunities available to lawyers working in and around the insurance industry and the different perspectives that outside counsel and senior in-house attorneys bring to many of the same legal and business challenges.

Leonard Cascone and Olympia Rubino 

By Giovanny Esguerra, Binghamton University

When it comes to defending clients in the court system, it is hard to do better than Leonard Cascone and Olympia Rubino, Partner and Co-Managing Partner of the Cascone and Kluepfel defense firm located in Farmingdale, New York.

Recently, the New York Supreme Court’s summer interns got the rare opportunity to learn about trial and pre-trial experience firsthand from these highly skilled attorneys. In their lecture on July 24, 2026, both attorneys highlighted the importance of integrity, hard work, and not only winning your cases but getting an ideal result for your client. Both Mr. Cascone and Ms. Rubino must manage a high number of cases a year, but still, they try their absolute hardest to show care for their cases by visiting sights of accidents to find any way they can challenge previous depositions. It is simple things like that which can be easily overlooked, but taking the time and having the dedication to do that helps you know more about the case you have and, in turn, hopefully gives you an advantage in a trial setting. It is, also, that type of thinking that has led Mr. Cascone and Ms. Rubino to achieving winning verdicts – such as a potential $6.6 million verdict that was reduced all the way to zero.

Mr. Cascone made clear to the audience the nobility that comes with pursuing and working a career in law. He stays true to his values, no matter the situation he is in, including times where he had no choice but to turn down clients who were not willing to listen or previous work settings where he had no choice but to separate himself from other attorneys. He noted that maintaining your integrity and a proper image of yourself provides a unique advantage in the courtroom and in life as a whole. All participants in a trial – the Judge, plaintiff’s attorney, your client, and the jury each recognize your integrity and the genuineness behind that, creating an environment where easy communication, understanding and respect is just about guaranteed. Approaching life itself in a way that keeps you true to yourself also leads to much more fulfilling experiences in and outside the courtroom.

Ms. Rubino and Mr. Cascone continue to use their experience and knowledge to educate many audiences on trial advocacy. From their lecture, the New York Supreme Court’s summer interns were all given lifelong advice that would make anyone not only better attorneys, but better advocates and better people overall.