Tom Sabatino’s journey from a working-class upbringing in Norwich, Conn., to becoming a respected corporate general counsel is a testament to his curiosity, adaptability, and commitment to both his legal career and his community.
Growing up on the “Red Sox side” of Connecticut (which distinguishes it from the “New York side”), Tom attended Norwich Free Academy. The public high school — with a full campus and even an on-site museum — felt more like a small college. Tom thrived in that environment.
From there, the decision to attend Wesleyan University for college was an easy one. Wesleyan boasted a smaller school experience and had a reputation for academic excellence. At Wesleyan, Tom studied Government, finding a deep interest in governance and policy.
After graduating, Tom followed the advice of a family friend and his own growing curiosity, enrolling at the University of Pennsylvania Law School. There, he was drawn to the interdisciplinary approach and business focus of Penn Law, which aligned with his growing interest in the business side of law.
During his summer internships, Tom discovered his passion for corporate law, particularly working with startups like Lotus Development Corp. This early exposure further solidified his career path — and he went on to become a trusted legal department executive, providing leadership to several high-profile organizations navigating complex legal and business challenges.
We recently spoke to Tom about his journey through law school and his evolution into a top general counsel. His story not only reveals the value of curiosity and versatility, but it also offers insights into the qualities that make a great leader in today’s fast-paced legal world.
Tell me about your early career, just out of law school.
I joined Testa, Hurwitz & Thibeault in Boston, focusing on corporate law. I worked there for two years. But my wife, who is from the Chicago area, wanted to move back to the Midwest. So, just about two years after graduating from law school, I took a position with a firm in Chicago. But it wasn’t the right fit for me. They promised similar corporate work to what I had been doing at Testa, but it ended up being mostly broker-dealer work, which didn’t interest me. I started looking into other opportunities and received offers from a few large firms. Around that time, a recruiter called me about an in-house position at Baxter.
Were you excited to make the transition in-house at Baxter?
Initially, I wasn’t interested because I thought law firm life might suit me better, but I agreed to meet with the Baxter team. And the recruiter had emphasized that it wasn’t a typical in-house role.
I met with Marschall Smith, the associate general counsel, and had dinner with the team. Their focus on technology and their partnership with IBM intrigued me, especially since Baxter was selling computer systems to hospitals. So I decided to take the job.
I was brought on to handle contracting work for their hospital technology division, including large multihospital system contracts like one with the County of Los Angeles. I did that for about a year-and-a-half. Then, after that, I helped start a branch of the law department in California with another associate general counsel. This was for Baxter’s cardiovascular division, which later spun off into Edwards Life Sciences. I was there for about another year-and-a-half.
After about a year-and-a-half in California, Baxter decided to spin off their systems division into a joint venture with IBM. They asked me to return to help prepare the business for the spin-off. I spent about a year on that project. Although they offered me the general counsel role for the new entity, I declined and moved on to transactional work. Then, after that, I pivoted into a business position at another company.
How did your career shift to a business role?
My wife was working for a privately held company in Chicago, and the CEO approached me about running their small medical device division, Secure Medical. He wanted someone with transactional and operational experience, and I accepted. This was around 1990.
At Secure Medical, I ran the business, which included overseeing a manufacturing plant and sales team. We also explored acquisitions. However, in 1992, during the recession, the owner decided to exit the business, leaving me to consider my next steps.
How did you return to law after your stint in business?
I reached out to Marschall Smith, my former colleague at Baxter, who was then general counsel at American Medical International (AMI) in Dallas. He offered me a role as deputy general counsel. About six months after joining, Marschall left the company, and the CEO appointed me as interim general counsel. After a search for external candidates, he ultimately decided to make my role permanent. Eventually, AMI merged with National Medical Enterprises.
What happened after the merger?
I knew I wouldn’t remain GC since the merged company already had a leadership plan in place. This led me to return to Baxter. Back at Baxter, I was working under David McKee, who had been my boss in California. I became general counsel for the Renal Division, managing dialysis products. After two-and-a-half years, the GC of Baxter retired, and I was promoted to general counsel in 1997. I served in that role for the next six-and-a-half years.
In the years that follow, you landed in roles at some pretty high profile companies — Shering-Plough, United Airlines, Walgreens, Hertz and others. Would you explain that journey?
In 2004, I was recruited to become GC at Schering-Plough, a pharmaceutical company. I held that position until 2009, when Schering-Plough merged with Merck.
After the merger, I left the company and was recruited to become GC for United Airlines, where I helped negotiate a potential merger with US Airways. Shortly after, Continental Airlines proposed a merger instead, and we negotiated deals with both airlines simultaneously, ultimately merging with Continental. I was named GC for the combined company, but decided to leave shortly thereafter — taking nine months off.
Then I took the GC position at Walgreens, where I led the Alliance Boots merger in 2011. By the end of 2014, the CEO who had brought me in left when the incoming CEO from Alliance Boots took over.
Coincidentally, the former president of United, who had recently become CEO of Hertz, reached out to me out of the blue. Hertz was in turmoil, dealing with an SEC investigation and the firing of its previous CEO. He asked me to come on board as the chief administrative officer, a role with significant responsibilities, with a primary focus on navigating the SEC investigation. My role included overseeing HR and other departments, and I resolved the SEC investigation quickly.
After that, I took the role of executive vice president and GC at Aetna. Soon after I joined, we tried to acquire Humana, but the government blocked the deal. We then pivoted and successfully negotiated a merger with CVS. I stayed through the merger process but left after two-and-a-half years, thinking I would retire.
But you didn’t retire, did you? You ended up at Tenneco.
That’s right. While I was mentoring Brandon Smith, a younger lawyer and the GC of Tenneco, he decided to leave for a new role (editor’s note: Brandon Smith left Tenneco to become GC with agribusiness leader CHS Inc.; here is a link to our Q&A chat with Brandon: https://www.everslegal.com/2019/08/brandon-b-smith-senior-vice-president-general-counsel-and-corporate-secretary-at-tenneco/.) He recommended me to his CEO, who asked me to join to address challenges and groom two internal candidates for leadership. During my time there, we sold the company to Apollo Global Management, and I entered my second retirement.
Your second retirement didn’t take either, did it?
Not exactly. A former colleague from Aetna, Christin Bassett, who had been named interim general counsel at Rite-Aid, reached out. She asked me to help her handle the company’s challenges and prepare for bankruptcy. I joined Rite-Aid in June 2023 as executive vice president and chief legal officer. And we filed for bankruptcy in October.
During my time at Rite-Aid, we navigated three major government investigations and resolved litigation with the FTC, DOJ and states over opioids. We also managed bankruptcy proceedings, sold numerous stores and transitioned the company to new ownership under bondholders. I left after we confirmed our emergence from bankruptcy earlier this year.
Out of all the in-house positions you’ve held, which one stands out the most to you and why?
The Schering-Plough experience stands out as the most memorable and influential. It was a tumultuous yet rewarding role. The company was undergoing major challenges, including government investigations into marketing and billing practices, an SEC consent decree for selective disclosure and an FCPA settlement. Despite the chaos, I worked with incredible lawyers and learned invaluable leadership lessons from the CEO, Fred Hassan.
Schering-Plough was an intense environment with many moving parts, but it taught me how to lead effectively under pressure. Fred Hassan’s leadership style inspired me and helped me grow as a people leader. Additionally, we executed a major acquisition of Organon Biosciences, which laid the groundwork for future successes, including the development of drugs like Keytruda.
What do you love most about being in-house and serving as a GC?
Being in-house allows you to not just be close to the action, but to truly be part of it. A good GC deeply understands the business and its intersection with legal issues, which enables you to anticipate problems, offer proactive solutions and contribute to strategic decisions. It’s a level of involvement you don’t get in a law firm.
As a GC specifically, I love the people side of the role — developing others, helping them become better lawyers and business partners. Early in my leadership journey, I wasn’t confident, but as I gained experience, I became a better leader and found the process of managing and mentoring people incredibly fulfilling. I’m especially proud of those I’ve mentored who’ve gone on to become GCs themselves.
Did you have any mentors during your legal career you’d like to mention?
Yes, I had several key mentors. Marschall Smith was a significant influence early in my career. He taught me the importance of immersing myself in the business by interacting directly with clients and understanding their needs. He would often say, “Get out there,” and he was right — being visible and engaged is invaluable.
Fred Hassan, the former CEO of Schering-Plough, has also been a mentor and remains someone I consult for advice.
Another mentor is Mark Bertolini, the former CEO of Aetna. Though we didn’t work together for long, we developed a close relationship while navigating major corporate events like the Humana and CVS mergers. Both lawyers and CEOs have played important roles in my growth.
What are some things you like to do for fun?
We have dogs and are very involved with animal welfare through the Humane Society of the United States. We’re also big boating enthusiasts, spending time on the water. We lived in Maine for 13 years and now enjoy life on Lake Michigan and Ponte Vedra Beach. Boating and sailing are key hobbies, though I’ve shifted more toward power boating as I’ve gotten older. We love to explore, and we recently took a week-long boat trip from Boston to New York, stopping in places like Newport.
What advice would you offer to new GCs or young lawyers aspiring to land a GC role one day?
First, embrace Fred Hassan’s mantra: “Listen and learn.” Effective leadership starts with being curious — not just about legal issues but about the business, strategy and what makes everything work. This “restless curiosity” has helped me move across industries successfully.
Second, develop emotional intelligence. A good GC remains calm under pressure, thinks three steps ahead and solves not just today’s problem, but also the one looming years down the road. For example, sometimes you need to slow things down to ensure long-term success, even if it frustrates businesspeople in the short term.
Finally, understand that being a GC isn’t just about advising from the sidelines. You need to be a true partner in decision-making, take accountability, and ensure your advice is actionable and aligned with the organization’s goals. This builds trust and ensures your voice carries weight.
What’s next for you in your career and life?
I might retire, though my wife doesn’t believe me. I’m focusing on nonprofit work, particularly with the Humane Society of the United States, where I’ve been on the board and served as co-chair during a challenging period of governance reform. I’m also involved with smaller nonprofits and organizations like CPR (International Institute for Conflict Prevention & Resolution), which promotes alternatives to litigation.
In addition, I split my time between northern Michigan in the summers and Florida in the winters. We’re moving to Ponte Vedra Beach, near Jacksonville, after previously living in Naples and spending some time in Sea Island, Georgia. If anyone’s looking to buy a house in Sea Island, let me know!