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Fast Track

A Walk on the Tall Side

The trajectory of 6-foot-5-inch Damon Hart ’99, a legal, business, and community wunderkind, has been meteoric—and he’s not done yet.

Photographs by Adam DeTour

Fast Track

A Walk on the Tall Side

The trajectory of 6-foot-5-inch Damon Hart ’99, a legal, business, and community wunderkind, has been meteoric—and he’s not done yet.

Photographs by Adam DeTour

The 185-year-old Boston Public Garden is a powerful people magnet. Residents and tourists alike are attracted to it—drawn in to escape the hustle and bustle of the city at lunchtime, to admire the famous tulip beds in season, to skim the surface of the pond in iconic swan boats, or, like many, to capture the romance of the setting as a backdrop for marriage proposals.

But, look closer and you’ll see others who’ve sought respite from hectic offices or crowded restaurants to have private conversations. That’s why Boston College Law School alumnus Damon Hart, who was named Executive Vice President and Chief Legal Officer of Liberty Mutual Insurance Company earlier this year, and BC Law graduate Steven H. Wright ’81, then a partner in the global law firm of Holland & Knight, met there twenty-three years ago. Their talk that day—under a clear, sunny sky on a bench near the future site of the 9/11 Memorial—set Hart on the path that has led him to the top ranks of one of the world’s largest corporations. In fact, Hart has been named Secretary of Liberty Mutual, effective in January 2023, and will oversee governance of the company’s board of directors in addition to his current responsibilities. 

In 1999, Hart was on the threshold of graduation from BC Law School with a pocketful of enviable job offers when he received the call from Wright to meet in Boston Public Garden. Wright, who is African American, was seeking new recruits for Holland & Knight, and he was especially interested in candidates who could add diversity to the prestigious firm’s professional ranks.

“I had consulted my networks around town, and I learned about Damon from another BC Law graduate, Chuck Walker,” Wright recalls. Charles “Chuck” E. Walker, Jr.’78 was chairman of the Massachusetts Commission Against Discrimination and a highly regarded figure among Boston-area Black lawyers, and he urged Wright to speak with the promising young law student.

Wright, who is now the Senior Vice President and General Counsel of the Federal Reserve Bank of Boston, says he was glad he took Walker’s advice. “Damon was one of the best graduating law students I had seen,” he says of their first meeting. In addition to being “extremely intelligent with a high level of drive and desire,” Wright says Hart also “had a thoughtfulness about him, a graciousness” that made him stand out.

For his part, Hart was equally impressed by his exchange with Wright; he declined his other offers to join Wright at Holland & Knight, where he was immediately successful, making partner earlier than was typical at the firm and spending eleven years there representing major clients that included Coca-Cola, Marriott, Ritz-Carlton, and BJ’s Wholesale Club, among others. 

The experience “really helped me understand how different businesses operate and how different businesses make money,” Hart says. “I also got to learn about the relationship between the business and the legal department, and not all of those relationships are good. One of the things I really value about Liberty Mutual is that it’s a really true partnership between the business and the legal department.”

Reflecting on his time at Holland & Knight, Hart says he also learned the value of mentorship in building a career, beginning with his initial meeting with Wright. “He literally told me what the next five to ten years of my life would look like if I joined him, and he fulfilled every one of those promises,” he says.

“I’m very grateful for the time I got to practice with him very closely and learn a lot about relationships and about how important your reputation is, especially in a ‘small town’ like Boston.” Hart says he benefited from “seeing how [Wright] cultivated a really sterling reputation for being creative, getting things done, and being a person of integrity.”

However, Holland & Knight was just the beginning for Hart. He would move through stints at two more highly respected firms—Ogletree Deakins and Littler Mendelson—before joining Liberty Mutual Insurance Company in 2014 as vice president and assistant general counsel and rising through a series of positions of increasing responsibility before his promotion to the top legal job this year. In his new role, Hart oversees a sprawling staff of 2,100 in nineteen countries to serve the insurance giant’s legal interests around the world.

“He’s obviously smart, and he had a significant amount of legal experience in the law firms, but there were other attributes: He’s a great listener, he’s very thoughtful. His level of empathy is excellent.”

Jim Kelleher, recently retired executive vice president and chief legal officer of Liberty Mutual and Hart’s predecessor

Early in his tenure at Liberty Mutual, he caught the eye of the man he would eventually succeed—Jim Kelleher, the recently retired executive vice president and chief legal officer. “He’s obviously smart, and he had a significant amount of legal experience in the law firms,” Kelleher says of Hart, “but there were other attributes: He’s a great listener, he’s very thoughtful. His level of empathy is excellent.” As Kelleher watched Hart develop and take on complex legal and organizational challenges, he says, “it became clear that he was a true leader.”

Kelleher’s assessment wouldn’t have surprised Jerome Revish, senior vice president, digital transformation, of Cardinal Health in Ohio, and Hart’s cousin. It fits with everything Revish has known about Hart since they were children. Although they are related, he says, he understands from his own corporate experience the significance of “seeing, not just my cousin, but another Black man at that level, at that C-Suite level at a prominent company, because I know how hard that journey is, and I know that there aren’t hundreds of folks sitting in his chair.”

Indeed, Hart’s promotion makes him a member of an extremely small club. In early 2022, there were sixty-two Black attorneys in the top legal job at Fortune 1000 companies, including Hart, according to statistics compiled by the Black General Counsel 2025 Initiative, which seeks to raise the number to 100 by 2025.

In 2017, when the initiative was founded, there were just thirty-eight Black chief legal officers in Fortune 1000 companies. Three years later, in 2020, the number had crept up to fifty, and though the numbers have grown, the goal of 100 Black chief legal officers in the next three years will be “really challenging,” says the initiative’s co-founder, April Miller Boise, chief legal officer of Intel Corporation. Nevertheless, she adds, “it’s important to set aggressive goals, because if we don’t set those goals we’re not going to get there.”

Longtime friends say Hart’s accomplishment is the natural result of who he is and how he has conducted his life over the years. Even as an undergraduate at the College of the Holy Cross, where Hart played varsity basketball, he stood out for his seriousness of purpose, says Brian Lockhart, a classmate and teammate. “Damon had a different level of serious academic rigor than most of us on the team,” recalls Lockhart, the senior vice president of original content and ESPN Films at ESPN, Inc., the international cable sports network. “He had a clear vision of how he operated when it came to academic success and achievement.”

A BC Law classmate, McCray Pettway, says she has long been impressed by the way Hart balances his competitive drive with humility. “Damon was always in awe of those who came before him, trying to learn all he could,” she says. But, in turn, says Pettway, who is now vice president and associate general counsel at Expeditors International of Washington, Hart also seeks to enhance the stature of his peers.

She notes that the 6-foot-5-inch Hart is often the tallest person in the room, but “Damon has a way of diminishing himself to make you bigger in the conversation. I’m 5 feet tall, and I’m fighting for every bit of the 5 feet,” she says with a chuckle, before adding in a more serious tone that “you don’t have to stand on your toes to talk to him. He’s trying to get closer to the person that he’s talking to so he can be attentive and fully present. That’s who he is.”

However, Pettway emphasizes that it is a mistake to misread Hart’s kindness. “Damon is fierce,” she says. “His motive is to win, but it is to win in a transformative way, and that’s the leadership you want. I suspect that’s the leadership Liberty Mutual identified in him when they promoted him from vice president to senior vice president to deputy general counsel and then announced their intentions to make him general counsel.”

Hart’s confident demeanor and concern for others have long been qualities that draw friends and colleagues to him. As an example, Pettway says Hart emerged as a leader during their first year at BC Law when a controversy arose over challenges by white students to a young Black faculty member’s credentials and rigorous grading. The situation was painful, she says, but Hart was a “healing” influence.

Hart led a group of Black students to speak to the professor to demonstrate their support for her, but he also worked to maintain relationships with “colleagues who were not Black,” Pettway says.

In recalling the incident, Hart says it was important for students to move beyond that moment. “I kept saying [to Black students], we can’t let this spiral out of control and spend all of our time worrying about their perceptions of us while they’re in the library studying. It would have been a tragedy if we would have let that derail our first year, which is so important in terms of solidifying your rank and the opportunities that flow from that first year. So, I just kept calling on the group to focus on why we’re here.”

Decades later, Hart, a former president of the Massachusetts Black Lawyers Association, continues to balance career objectives with service to others. He is a co-founder of the New Commonwealth Racial Equity and Social Justice Fund, launched in 2020 in the wake of the George Floyd killing and the onslaught of the Covid-19 pandemic to support programs that seek to address systemic racism in institutions throughout Massachusetts. Hart and his longtime friend, Damian Wilmot, senior vice president, chief risk and compliance officer at Vertex Pharmaceuticals, Inc., rallied nineteen of their fellow senior Black and brown executives at Massachusetts companies to raise more than $20 million from their respective corporations to fund the initiative. The fund’s longer term goal is to raise at least $100 million.

Another of Hart’s civic commitments is The Home for Little Wanderers, where he serves as vice chair of the Board of Directors. The organization, which began as an orphanage in 1799, now provides a wide range of services for children whose lives have been impacted by various kinds of social and emotional traumas. “It’s just such a powerful organization that stands in the gap for vulnerable families and children,” he says.

Hart’s passion for The Home for Little Wanderers is consistent with two of his traits that those who know him often cite—his commitment to his Christian faith and to his family. “I try to live out my relationship with Christ in a way that doesn’t hit people over the head. I try to live by that old adage that I’d rather see a sermon than hear one,” he says, adding that he tries to express his faith through his example, “especially these days when people are going through some profound things.”

“Damon has a way of diminishing himself to make you bigger in the conversation. I’m 5 feet tall, and I’m fighting for every bit of the 5 feet…[but] you don’t have to stand on your toes to talk to him. He’s trying to get closer to the person that he’s talking to so he can be attentive and fully present. That’s who he is.”

McCray Pettway ’99, classmate and longtime friend

Hart’s values were forged in the small western Pennsylvania community where he was raised. The City of New Castle has a population of less than 22,000 and is just a few minutes’ drive from the border with Ohio, where his late father worked for General Motors in Youngstown until his retirement. His mother, ironically, worked in Liberty Mutual’s New Castle office, as did Hart during the summer after his freshman year in college, as part of the maintenance crew.

Hart was the youngest of three boys. “I’m the baby, but I’m also the biggest, the tallest,” he says, laughing. And, they all loved sports. During summer vacations in high school, he recalls, “We would leave the house with a bag of balls and play a bunch of different sports. My older brother was a very good track athlete; he was a 400-meter runner, and he played football. My middle brother was a hurdler and played basketball and football.”

Football and basketball were where Hart focused his athletic energy in high school, and though he was recruited by Holy Cross as a football quarterback, he switched to basketball after his freshman year. “I had an itch to play basketball, so I walked on and made the JV team, and by the end of the season I was suiting up for varsity,” he says. In short order he became the starting forward for the Holy Cross team that played in the 1993 NCAA tournament.

Hart remains physically active. He plays golf with friends and is also a cyclist who rides in the annual Pan-Mass Challenge to support the Dana-Farber Cancer Institute. And, there are the dog-walks. “We got a Covid puppy, and she’s taken a liking to me, so I’m the primary walker,” he says. “On most weekends I take a long walk with a book on Audible or a podcast. I’m kind of a podcast king.”

And despite a hectic professional and civic schedule, Hart carves out time to spend with his family. He lives with his wife, Kathy, and son, Miles, nineteen, and daughter, Aveda, fifteen, in the Boston suburb of Brookline. Both his son and daughter are athletes, and Hart often travels with them for their school and club tournaments. The family also enjoys the vibrant arts scene in the Boston area, especially art films, live theater, and the museums.

But, Hart says, “We just kind of like to be with each other, to be honest with you. It doesn’t matter what we’re doing.” During the summer months, their time together is often spent at their vacation home in the Oak Bluffs community on Martha’s Vineyard. “There’s a long history of African American families being down there, which makes it more welcoming,” he says. “It’s just a really cool kind of magical place.”

Although Hart grew up in western Pennsylvania, he decided early in his career that he would make his home in Massachusetts, in part because of the extensive network of BC Law alumni, but also because of its central role in American history and notably African American history—particularly in connection to one of Hart’s personal historical heroes, the abolitionist Frederick Douglass, who gave some of his most powerful speeches in Boston. Excitement edges into Hart’s voice when he speaks of Douglass. “It’s meaningful to walk on the same ground that Frederick Douglass walked on,” he says. Hart says he admires the success of Douglass, the escaped slave who became one of his era’s greatest orators, in influencing a reluctant President Abraham Lincoln to support freeing enslaved Black people. “I think in my current role I see a parallel,” Hart says, “in that I’m in a role of influence in terms of the leadership of the company and the leadership of the community. And so, if I can influence the right decisions, I see that as part of my job.”