Matthew Power is a study in risk and redemption. The 49-year-old Boston insurance man – he is executive vice president of Lexington Insurance Company, the nation’s premier excess and surplus carrier— has been well acquainted with the concept since his days as a youth on the streets of West Roxbury during Boston’s bruising busing crisis.

Those who have followed Power’s career say he knows a good risk when he sees one—whether it’s insurance policy protection for invasive surgical devices, for earthquakes, or for the storm of the century. “We live in a world of risk,” he says in an interview recently in his downtown office on the 18th floor of 100 Summer Street in Boston. “Recognizing the imbedded opportunity often inherent in risk is the basis for innovation and growth.”
Speaking in his aerie office above Boston, Power talked briefly about his growing up days in West Roxbury during days of trouble for the city, his neighborhood, and himself. “When the crisis took hold, West Roxbury, like many neighborhoods, was severely impacted.” As was Power himself. “In truth, the students were the sacrificial lambs of the busing crisis, as education was overshadowed by the turmoil and constant protesting that went on across the city.”
Power, a man with close family ties to Limerick, declines to amplify on the impact on him of that tumultuous period, only to say that he bounced around four high schools, then dropped in and out of college before graduating in 1989 from The University of Massachusetts.
Despite the challenges, Power showed academic promise along the way. A voracious reader from adolescence and intellectually curious, he consumed Dostoyevsky, Hesse, and, particularly, Shakespeare, “who,” he says, “spoke to me of every aspect of life, love, success, and failure.”
Those Shakespearean lessons about life and love came into fruitful reality when in his early ‘20s he was introduced to a stunning beauty named Margaret Callinan, who had emigrated from Limerick, the birthplace of his paternal grandparents. Margaret—traveling to Boston with Power’s Limerick cousin, joined the nursing staff at Brigham & Women’s Hospital.
“I can remember the first moment I saw her,” says Power. “It was lights out for me. She was beautiful, intelligent, and extremely well grounded. I knew right away that I wanted to spend the rest of my life with her. Looking back, I may have been somewhat of a tough sell for her! Margaret took some convincing.”
He and Margaret were married 22 years ago. They have two daughters, Caitlin, 16, and Samantha, 14, and live in West Roxbury on the same block where Matthew grew up, a stunning transition from his life in the neighborhood almost 40 years ago.
One of five boys growing up in a neighborhood in St. Theresa’s parish, where practically every father was either a cop or a politician, Power describes his childhood as a mix of thrill and anxiety given the society around him. The Power household, with a dominant father, was patriarchal, but Catherine (Crehan), with ties to Cork, held sway as mother and homemaker, even if she often felt as if she were herding cats. “She had to manage a good deal of chaos with five boys and their cadre of friends and cousins. Lots of scraped knees, black eyes, and calls from teachers,” says her son.
In many ways, Matthew is the image of his father, a man personified by his work ethic and entrepreneurial spirit. “He was entrepreneurial and very much a risk taker. He had an incredible work ethic. Still, for my Dad, his family and his faith came first.”
Once settled back in his old neighborhood, Power began the process of raising a family and building his career. “I am proud of the fact that I stayed in the neighborhood, to make a difference here, to make West Roxbury a better place,” he says, having most recently led a fundraising effort among his colleagues in Boston’s Financial District, which raised hundreds of thousands of dollars in support to build a new YMCA facility on Centre Street.
Despite increasing personal and professional success, Power carried with him a self-inflicted diffidence over his often-interrupted high school and college education. It bothered me tremendously,” he says, noting he was surrounded in business by academic world beaters. “I felt as though I had let myself down during those years in terms of academic focus.”
Academic redemption would come for him came at the in the halls of Harvard Business School where he was accepted into the prestigious postgraduate General Management Program in 2005. He would emerge from that experience with a new perspective on leadership, and a newfound confidence in his ability to perform at a very high level.
Born again academically, Power maximized his innate street sense and integrated it into his business sense, which by then had taken him from the Liberty Mutual and Kemper insurance companies, where he began his career, to the high rungs at insurance giant AIG, which he joined in 1993 as National Accounts Regional Director. In 2000, he was promoted to Northeast Regional Vice President, and two years later, he was named executive vice president of AIG’s Domestic Brokerage Group, with responsibilities for the East Coast and Canada, or about $7 billion worth of business.
In 2006, Power was named president of Risk Specialists Companies, Inc, a Chartis US subsidiary. That same year, he also took on his position at Lexington Insurance, under the AIG umbrella. The Risk Specialists Companies provide direct, local access to Lexington Insurance’s range of property, casualty and specialty insurance products and services.
Throughout the years, Power was the beneficiary of a world class insurance education as part of an organization led by AIG CEO Maurice (Hank) Hank Greenberg, a legendary executive. “Mr. Greenberg believed in placing young talented people into the deepest end of the corporate pool where they would quickly learn to sink or swim,” he says in appreciation of having the option of drowning. “The company created a culture to thrive.” Power clearly did well in his lessons. “I had learned some valuable survival skills growing up as a young man in Boston,” he adds. “You can’t underestimate the value of those tough lessons in life or in business.”
In the insurance business, risk is measured, says Power. “To win requires a willingness to take risk and the confidence in your own decision-making ability,” In short, the foresight to price risk correctly, an instinct for good communication, and the vision to lead. “And you better lead in a way that respects people,” adds Power. “You have to care about the people you’re charged with leading if you want them to follow. Poor leaders attempt to manage through intimidation. There’s a big difference between management and leadership. True leadership requires vision, character, and compassion for others.”
Power and Margaret, still a nurse at Brigham and Women’s, remain loyal to Ireland, visiting once a year to catch up with Limerick friends and relatives. “We want to make sure our children have an appreciation of their mother’s background. It is an important part of their heritage.” It is an enduring spirit with Matthew Power, as well. He is involved in Irish causes, chief among them the American Ireland Fund, a philanthropic network that supports worthy ventures of peace and reconciliation, and arts culture and education throughout Ireland.
“Ireland has undergone enormous change over the past 30 years, says Power. “Infrastructure improvements that have taken place over the last decade have improved accessibility and the ability to move people and products throughout the country. The financial crisis has clearly taken its toll on many of the island’s social constructs. The Irish healthcare system, in particular, has suffered from immense stress and lack of available public funding.”.
During last month’s visit to Boston, Irish prime minister Enda Kenny was the guest of honor at a private dinner at Boston’s Four Seasons Hotel hosted by the Ireland Fund. About 30 of Boston’s leading business executives attended, and Power was among them. “It is incumbent upon people who have done well,” he says, “to remember where they came from and support those things that can make a difference in people’s lives..”
Power also serves on the boards of the New England Council and the Greater Boston Chamber of Commerce, and sits on the Dean’s Advisory Board at the University of Massachusetts College of Management. He previously served on the boards of the Greater Boston YMCA and HopeFound.
Power clearly hasn’t forgotten where he came from—his roots and the stops along the way to 2012. His office walls and shelves are adorned with images underscoring a busy, successful life, pictures of him with Hilary Clinton, Ted Kennedy, John Kerry, Tom Menino, and Scott Brown. He is an avid New England Patriots fan, and his office shows it with team memorabilia like a signed Tom Brady jersey to framed photos of Adam Vinatieri and Tedy Bruschi.
“To have had all these experiences in my career and in my life, given the challenges I faced as a young man, I am truly blessed,” he says today. “What I’ve learned,” he says, “is that you have to constantly challenge yourself and welcome opportunities to get outside of your comfort zone in order to grow and be successful.”
Matthew Power’s life today is testimony to the fact that one can survive risk with faith, savvy, and endurance to become a sure bet on those actuarial charts.
Greg O’Brien is president of Stony Brook Group, a publishing and political/communications strategy firm based on Cape Cod. The author/ editor of several books, he writes for various regional and national publications, and is a regular contributor to the Boston Irish Reporter. Fittingly, he wrote this profile on a train from Dublin to Belfast on a recent trip to Ireland.