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When Connecticut law firm Day Pitney noticed a few years back that many of its high-net-worth and business clients were moving to Florida in search of warmer winters and lower taxes, it turned the potential challenge into a growth opportunity.
Faced with the possibility of losing those clients to local firms or working with them from afar, it decided instead to follow them, merging in 2016 with a small Palm Beach County trust and estates firm and gaining its first foothold outside the Northeast.
Another merger this year — with the boutique litigation firm Richman Greer — brought its Florida headcount to 22 attorneys in offices from Miami to West Palm Beach.
Responding quickly to the changing needs of a more demanding clientele has been a key to Day Pitney’s staying power, especially in the cut-throat legal market that’s emerged since the Great Recession of 2008, said Managing Partner Tom Goldberg.
Clients have become more sophisticated in their approach to working with outside counsel, he said, moving much of the more mundane legal work in house and demanding that outside legal firms “add value.”
“So you can never take any client relationship for granted,” Goldberg said. “We and other firms have to prove ourselves every day.”
Day Pitney is one of three of Greater Hartford’s largest law firms — along with Shipman & Goodwin and Pullman & Comley — that have recently marked their 100th year in operation, a milestone that is becoming harder to reach in an industry that has undergone tremendous change and consolidation, experts say.
“For a firm to reach the 100-year mark is really pretty significant,” said Jim Jones, a senior fellow at Georgetown Law’s Center for Ethics and the Legal Profession. “Especially today, when firms are being acquired and merging and disappearing … in this new competitive environment.”
After more than a decade of unprecedented growth, the legal industry “was turned on its head” following the 2008 financial crisis as businesses faced intense pressure to cut their legal costs, Jones said.
“All at once, clients were demanding efficiency and cost-effectiveness and predictability and, frankly, it caught a lot of law firms completely flat-footed,” said Jones, who co-authors an annual report on the state of the legal market. “We’ve seen 75- or 100-year-old firms that have gone out of business at breathtaking speed.”
Firms most successful in weathering the upheaval are “really being proactive in addressing these kinds of [demands] their clients have,” he said.
One opportunity for law firms in regional markets like Hartford is that clients are increasingly seeing the value of using smaller and midsized firms, he said.
“They’re realizing that there are really good lawyers even in smaller firms,” Jones said. “You don’t need to have a big prestigious Wall Street firm doing everything on your matter.”
Alan Lieberman, managing partner at Shipman & Goodwin, said his firm has stood the test of time by staying true to its core values — service excellence, integrity, collaboration and collegiality — while also embracing change.
He said the firm has remained competitive by adopting technology such as client portals and artificial intelligence to boost efficiency and accessibility, offering alternatives to traditional hourly billing and specializing in new areas — strategies echoed by the other two firms.
Lieberman pointed to the recent launch of the firm’s state attorneys general practice group, which he said answered a call from clients who were dealing with complicated compliance issues across multiple state borders.
Led by former Connecticut Attorney General George Jepsen and his former deputy, the group represents business clients facing enforcement actions by state attorneys general, in areas ranging from consumer protection and antitrust matters to environmental regulation.
If a client faces a data breach affecting customers in 15 states, the group can swoop in “like a SWAT team” to contact the 15 state offices and resolve the issue quickly, Lieberman said.
“It’s a perfect example of where a client’s needs dictated to us what we needed to do strategically as a firm,” he explained.
Bridgeport-based Pullman & Comley, which has an office in Hartford and recently expanded to Springfield, has also kept its competitive edge by developing new areas of expertise as Connecticut’s economy evolved, said Chairman James T. Shearin.
“I’m sitting in Bridgeport right now which in the ‘40s and ‘50s was the munitions capital of the world. That industry is gone and in its place have come other businesses, so as law firms we adapt,” he said. “You’ve got to remain on the cutting edge as the business and industry around you changes.”
He said one of the biggest shifts in the last two decades has been in the public-development arena. Having a hand in “pretty much every major development project in the state,” he said, the firm now specializes in public-private partnerships and incentive programs like Opportunity Zones, which promise federal tax breaks to developers building in distressed neighborhoods.
It’s also found new clients in emerging industries like alternative energy and medical marijuana.
Shearin, Goldberg and Lieberman also cited their firms’ strong commitment to community service, but agreed that the main driver of any prospering law firm is its people.
“Not only the hiring. It’s the training, it’s the retaining,” Shearin said. “I think we all share that common ingredient: The people make it work.”
Georgetown’s Jones said attracting, nurturing and keeping top lawyers is a tall order at a time when talent poaching from rival law firms is at an all-time high nationally. Non-compete clauses that are standard in other industries are considered a violation of ethics in the legal field, he said.
“Keeping a firm together [in this climate] requires a lot of attention not only to economics but also to culture,” Jones said. “You’ve got to make your people want to be there and give them good reasons for wanting to stay. I take my hat off to any firm that’s successfully done that for 100 years.”
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The Hartford Business Journal 2025 Charity Event Guide is the annual resource publication highlighting the top charity events in 2025.
Hartford Business Journal provides the top coverage of news, trends, data, politics and personalities of the area’s business community. Get the news and information you need from the award-winning writers at HBJ. Don’t miss out - subscribe today.
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