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A common turn of phrase when partners switch law firms is the broader “platform” or “deep bench” provided by their new home.

For Jeffrey Pagano, until recently a partner at Crowell & Moring in New York and former co-head of the firm’s labor and employment practice, his new firm is located within the twin forks of Long Island, and the only benches are those lining Main Street outside his office.

Pagano’s decision to leave Big Law on April 27 was driven not by a desire to ease into retirement, but a yearning for a better way to live out his golden years, both at work and at home. And Pagano, an avid drag racer in his spare time, knows a thing or two about driving into uncharted territory.

“You get to a point where you start to appreciate another side to life,” said Pagano (pictured right), looking out from his hotel room over the Port of San Juan, where he landed Thursday, a day after Puerto Rico’s bankruptcy. “I’d always considered myself a 2,500- to 3,000-hour [a year] type guy. I wanted to continue on—but at what price?”

The Big Law grind leads many lawyers to leave large firms for other endeavors, but Pagano enjoyed his practice and didn’t want to give it up. Instead, he saw an opportunity presented by the “gig economy,” a new position that would allow him to keep the clients he accrued during his 40-year legal career and permit Pagano to work at a time and place of his choosing.

“If I could achieve client objectives and my professional aspirations, what difference does it make where I am located?” Pagano asked. “The gig economy allows complete flexibility and excellence from both perspectives. And it allows both success and happiness.”

At 66, divorced and with two grown sons, whom Pagano credits with giving him the courage to make such a bold career move, he embarked on a new journey.

A day after resigning from the partnership at Crowell & Moring, Pagano left his office in midtown Manhattan for a new gig 100 miles east at Twomey, Latham, Shea, Kelley, Dubin & Quartararo, the largest firm on Long Island’s East End. Pagano knew name partner John Shea from East Hampton High School, a public school in the New York town of the same name that their sons attended.

The roughly 30-lawyer Twomey Latham is similar in size to King Pagano Harrison, a New York- and Washington, D.C.-based health care and labor litigation boutique that Pagano started in 1991 until Crowell & Moring acquired the firm in late 2006.

Pagano has fond memories from both firms, but it was at King Pagano Harrison where he really enjoyed the camaraderie and collegiality of working in a smaller shop.

“I felt the whole firm,” Pagano said of King Pagano Harrison. “And that’s nothing against [Crowell & Moring], it’s just naturally harder to have that at a large firm. It was a nice place with nice people. This [move] was more about the type of environment where I wanted to practice.”

At Crowell & Moring, where his good friend and racing companion Keith Harrison is still a partner, Pagano set up a small office in East Hampton. The remote space, which he took out above the now-shuttered Dreesen’s market, allowed him to see his sons grow up.

“Having an [East Hampton] office was crucial because the boys could see that I actually worked as they would stop by the office as they walked home from school each day,” Pagano said. “I did not want to intrude in our home life or be at a computer at home ignoring their needs.”

Pagano, who had a working class upbringing in Asbury Park, New Jersey, bought a house in East Hampton in 1996. After his divorce in 2001, Pagano threw himself into work, but continued shuttling between East Hampton and Manhattan, while also traveling for his national labor and employment practice. Having grown up near the Jersey Shore, Pagano wanted his two sons to have a similar upbringing in a small town by the ocean, away from the city.

His home is not far from the seaside mansions of the top 1 percent—few things on the East End are—but Pagano lives inland among the locals, the teachers, firefighters and police officers. What started as a summer home eventually became his primary residence, although he kept an apartment in Manhattan. With his youngest son off to college in 2013, Pagano closed Crowell & Moring’s East Hampton outpost and returned to working full-time in New York.

The American Lawyer reported earlier this year on Crowell & Moring shuttering several offices as the firm engaged in merger talks with New York’s Herrick, Feinstein. Those discussions ended last month and Pagano said he stayed away from getting involved in the talks.

“My leaving [Crowell & Moring] had nothing to do with Herrick,” he said. “I still aspire to greatness, but I want to do it in a place where I don’t have to sacrifice my life. The biggest challenge in leaving [Manhattan] is ego.”

Pagano admits that for part of his career he was obsessed with status. He wanted that Crowell & Moring corner office at Madison Avenue and 57th Street, with a view to the southeast. He was initially skeptical about how a large firm environment would help his clients—Crowell & Moring’s former chairman Kent Gardiner wrote as such in a 2007 op-ed for Legal Times—but he took to his new colleagues. (Jeffrey King, another former name partner at King Pagano Harrison, left Crowell & Moring in late 2012 and now lives in Delray Beach, Florida.)

A few years ago Harrison (pictured right with Pagano) helped Pagano revive a childhood interest in fast cars, something that he described to the New York Law Journal in 2013. He doesn’t feel old, and his street racing hobby—one that has taken him around the country—doesn’t allow him to rest on his laurels. But even after rediscovering that passion, Pagano felt that something was missing.

“What East Hampton and my boys gave me could not be replaced by money or the thrill of New York,” Pagano said. “Client work remained [a] passion, as it does today, however the life beyond work died, which I regretted.”

That brought Pagano to his decision to leave Crowell & Moring. A few weeks ago a client in Little Rock, Arkansas, asked Pagano why the best lawyers always have to be based in New York. Pagano liked to tell clients that it was because of the proximity to three different airports. But he could still drive to any of them from East Hampton. He could not ignore the opportunity presented by Twomey Latham.

While the firm did not have a labor and employment practice, Twomey Latham was unburdened by the overhead that comes with being in the Am Law 100, and it also has a stable of deep-pocketed clients. Pagano’s clients, such as TOTE Inc., Tote Maritime, SSA Marine Inc. and Puerto Rico Terminal LLC, are the carriers and terminal operators he’s now advising in Puerto Rico as they negotiate with stevedores and longshoremen.

All are coming with him to Twomey Latham, said Pagano, who is in San Juan preparing for a National Labor Relations Board trial next week. He’s already heard from some of his former colleagues, inquiring as to whether he wants to rebuild a King Pagano Harrison-type labor and employment group within Twomey Latham, where Pagano now splits his time between the firm’s offices in East Hampton and nearby Riverhead, New York.

Further out on the East End, between Amagansett and Montauk, there is a long stretch of highway on Route 27 uninterrupted by cross streets that Pagano can use to “practice” racing. He owns a 1972 Chevrolet El Camino—with a new chassis—and has already signed up for Drag Week 2017.

Each morning, Pagano tries to take a trip to the beach, breath the sea air, look out at the ocean and think. And more importantly, he’s happy.

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