The Lessings

A Family of Innovators, Part III: 1980-Present

                                       THE MANSION                                               Photo courtesy of The Lessing Family.

                                       THE MANSION  
                                         Photo courtesy of The Lessing Family.


See Parts I and II.


Tight-knit Irish clans are often guided by an invisible hand. When I asked Jack Lessing, the Chairman of Lessing’s, when the family first got into the retail restaurant business he answered, “It wasn’t until 1977. My mother, a devout Irish Catholic, never wanted the family to sell liquor.”

But in 1977, a friend of Jack’s told him that the only bar in Breezy Point, (the now world famous New York Irish Police and Fireman’s community destroyed in Hurricane Sandy) was for sale. The Bay Terrace Bar was the only pub in a community of 3,800 homes occupied by New York’s Firefighters and Policemen.

“It was a gold mine,” Jack says. “We used to sell 250 cases of beer on a Saturday night. That was a lot of beer in 1977.”

Lessing was hooked. The family began to diversify beyond contract food service into the retail restaurant business at just the right time. Contract food service, a business that Lessing’s had originated and built for 40 years, was becoming a commodity business by the late 1970s. Once the industry saw the food service market niche that Lessing’s had created, everyone got into the business. Big corporations like Servomation and the Canteen Corporation joined hundreds of small independent contractors in increasing competition until there were 8 or 9 bids submitted on every account.

“Our B&I business was still strong because our customers were loyal, but it became harder and harder to make a profit in contract food service,” Jack says.

He saw how the cash flow from the Bay Terrace Bar could supplement the reliable but slim margins in contract food service, so he began to diversify into retail restaurants.

 The Main Street Innovation

Prior to the 1980s, restaurant chains were not well received on Long Island, so few national chains bothered to open units in

 Photo courtesy of The Lessing Family.

one of the nation’s most densely populated suburbs. Long Islanders seemed to feel more comfortable with local restaurants. The Lessings knew that any restaurant they opened must feel like a “local joint”. They watched the success of the Bay Terrace Bar and waited for the Lessing innovation impulse to kick in. Eventually, they decided to open cafes that would serve the local clientele along Montauk Highway, the road that had become the Main Street of Long Island’s south shore villages. They would locate them in historic town buildings that the long-time residents were familiar with.

In 1980, the Lessings opened their first Main Street restaurant in the historic post office building that had served the town of Babylon for many years. The Post Office Cafe was immediately seen by Babylon customers as a local place where they were comfortable. It was an instant success and has been going strong for 35 years.


By the 1980s, the Main Streets along Long Island’s South Shore were becoming gentrified by the growth of more modern shopping centers opening on the Sunrise Highway.

With The Post Office Cafe booming, the Lessings migrated east along the Montauk Highway to the little town of Bay Shore and opened their second Main Street Restaurant in the town’s original fire house. The youth of Suffolk County instantly made the Firehouse the most popular young club on all of Long Island. Thirty years later the Lessings purchased the historic Southside Hotel, Bay Shore’s original “local joint” across the street from the Firehouse.

History will record that Lessing’s Main Street restaurant concept ignited a revival movement that has brought these old historic Long Island Main Streets back to life.

When the original library closed in Farmingdale, Long Island, the Lessings bought the building and opened another Main Street restaurant, The Library Cafe. Each restaurant’s success drove the Lessings along the same strategic path; find and purchase historic Long Island buildings that were icons to the local clientele. They opened Maxwell’s on Main Street in Islip and bought the Huntington landmark, Finnegan’s, perhaps the most “local” of all their Main Street pubs and cafes.


During the 1970s and 80s, Lessings was also operating over 100 concession locations at state, county, and town parks from Montauk to Long Beach. They were the biggest picnic caterers in the State, at times feeding as many as 10,000 people. They operated the concessions at the now legendary Hechsher State Park, Eisenhower Park, Bethpage State Park, Sunken Meadow, and Tobay Beach.

 Fine Dining

In the ’90s, the Lessings made another strategic decision when they purchased the most historic and iconic building of all, The Three Village Inn in Stony Brook, Long Island. Built in 1751, The Three Village Inn had served as a summer house, a Women’s Exchange, a simple tea room, and a fine country inn. In this historic location, the Lessings expanded beyond their pub and cafe style Main Street restaurants to enter the fine dining segment with their now famous Mirabelle restaurant.

THE VIEW!         Photo courtesy of The Lessing Family.

 Photo courtesy of The Lessing Family.

Combining Innovations

The Saxon Arms restaurant in Oakdale enjoyed the best waterfront view of the Great South Bay anywhere on Long Island. Lessing’s bought this local favorite, changed the name to (what else?) The View, refurbished the building and the menu, and now operates the most popular dockside restaurant on Long Island’s South Shore.


The insight to appeal to local tastes by instantly becoming part of the local cultural heritage was a brilliant innovation. During the 1990s, the Lessings began a rapid expansion into the catering business by utilizing the same innovative instinct that began to serve them so well in retail restaurants.

Long Island was comprised of rural farms and small seaport villages until the turn of the 20th century when the great family fortunes created by the industrial revolution built vast estates on Long Island. More than 1200 grand estates were built along the North Shore’s “Gold Coast” of Great Gatsby fame. Many of these mansions remain in existence throughout Long Island to this day.

By the 1950s, grand-estate living was going out of style, and many of the mansions were turned over to colleges, charities, and religious orders. Knowing that these estates were considered the best addresses in many local towns and villages, the Lessings decided to lease, license, or buy them for catering locations. What local bride would not want to be married in the grandest estate house in her village?

Lessing’s now offers Long Island brides the opportunity to hold their wedding reception at The Bourne Mansion, The Chateau at Coindre Hall, The Mansion at Timber Point, The Mansion at West Sayville, and The Estate at Three Village Inn, to name just a few. These iconic locations have become so popular that Lessing’s now caters more than 850 weddings a year!

 The Present

Today, Lessing’s operates 110 Contract Food Service locations in Education and in Business & Industry, six Main Street restaurants, two fine-dining restaurants, 14 catering facilities, a country inn and two new Blaze Fast Fire’d Pizza franchises. The company employs more than 1,500 people, and is now ranked in the top 40 food service companies in the U.S. This highly complex and diversified food service company is still managed by the present generation of Lessings.

Author’s Note
In this history, I have attempted to reveal the secrets of longevity and consistency that enabled Lessing’s to survive and thrive for 125 years in the world’s most competitive food service market. How did each generation attract the next generation into the business? How did they survive ever-changing tastes, a volatile commodity market, two world wars, the Great Depression and the Great Recession, inevitable family squabbles, an increasingly contentious legal environment, and stiff competition from well-financed public companies? What was the magic? Each Lessing generation, from Maxwell to the present, never took survival for granted. They responded to changing market conditions with CREATIVE INNOVATION.


Learn more about Francis Bennett at www.francisbennettcreative.com.


                 JULY ISSUE    2015

                 JULY ISSUE    2015