At first Michael built a modest home on property owned by an earlier settler. "I don't think you could call it more than a tent, for he built it without a floor and the chimney was built on the ground, and the fire place was built up with one side open and he lived a great many years without but a very few repairs," wrote a family member 150 years after the fact. But after ten years of relative squalor, records show that he acquired a larger tract and built a more handsome home, part of which is incorporated in a still-standing structure improved by his descendants. As time passed, Michael married and left a legacy of his own. His eldest son, Daniel, was eventually given the homestead, leaving a younger brother, Samuel, with nothing more than a three-acre plot.
His comparatively more humble estate did not squelch Samuel's ambitions, as he was destined to become among the wealthiest citizens of the booming port of Norwalk and its Wilton suburb. In 1779, in the thick of the American Revolution, and during a time that could be described as an economic recession, Samuel teamed up with his brother Sumner and a neighbor, Aaron Comstock, and opened a general store and warehouse. The new business was an immediate success. But during the Revolutionary War, Norwalk was burned by the British, and Samuel's store was looted by marauding Red Coats. He lost a mirror - at the time a high-end luxury item - and a cask of rum. Another tale has it that a cannonball flew through the premises, damaging the two-story building that stored commodities and produce from the neighboring farms, along with a substantial stock of molasses, sugar and rum from the Caribbean that were becoming mainstays of the colonies. The cannonball was recovered, and became a part of family lore, or so the story goes. Later records show that Samuel put a value on the damaged goods of 14 pounds, an appreciable sum for the time, but by no means a catastrophic loss.
During the stressful days of the Revolutionary War and its aftermath, Samuel found it profitable not only to expand his enterprise along the riverfront, but to invest in a seagoing vessel that would make trading expeditions to the Caribbean. Other merchants followed suit, turning Norwalk into one of the busiest seaports of the newly liberated colonies through which goods from the West Indies found their way to New York City and other northeast destinations.
Always interested in expanding his enterprise, Samuel bought out his two partners after the war. Later he underwrote a trading depot in Ballston Spa, some 150 miles to the north on the upper reaches of the Hudson River, assigning his former partners to manage the new location. The Ballston Spa depot became a regional distribution point for goods from Connecticut farmers.
Rum was beginning to blossom as a favorite of the colonists, young and old alike, and Norwalk became a town known for its heavy consumption of alcoholic beverages, with boys as young as 14 commonly found in an intoxicated state by local constables. Samuel capitalized on the new liquor craze by ensuring that his vessel was filled with fine Jamaican rum before its departure from the East Indies to the the newly formed United States. Hardly a sale in his store was made without a dram of liquor being included in the purchase. The dark side of this prosperous rum trade was that overconsumption of alcohol would eventually be the downfall of several of Samuel's descendants.
As much as his prosperity was seen as a sign of God's blessing, Samuel endured the tragedy of the early deaths of several of his children, an all-too-common phenomenon of a time when cyclical outbreaks of small pox and consumption were sure to take their toll. It was under such circumstances that one of his promising sons, Lewis, was given the responsibility of running a general store. The store flourished until Lewis's untimely death in 1811 at age 25, only a few months before that of his father. Not much is known about Lewis's short life, except that he kept slaves, and married his brother Nathan's wife after Nathan passed away. Lewis fathered three children before he died, and Samuel, perhaps grief-stricken by the loss of his son, left each of them $2,000 - the equivalent of about $35,000 today. One of those children, George Lewis Middlebrook, was the beneficiary, not only of money from his father's estate, but of land as well.
Not content with the small-town atmosphere of Wilton, George Lewis and his brother, Aaron Legrand, moved closer to New York City, where occupations other than farming held sway. They settled in Elizabethtown (now Elizabeth), New Jersey, where Aaron established a retail outlet that stocked every kind of luxury and staple item imaginable, from fine art work to fabric, furniture, men's suits and pots and pans. It was there that George Lewis ' s youngest son, Charles Trinder Middlebrook, was born. George Lewis himself partnered with a Middlebrook uncle to trade goods in New York City. He later moved with his family to Brooklyn, and died there in 1841, his wife quicky remarrying and garnering enough resources for her son, Charles Trinder Middlebrook, to be educated abroad. After his graduation from what is today's Princeton University, Charles married Emily Congdon, the daughter of a prosperous Brooklyn merchant and cultural impresario, and was almost immediately thereafter sent to the front lines in the American Civil War. His service, however, was short, and after the war, he was able to establish a successful legal practice in Brooklyn, dealing with matters as diverse as estate liquidations and labyrinthine liability cases. In the 1890s, after moving to Staten Island with his wife and her parents, Charles and Anna Congdon, his cousin, Aaron Legrand Jr., and his three children, he established an office at 20 Nassau Street in lower Manhattan at the height of the skyscraper building boom.
In spite of his professional accomplishments, Charles leaned heavily on drink to ease his burdens, whatever they may have been. His mental condition steadily deteriorated, and toward the end of his life, he spent much of his time in rehabilitation centers, according to a descendant. He died in 1908, only three years after his son Frederic married Esther Henshaw.
Frederic's sister Eleanor became a successful music teacher and later moved to a family compound in the Hudson River Valley. Charles jr. studied engineering and established a practice in Albany, New York, later acquiring a farm in Columbia County just outside the upstate village of Valatie. But Frederic, following his father's footsteps, chose to be a Manhattan high flyer. As a successful insurance manager, he kept company with the jet set of his time. Making the rounds of Shelter Island and exotic Hampton resorts in the late 1890s, he found himself in close proximity to the Henshaw family, who vacationed at the same spots and who knew his father, Charles, when he was just a schoolboy in Brooklyn Heights.
Esther, who had been actively attending social events with one of her older brothers in the hopes of landing a mate, finally achieved her objective. She was a beauty in her own right, but more important, perhaps, was her demeanor, which was, to those who knew her, very loving and generous. Her breeding was impeccable, as she was carefully primed, not only by her mother, Cornelia Henshaw, but also by her grandmother by adoption, Sarah Middagh Gracie, a fixture of the Episcopal Church in Brooklyn Heights. Sarah not only made sure that her granddaughters made the social rounds, but held many open teas at the family townhouse in Brooklyn Heights, thus ensuring that the Henshaw daughters would mix with the right crowd in a carefully chaperoned environment.
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To be continued.
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