Four Generations in Hats: A Brooklyn Story of Resilience

Storyline Genealogy  ·  Family Keepsake
The Kenny Family Legacy

The Hats John Kenny Made

How one Irish immigrant's craftsmanship created a legacy of female resilience that sustained four generations across sixty-nine years of triumph and tragedy.

Brooklyn  ·  1854 — 1957

In the decades following the Great Famine, Brooklyn became a thriving hub for Irish immigrant craftsmen in the textile trades. The neighborhood's proximity to Manhattan's wholesale district, combined with waterfront access for imported materials, created ideal conditions for skilled workers to advance from basic textile work into specialized crafts.

The progression from mat weaving to hat making represented more than occupational advancement — it symbolized the American dream in action. Mat weavers worked with coarse materials, producing utilitarian floor coverings. Hatters, by contrast, were skilled artisans who shaped fine felt and straw into fashion items that signaled social status. The journey from one to the other required years of skill development, access to better materials, and integration into professional networks.

John Kenny's Occupational Journey
From mat weaver to master hatter in Ward 7 Brooklyn
Mat Weaver
1870
Matmaker
1875
Hatter
1880 — 1888

This specific progression — documented across multiple city directories and census records — became the key identifier that distinguished John Kenny from dozens of other Irish immigrants with the same name living in Brooklyn during the same period. But the true significance of his craft would only become apparent in the decades after his death.

69 Years of family prosperity
after John's death
(1888 — 1957)
4 Generations sustained
by one craftsman's
legacy
47 Years Aunt Maime devoted
to raising her sister's children
and grandchildren (1888 — 1935)

The Tragedies That Made the Legacy

Brooklyn  ·  1884 — 1888  ·  Five Deaths in Four Years
1884
Generation 1  ·  The First Tragedy

Margaret Kenny Dies of Tuberculosis

On May 24, 1884, Margaret McKenny Kenny died at age thirty-three of pulmonary consumption at 39 Nostrand Avenue, Brooklyn. She left behind her husband John and three daughters: Elizabeth, age five; Mary Agnes, age one; and infant Margaret Mary, about three months old.

Seven weeks later, on July 12, 1884, baby Margaret Mary died of cholera infantum at 39 Sandford Street. John was now a widower with two surviving daughters. Both grandmothers — Eliza Kenny, John's mother, and Ann Lynch MacKinney, Margaret's mother — helped support the family.

In the 1880s, tuberculosis was the leading cause of death in America, and cholera infantum killed thousands of babies each summer in crowded urban tenements. The Kenny family tragedy was, heartbreakingly, commonplace among Irish immigrants in Brooklyn.

1884 — 1888
Generation 1  ·  The Widower's Struggle

John Kenny Raises His Daughters

For four years, John Kenny continued working as a hatter while raising Elizabeth and Mary Agnes with help from both grandmothers. City directories track his progression from matmaker to hatter during this period — evidence of continued skill development even while managing single parenthood in an era with no support systems for widowed fathers.

Then the losses accelerated. In 1887, his mother Eliza Kenny died. On May 10, 1888, his mother-in-law Ann Lynch MacKinney died at age sixty-six. John had now lost his wife, infant daughter, mother, and mother-in-law within four years.

1888
Generation 1  ·  Complete Orphanhood

John Kenny Dies; His Daughters Left Alone

On November 30, 1888 — just six months after losing his mother-in-law — John Kenny died at approximately age thirty-six. His death certificate listed his occupation as "Hatter," representing the culmination of nearly two decades of skill development from mat weaver to master craftsman.

Elizabeth, age nine, and Mary Agnes, age five, were now completely orphaned. Both parents dead, both grandmothers dead. The only family member left was their aunt, Mary F. "Maime" MacKinney, who herself had just lost her mother six months earlier.

In Four and a Half Years

The Kenny family lost five people: Margaret, baby Margaret, Eliza, Ann, and John. Two little girls faced complete orphanhood with no living parents, no living grandparents, and uncertain futures in an era when orphanages were the typical solution. This is where Aunt Maime's extraordinary devotion begins.

1888 — 1920
The Female Survival Network

Aunt Maime Raises Her Sister's Daughters

Mary F. "Aunt Maime" MacKinney — unmarried and living in Brooklyn — took in her orphaned nieces and raised them for the next thirty-two years. Both girls remained in her household through their childhoods, teenage years, and into adulthood. Elizabeth did not marry until age forty-one in 1920, still living with Aunt Maime at the time of her wedding.

This wasn't charity — it was the Irish immigrant survival strategy that kept families together through impossible circumstances. Aunt Maime's devotion would span forty-seven years, eventually extending to her great-nieces and great-nephews.

The Inheritance, in Photographs

Four Generations  ·  Sixty-Nine Years  ·  One Unbroken Thread
~1895
Generation 2  ·  The Inheritance

Mary Agnes Kenny — The Hatter's Daughter

Photograph  ·  Mary Agnes Kenny, circa 1895
Mary Agnes Kenny at approximately age 12 wearing an elaborate feathered hat with large ostrich plume

Mary Agnes Kenny, circa 1895, Brooklyn. Seven years after her father's death, John Kenny's younger daughter wears an elaborate feathered hat with a large ostrich plume — expensive even by middle-class standards.

A studio photograph captures Mary Agnes Kenny at approximately age twelve, wearing an elaborate feathered hat with large ostrich plume. The quality and style of the hat — expensive even by middle-class standards — suggests either family creation using her father's professional network, or prosperity sufficient to purchase luxury millinery.

Seven years after John Kenny's death, his daughter wears a hat that represents everything he worked toward: skill, status, and beauty. This photograph is visual proof that his craftsmanship created lasting value for his children.

1909
Generation 3  ·  Sustained Prosperity

John Kenny's Granddaughters

Photograph  ·  The Robertson Girls, 1909
Lillian Robertson age 3 left Helen Gladys age 1 in ornate baby carriage and a Robertson cousin right all wearing elaborate feathered hats and white fur accessories in a professional studio photograph

Lillian Robertson (left, age three), Helen Gladys (in ornate carriage, age one), and a Robertson cousin (right). Twenty-one years after John Kenny's death, his granddaughters are photographed in luxury millinery.

A professional studio photograph shows three young girls: Lillian Robertson, age three; her sister Helen Gladys, age one, in an ornate baby carriage; and a Robertson cousin. All three wear expensive hats and clothing. The elaborate feathered hats, white fur accessories, and professional photography session represent significant family investment.

Twenty-one years after John Kenny's death, his granddaughters are photographed in luxury that would have been unimaginable to an Irish mat weaver in the 1870s. The hats they wear symbolize three generations of advancement — from survival to prosperity.

1924
Generation 2 & 3  ·  Crisis Again

Mary Agnes and Joseph Robertson Die

Within two weeks of each other, both Mary Agnes Kenny Robertson and her husband Joseph died, leaving three children: Lillian, age eighteen; Helen, age sixteen; and Joseph, age four. Once again, the female survival network activated.

Lillian, barely an adult, became guardian to her younger siblings. Supporting her were both aunts: Mary F. "Aunt Maime" MacKinney — now in her seventies, the woman who had raised Lillian's mother — and Elizabeth "Aunt Lillian" Corbett, Lillian's mother's sister, age forty-five, a WWI Navy Yeomanette.

The Network Holds

The female resilience network that saved Mary Agnes and Elizabeth in 1888 now saves their children in 1924. Thirty-six years of mutual support and female devotion keeps the family intact through another devastating loss.

~1920s
Generation 3  ·  The Sister

Helen Gladys Robertson

Photograph  ·  Helen Gladys Robertson, 1920s
Helen Gladys Robertson youngest daughter of Mary Agnes Kenny Robertson in stylish 1920s cloche hat with patterned trim and fur collar

Helen Gladys Robertson in a stylish 1920s cloche hat and fur collar — the younger sister of Lillian, orphaned at sixteen when both parents died within two weeks in January 1924.

Helen Gladys Robertson, youngest daughter of Mary Agnes Kenny Robertson and sister to Lillian. Orphaned at age sixteen in 1924 when both parents died within two weeks. Raised alongside her siblings by Aunt Maime and Aunt Lillian Corbett. Helen died in 1942, continuing the family's pattern of tragic early losses but having lived to see her family's prosperity and dignity preserved.

1928
Generation 3  ·  New Beginning

Lillian Marries Miles O'Brien

Photograph  ·  Lillian and Miles O'Brien, circa 1930
Lillian Josephine Robertson in stylish cloche hat and fur-collared coat with new husband Miles O'Brien in quality fedora and suit circa 1930 Brooklyn

Lillian Josephine Robertson and Miles O'Brien, circa 1930. Married January 28, 1928 — Lillian in a stylish cloche hat and fur-collared coat, Miles in a quality fedora and suit.

On January 28, 1928, Lillian Josephine Robertson married Miles O'Brien. A portrait from approximately 1930 shows the couple well-dressed and prosperous: Lillian in a stylish cloche hat and fur-collared coat, Miles in a quality fedora and suit. The professional studio portrait indicates continued economic stability.

Forty years after John Kenny's death, his granddaughter — orphaned at eighteen, raised by elderly aunts, responsible for younger siblings — achieves the stability and prosperity that her grandfather's craftsmanship made possible.

~1940s
Generation 3  ·  Enduring Partnership

A Life Built Together

Photograph  ·  Lillian and Miles O'Brien in their mature years
Lillian and Miles O'Brien in their mature years Lillian wearing wide-brimmed hat and suit Miles in dark suit and tie

Lillian and Miles O'Brien in their mature years — Lillian in her signature stylish hat. The enduring partnership that sustained them through Depression, war, and family losses.

Lillian and Miles O'Brien in their mature years, showing the enduring partnership that sustained them through Depression, war, and family losses. Both impeccably dressed — Lillian in her signature stylish hat. This couple, who married when Lillian was recovering from the trauma of orphanhood, built a life of stability that John Kenny's craftsmanship made possible decades earlier.

1942
Generation 4  ·  The Great-Grandchildren

The O'Brien Family — Hats on Every Generation

Photograph  ·  The O'Brien Family, 1942
Multi-generational O'Brien family photograph on porch 1942 Lillian and Miles with children Helen between parents holding twins Michael and Miles Jr. in laps back row Jeanne with oldest daughter Lillian at right and Barbara center both wearing stylish hats

The O'Brien family, 1942. Lillian and Miles seated in the front row with Helen between them, each parent holding one of the twins — Michael and Miles Jr. — and both little ones in their own stylish hats. In the back row: daughter Jeanne, with ten-year-old Barbara (center) and oldest daughter Lillian (far right), both in stylish hats of their own. Four generations of style, dignity, and resilience.

A family photograph captures multiple generations gathered on a porch: Lillian with her husband Miles in the front row, Helen seated between her parents while each holds one of the twins — Michael and Miles Jr. — both little boys wearing stylish hats of their own. In the back row: daughter Jeanne, and two more stylish hats: ten-year-old Barbara Ann, center, and the oldest daughter, Lillian, far right. All are well-dressed, the home comfortable, the family thriving.

Fifty-four years after John Kenny's death, his great-granddaughter Barbara wears a hat at age ten — the fourth generation to carry forward the legacy of style and dignity that began with a mat weaver in Ward 7 Brooklyn. The tradition continues unbroken from the 1870s to the 1940s, and even the twins in their father's arms are wearing hats.

1957
Generation 3 & 4  ·  The Legacy Complete

The Hat That Transcends Time

Photograph  ·  Barbara's Wedding, 1957
Lillian O'Brien dancing with her husband Miles at daughter Barbara's wedding to Thomas K. Hamall in 1957 wearing sophisticated taupe hat and dress

Lillian and Miles O'Brien at daughter Barbara's wedding to Thomas K. Hamall, 1957. Lillian wears a sophisticated taupe hat — so timeless it would still look stylish sixty-one years later when discovered in 2018.

On her daughter Barbara's wedding day to Thomas K. Hamall, Lillian wore a sophisticated taupe hat that would be considered stylish even sixty-one years later when her granddaughter discovered the photograph in 2018. The timeless elegance of that taupe ensemble — modern, refined, impeccably chosen — captures everything the Kenny family legacy represents.

Sixty-Nine Years

Sixty-nine years after John Kenny died, his granddaughter — orphaned at eighteen, raised by aunts, survivor of Depression and tragedy — stands at her daughter's wedding wearing a hat so stylish it could grace a modern fashion magazine. From mat weaver to master hatter to four generations of women who understood that dignity, beauty, and resilience are inseparable: this is the legacy John Kenny made.

The Female Survival Network

Four Women  ·  Sixty-Six Years  ·  1870 — 1935
Ann Lynch MacKinney
The Matriarch  ·  1822 — 1888

Widowed in 1870 when husband George McKenna died. Mother of Margaret — who married John Kenny — and Mary F. "Maime" MacKinney. Helped care for her orphaned granddaughters after Margaret's death in 1884. Died May 10, 1888, age sixty-six, just six months before John Kenny's death. Her daughter Maime continued her legacy of family devotion.

Mary F. "Aunt Maime" MacKinney
The Foundation  ·  1888 — 1935

Unmarried, no children of her own. Took in orphaned nieces Mary Agnes, age five, and Elizabeth, age nine, in 1888 after their father John Kenny died. Raised both girls for thirty-two years until Elizabeth married at forty-one. When Mary Agnes died in 1924, helped raise her orphaned grandchildren. Devoted forty-seven years of her life to her sister Margaret's descendants. Died April 5, 1935.

Elizabeth "Aunt Lillian" Kenny Corbett
The Bridge  ·  1879 — 1950

Orphaned at age nine, raised by Aunt Maime. WWI Navy Yeoman (Female), Brooklyn Navy Yard, 1918. Married John Corbett at age forty-one; no children. When sister Mary Agnes died in 1924, became surrogate mother to orphaned nieces and nephew. Provided stability and family continuity for twenty-six years until her death in 1950. Beloved aunt to Lillian, Helen, and Joseph.

Lillian Josephine Robertson O'Brien
The Survivor  ·  1905 — 1991

Born in Brooklyn, where her grandfather John Kenny worked. Orphaned at age eighteen when both parents died within two weeks in 1924. Became guardian to sister Helen, sixteen, and brother Joseph, four — supported by Aunt Maime and Aunt Lillian Corbett. Married Miles O'Brien January 28, 1928. Raised her family through the Depression. Carried the family legacy forward to the next generation.

Keeper of the Story

Judith Ann Robertson  ·  Born 1949  ·  Montclair, New Jersey
Judy Robertson as a young girl in Montclair, wearing a fur-trimmed bonnet and coat, seated on a stoop with a small terrier

Judy as a young girl in Montclair — the fur-trimmed bonnet continuing a family tradition of hats on every generation.

Judith Ann Robertson was born January 7, 1949, in Montclair, New Jersey — the only child of Joseph Jay Robertson and Ellen Marie Hansen. She grew up on Valley Road in Montclair, in the house where her mother had been raised from sixth grade onward. She attended Montclair High School, graduating in 1967, and went on to earn her bachelor of arts degree from Montclair State College, majoring in mathematics and joining Delta Alpha Chi sorority.

Judy spent twenty-one years teaching mathematics at Randolph Middle School in Randolph, New Jersey, retiring on July 1, 2011.

Beyond the classroom, Judy has been the essential keeper of the Robertson family history. She and Don made the trip to the New Jersey State Archives in Trenton, to Immaculate Conception Cemetery in Upper Montclair, and to cemeteries across Brooklyn in pursuit of the Robertson and Kenny lines. The letters and telegrams her father sent home from the Navy were preserved among the belongings of Barbara O'Brien Hamall — and found their way to Judy when Mary Hamall Morales shared them with her. She has corresponded across years, correcting records, sharing documents, and building the bridge between the three orphans of January 1924 and the grandchildren of today.

The hats were never just about fashion. They were about dignity, resilience, and the promise that tragedy doesn't have to end your story. From a widow's determination to a craftsman's skill to four generations of women who refused to let their family fall apart — every hat was a declaration: we survived, we thrived, we honored those who came before us.

The Kenny Family Legacy  ·  1854 — 1957

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Are You Connected to the Kenny & McKenny Line?

If you descend from the Brooklyn Kenny family of the Mat Maker (also Kenney, Kinney; County Longford) or the McKenna / McKenny / MacKinney family of Ann Lynch and George McKenna — or from the connected Lynch, Corcoran, Heffernan, or Robertson lines — in Brooklyn, New Jersey, or Ireland, I’d like to compare notes. Documented trees, Brooklyn and Irish records, DNA matches, and old family photographs have all moved this research forward.

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