Eileen Weber, a Briarcliff Original - Notebook Vol. 2018-7
By Isabella Fitzgerald, BMSHS Intern
Mrs. Eileen O’Connor Weber was an exceptional woman, but that is something the community already knows. She was a woman whose charisma, generosity, and larger-than-life personality lives in Briarcliff Manor to this day. Eileen was more than just a member of the community. She brought together people from all walks of life and celebrated the beautiful town that she called her own.
Eileen was born on June 12, 1918, or Flag Day, as she reminded all, in Ossining to Mrs. Lillian (nee Macdonald) O’Connor and Daniel J. O’Connor. Mr. O’Connor was the third policeman to be appointed in Briarcliff Manor.
See his picture with the Fire Department’s baseball team ca. 1915. Eileen’s mother was the Postmistress of Briarcliff Manor. She had two brothers, J.D. “Pete” O’Connor and James Hogan O’Connor. Her father unfortunately passed away during the influenza epidemic of 1920.
Eileen grew up in Briarcliff Manor in a big home on Sleepy Hollow Road. She attended the public schools in Briarcliff and was a devout Catholic, frequenting St. Theresa’s church on Pleasantville Road. Her love and devotion to the community came through as she was growing up. Eileen participated in the Girl Scouts, was a member of Briarcliff High School’s student council, and was captain of the varsity girls’ basketball and field hockey teams in addition to being a cheerleader during all four years of high school.
Eileen is second from left in the front row. Maybe this is second grade.
Her love of dancing gained her the nickname ‘Sunshine O’Connor, the jitterbugger from Westchester’. The nickname ‘Sunshine’ is quite fitting!
Eileen and her family were very friendly with the Laws. With graduation and the possibilities of the future on the horizon, Henry Law gave Eileen the opportunity of a lifetime - he offered to sponsor her college education wherever she decided to go. Eileen was very proud of this. After graduating Briarcliff High School in 1936, she went on to study at Edgewood Park School for Girls, located in the former Briarcliff Lodge. At Edgewood Park she was President of the Day Students Association. She graduated with honorable mention in 1938 with a degree in Secretarial Science.
After completing her schooling, Eileen worked at Young & Rubicam, a well-established advertising agency in Manhattan. She worked there for 12 years, making her way to head of human resources. She was an early “Mad Woman”! Her hard work and personality stood out in the male-dominated field at a time when women were not exactly welcome in the business world.
In August 1946, Miss Eileen Margaret O’Connor was married to John "Jack" Frederick Weber, Jr. The couple married at Briar Hills Country Club. Jack had served in the U.S. Marine Corps in the South Pacific Theater for 32 months in WWII. He participated at the Battle of Guadalcanal and was awarded the Navy Cross for heroism against the armed forces of the Japanese Imperial Army in 1944.
In 1952, Eileen decided it was time to take her life in a new direction and she entered the world of real estate. Her outgoing and lively personality would lead her to partner with Betty Tufts, and the pair opened Weber-Tufts Real Estate. Located at 1123 Pleasantville Road in the heart of Briarcliff Manor, the realtors specialized in Briarcliff Manor and Scarborough properties. Eileen must have sold every properly in Briarcliff Manor twice over! She always had stories of the home and its history for her clients, and they instantly felt the pride for the community she held. She also served on the Westchester County Board of Realtors. The business was active until 1994 when it merged with Houlihan-Lawrence, but she remained occupied with the real estate business. In the picture below Eileen- wearing the hat- and her staff or realtors.
Eileen was always involved in the community. She was a founding member of the BMSHS in 1974. She organized many popular BMSHS bus tours - famous two-hour tours of Briarcliff Manor, which had over 100 sites to see and covered 16 miles of land. In every case she stood out from the crowd wearing one of her many hats – as though that were necessary. She bequeathed her Metropolitan-Museum-of-Art-Fashion-Institute-worthy collection of hats to the BMSHS. A modest display can be seen currently at the Center on the lower level of the library.
She volunteered with many groups throughout her life, spreading her joy throughout the Westchester. Some of her endeavors include Phelps Memorial Hospital, the Junior League, The Easter Seal Society of Westchester and the Cystic Fibrosis Foundation. She alsspoke to students at Briarcliff Manor public schools about local history, especially highlighting the history of the indigenous peoples of the area. She spread her love of history to generations younger than she and the children loved her visits. How could you not? She was spreading Briarcliff cheer. Eileen did whatever she possibly could to give to the community that gave her such a wonderful life.
In 1994, she created the Eileen O’Connor Weber Scholarship Fund for a Briarcliff High School graduate, sponsored through the Briarcliff-Manor Scarborough Historical Society. The scholarship is still given yearly to a worthy BHS senior. She was honored in May of 2001 by the Briarcliff Manor Education Foundation for her “innumerable contributions to the community.”
Mrs. Weber eventually retired at the golden age of 87. She spent the last years of her life living the way she always had, joyfully and with her many friends. She was a member of Sleepy Hollow Country Club, where she played bridge and golf. Mayor William J. Vescio declared June 12, 2008 to be Eileen Weber Day in the village of Briarcliff Manor to honor Eileen and her truly phenomenal life. The BMSHS dedicated its new center in the library to Eileen on March 21, 2010. Eileen passed away on December 30, 2012 in Scarborough at the age of 94.
Eileen was a woman beyond her time, and yet, portrayed her time perfectly. Mrs. Weber was the quintessential Briarcliff "it girl" whose active role in the town from her birth to her death leaves a lasting effect on those who remember her and those who are just learning her stories.
She was a living legend; a legacy that will remain in the hearts of the community. She continues to live on in spirit through the Briarcliff-Manor Scarborough Historical Society, as well as in the hearts of those she touched. She was the epicenter of a storm of giving, and reached the entire town with her kindness.
Additional Information on Eileen Weber can be found in the collection at the Briarcliff Manor-Scarborough Historical Society, including the accompanying display which is a selection of Eileen's iconic hats.
Photo credits: BMSHS
Sources:
Mary Cheever - The Changing Landscape: A History of Briarcliff Manor-Scarborough
Briarcliff Manor/Scarborough Historical Society 30th Anniversary Gala booklet
Proclamation of Eileen Weber Day: June 14th, 2008
“The Gazette”, Volume 27, Number 12 - March 25-31, 2010
“The Ossining Citizen Register” - August 9th, 1946, August 20th, 1979 and September 22nd, 1990
Edgewood Park “Chronicle” - December 16th, 1936
“LoHud” obituary - January 2nd, 2013
"Hudson River Tidings" - March, 1954
Scrapbooks, binders, books and folders, in the archives of the Briarcliff Manor-Scarborough Historical Society
Interviews with Mimi Boe, Florence Brennemann, Susan Strawgate Code, and Tina Messina, friends and fellow women in real estate
Isabella Fitzgerald is a Pleasantville native with a love for local history. She is currently a senior at SUNY New Paltz pursuing a bachelor’s degree in Women’s Studies. She was drawn to researching and writing about Eileen because she was fascinated by the way Eileen’s dear friends talked about her and how Eileen lived her life in such a generous, fun, and exciting way.