Jacqueline Bailey, educator and hostess, known as 'The Chief' to friends and family, dies

Jacqueline Bailey was a teacher or principal in both Baltimore and Baltimore County schools for more than 30 years.
Jacqueline Bailey was a teacher or principal in both Baltimore and Baltimore County schools for more than 30 years. (Bailey family)

Jacqueline Bailey, a longtime public school teacher and administrator whose family affectionately nicknamed her “The Chief” because of her take-charge, perfectionist personality, died Feb. 15 of cardiomyopathy at Gilchrest Hospice Center in Towson. She was 97.

Born in 1921 in Baltimore, she was the daughter of Jacob Miller, an operations manager for a major oil company, and Janee Buerriere, a switchboard operator. The family lived in Charles Village, then briefly in the District of Columbia before returning to Baltimore.


After attending public schools in the city, Mrs. Bailey boarded at St. Mary’s Female Seminary-Junior College in Southern Maryland, then a finishing school, now St. Mary’s College of Maryland. She attended Towson State Teachers College, now Towson University, and graduated in 1943 with a bachelor’s degree in education.

The next year she married Perry Ould Bailey, a salesman and later district sales manager for General Mills. The couple lived in Baltimore, where Mrs. Bailey taught in the public schools for the next 10 years. The Baileys were Baltimore Colts fans and original season-ticket holders, attending Sunday home games at Memorial Stadium.


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With the birth of the couple’s son, Stephen, in 1954, Mrs. Bailey took a break from the classroom, returning to teaching in 1965 in the Baltimore County school system. Over the next 22 years, Mrs. Bailey served as a resource teacher, assistant principal and principal. She also received graduate education degrees from Loyola College, now Loyola University Maryland.

Her last job was as principal of Orems Elementary School in eastern Baltimore County. Before retiring in 1987, Mrs. Bailey served on several county and state education committees. She was a member of the Women Educators of Baltimore County and the Maryland Association of Elementary School Principals. She also helped prepare numerous college students for careers in education.

Among her relatives and friends, Mrs. Bailey was known for her strong personality and for being a perfectionist in all endeavors. “She was known as ‘The Chief’ because she always wanted to be in charge, to be the one who organized things and got everything going,” said her daughter-in-law, Joyce Bailey of Ocean Isle Beach, N.C.

Years ago, Jacqueline Bailey received a director’s chair emblazoned with “The Chief,” and she owned a mink coat with that nickname embroidered in the lining.

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In addition to her career in education, she was a first-rate hostess, her daughter-in-law said, especially when it came to the Baileys’ annual Christmas party. “She always rolled out the red carpet for that, and the silver and the crystal,” Joyce Bailey recalled. “She loved candlelight to create a beautiful ambience, and she served the best food.”

The holiday fare in the Bailey household included fillets of beef and hams, from either Graul’s Market or Parker’s, a downtown Towson grocer that closed in 1999. “But the crab dip, she made herself,” said Joyce Bailey. “She wanted everyone to ‘Ooh’ and ‘Aah’ when they came to her Christmas parties, and they did. And that was true even for small gatherings. She wanted it all very fancy.”

Jacqueline Bailey was active in the Three Arts Club of Homeland and served on the board of the Grandview Condominiums in Ocean City. She enjoyed the sun and steamed crabs during summers in Ocean City and, her daughter-in-law added, believed the best Baltimore-area crab cakes could be found at Michael’s in Timonium.

Until two days before her death, Mrs. Bailey enjoyed her favorite daily cocktail, a bourbon Manhattan served on the rocks with two cherries and a dash of cherry juice.

Mrs. Bailey’s husband died in 1999. In addition to her son, she is survived by a grandson, Brendan Bailey of Durham, N.C.

After a funeral Mass at Immaculate Heart of Mary Roman Catholic Church in Towson, Mrs. Bailey was buried in Dulaney Valley Memorial Gardens in Cockeysville.

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