While serving in Afghanistan, where she was responsible for ensuring the security of hundreds of military personnel, then-Captain Margaret Oglesby took time to address a conference of women whose lives had become freer in the absence of the Taliban regime.
“It was a privilege to do that, to speak to them,” she recalled in a Veterans History Project interview in 2008. “I think God allowed that to happen so they could see that women are capable of leading.”
A leader in positions of authority from Kabul to Western Massachusetts, where she had been a chief probation officer, Ms. Oglesby was awarded the Bronze Star Medal “for exceptionally meritorious service” during her time commanding the 747th Military Police Company in 2003.
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She was 56 when she died Friday in East Longmeadow of complications from early-onset Alzheimer’s disease.
“I thought of her as a bona fide American hero,” said Pamerson Ifill, deputy commissioner of pretrial services in Massachusetts Probation Service. “Her leadership and her honesty and integrity were second to nobody anywhere.”
During 27 years with the state’s Probation Service, Ms. Oglesby rose to be assistant chief probation officer and then chief while serving in different courts.
“Margaret always saw the good in people,” said her longtime friend and former colleague Harriet Beasley, a retired regional supervisor for the Probation Service.
“She had a calm personality and was engaging,” Beasley said. “I would watch her and just marvel at the way she would see through problems and work with people.”
Whether supervising those on probation or serving in the Army National Guard, where she rose to the rank of major before retiring, Ms. Oglesby had a very strong faith, said the Rev. Dr. Marjorie Jones of the Charles Street AME Church in Roxbury.
“She was a devoted Christian and she operated from her heart in everything that she did,” Jones added. “You could depend on Margaret — a strong, yet gentle spirit.”
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In Afghanistan, Ms. Oglesby served during Operation Enduring Freedom, commanding 180 soldiers.
According to her Bronze Star citation, she “was responsible for safeguarding over 300 US personnel, 80 collocated coalition personnel, and over 1,500 Afghani recruits of the fledgling Afghan National Army.”
She provided personal security for visiting dignitaries including Donald Rumsfeld, then US secretary of defense, and she oversaw soldiers who thwarted “several attempted infiltrations” of the Kabul Military Training Center.
That kind of responsibility meant more than eight-hour shifts. “I’m going to say about 18,” she said in the history project interview.
“Being responsible for so many lives was a tremendous — I don’t want to say a burden, but a tremendous challenge,” she added. “Even though I know that I was in charge, you feel like if you make the wrong decision that it could cost someone their life.”
There were other lives to save and influence as well, particularly the women and girls of Afghanistan who would remain after her deployment ended.
“In that culture, you have to understand that it’s very unusual — and probably at that time it never happened, rarely happened — when women told men what to do,” she told the Veterans History Project.
“I often wondered, like, ‘OK, God, what am I doing here?’ " she said, adding she found the answer while speaking with those who lived there.
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“For the young girls to see women doing the jobs we were doing — it kind of flew in the face of the stereotype that they understood about what women and girls can do. So I like to believe that God allowed me to make that new path when I was there.”
The fourth of five siblings, Margaret Elizabeth Jones was born in Springfield in 1963. Her father, Donald Jones, was a laborer, and her mother, Margaret Evelyn Payne, was a homemaker.
Ms. Oglesby graduated from Springfield Technical High School and was 17 when she entered the National Guard, celebrating her 18th birthday during basic training.
“I enlisted because my family couldn’t afford to pay my tuition for college and the National Guard agreed to pay,” she said of the initial reason to sign up.
But over the course of a 28-year career that included serving as president of her officer candidate school graduating class, Ms. Oglesby paired her faith with a sense of duty, even when she was married and the mother of three children.
Beasley once asked if there was a way to avoid being deployed so far from her family.
“She said, ‘I took an oath,’ " Beasley recalled. “She said, ‘This is to protect our nation, our freedoms, our rights.’ "
Ms. Oglesby graduated in 1988 with a bachelor’s degree in psychology from the University of Massachusetts Amherst, where she met Frank E. Oglesby Jr., a fellow student.
“She was a striver. She always looked to better herself,” said Frank, who is the former deputy director of paratransit contract operations for the MBTA, and whose recorded voice is heard on trains and buses announcing stops.
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They married in 1988, and she later received a master’s in business administration from Nichols College in Dudley.
“Margaret was brilliant,” Beasley said. “She was miles ahead of all of us.”
Yet for all her accomplishments, “her calling was to help people in need. She was about helping people,” Frank said.
With the Probation Service, Ms. Oglesby was known for going beyond what was asked. Men and women whose cases had been assigned to other officers often sought her counsel anyway and might be seen crying in her office or asking for advice.
“People talk about empathy as this benchmark, but I think for Margaret, empathy was a minimum standard,” Ifill said. “She was about bringing about real change in people’s lives.”
And in a challenging job, he added, Ms. Oglesby’s laughter and humor lifted colleagues’ spirits.
“Her sense of humor was sharp,” Frank said, “and she had a wry wit as well.”
In addition to her husband, who lives in East Longmeadow, Ms. Oglesby leaves their three children, Frank III of Brooklyn, N.Y., Elizabeth of Washington, D.C., and Nigel of East Longmeadow; a brother, Wendell Jones of Granby; two sisters, Evelyn Howard and Deborah Jones, both of Springfield; and two grandchildren.
A funeral service will be held at noon Friday in Byron Keenan Funeral Home & Cremation Tribute Center in Springfield. Burial with military honors will follow in Massachusetts Veterans Memorial Cemetery in Agawam.
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At times, Ms. Oglesby’s work with the Probation Service and the National Guard intertwined.
“Sometimes if there’s a soldier on probation, I’ll grab them,” she said in the 2008 Veterans History Project interview.
In all parts of her life, Ms. Oglesby “was so forgiving. That to me was one of her outstanding qualities: Her forgiveness of people,” Beasley said. “They just don’t come any better than Margaret Oglesby. I looked up to her as a role model.”
Ms. Oglesby also was aware of her inspirational role within her own family.
“My time away from home was a lifelong lesson to my children to see that freedom isn’t free,” she said in an interview for the 100 Faces of War Experience. “This is a lesson many need to remember because we take a lot for granted in America.”
Bryan Marquard can be reached at bryan.marquard@globe.com.
