Margaret Elizabeth “Pooh” (Jones) Oglesby, 56, a retired decorated Major serving with the United States Army National Guard and retired Chief Probation Officer with the Commonwealth of Massachusetts, died late Friday afternoon, August 28, 2020 at the East Longmeadow Skilled Nursing Center. She was born and educated in Springfield, MA a daughter of the late Donald and Evelyn Margaret (Payne) Jones and was a graduate of Springfield Technical High School Class of 1981. She earned her B.S. degree in Psychology from UMASS Amherst Class of 1988 as well as her Master’s degree in Business Administration from Nichol’s College. Simultaneously, Margaret while attending college joined the National Guard and began a career that spanned 28 years, graduating as the President of her class at Officer Candidate School Class of 1993. She served protecting our nation’s airports immediately following the 9/11 attack for nine months, then deployed for nine months in Afghanistan during “Operation Enduring Freedom” at the rank of Captain in 2003. Captain Oglesby was responsible for commanding 154 soldiers as the Commander of the 747th Military Police Company with around the clock operations, in an extremely high threat environment from a former Taliban stronghold, and responsible for the entire security and base defense of the Kabul Military Training Center. Along with this responsibility her duties also included the safekeeping of over 300 US personnel, 80 collected coalition personnel, and 1,500 Afghani recruits of the fledging Afghan National Army. Major Oglesby was responsible for training the first Afghan Military Police and as direct result of her superb rapport and combined operations with the Afghan National Army she was responsible in thwarting several attempted infiltrations which resulted in the perpetrators being turned over to the Afghan authorities. Major Oglesby continued security measures included combat patrols, frequent quick reaction missions, convoy security missions, day and night observation posts, vehicle searches, static security measures, and security and protection details of numerous visiting dignitaries including US Secretary of Defense Donald Rumsfeld. As a direct result of her exceptional performance and dedication she was awarded the Bronze Star on August 18, 2003. Mrs. Oglesby as a civilian also led a long distinguished career with the State of Massachusetts Probation Department for 27 years retiring as the Chief Probation Officer from the Northampton Superior Court on August 24, 2018. Along with her two careers she was actively involved in her religious beliefs, recently joining Mt. Olive Church Ministries of Hartford, and she was instrumental in establishing her own program “New Walk in Life” which helped women who were struggling in many aspects of life. She will be remembered in her missionary work all over the State of Massachusetts, she enjoyed gospel music as well as visiting the elderly providing them with a helping hand and much needed companionship. In essence, Margaret Elizabeth Oglesby will be forever remembered as a faithful and distinguished servant of her God, her Country, and the Commonwealth of Massachusetts. She is survived by her soulmate and best friend and devoted husband of 31 years, Frank E. Oglesby, Jr. of East Longmeadow; her loving children, Frank E. Oglesby, III and his wife Tonia of Brooklyn, NY, Elizabeth F. Oglesby of Washington, DC, and Nigel A. Oglesby of East Longmeadow; her two cherished grandchildren, Bennett A. and Zachary Oglesby; her brother, Wendell M. Jones of Granby, MA; her two sisters, Evelyn R. Howard and Deborah C. Jones both of Springfield; her mother-in-law, Francine Oglesby of Newton; her brother-in-law, Charles M. Oglesby and his wife Gillian Ramjit of Ft. Lauderdale, FL; as well as many nieces, nephews, officers and enlisted personnel in the military, and her family in the probation department. Her funeral will be held on Friday, September 4th at 12 noon at the Byron Keenan Funeral Home & Cremation Tribute Center, 1858 Allen Street in Springfield, followed by burial and military honors at 2:00 PM at the Massachusetts Veterans’ Memorial Cemetery, 1390 Main Street in Agawam. Relatives and friends may call on Thursday from 4-7 PM at the funeral home. As a result of Covid-19 all guest will be required to use social distancing and a mask will be required. Instead of flowers, contributions in Margaret’s name may be directed to the Alzheimer’s Association, 264 Cottage St., Springfield, MA 01104. For more information please visit us at www.byronkeenan.com
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Alzheimer's Disease Association
264 Cottage Street, Springfield MA 01104