News  The Massachusetts Probation Service announces annual award in honor of Margaret Oglesby, former Hampshire Superior Chief Probation Officer, military leader and hero

The breakfast is held in conjunction with the Veteran’s Day celebration.

“We believe the Margaret E. Oglesby Award in addition to honoring her legacy, reflects the commitment and the service of each and every employee of the MPS, and it is a fitting tribute to her service on contributions to our nation, the citizens of the Commonwealth and to the Massachusetts Probation Service,” said Probation Commissioner Edward J. Dolan. 

Mrs. Oglesby, former Hampshire Superior Court Chief Probation Officer, passed away on August 28 after a long illness. She was awarded a Bronze Star medal for her service in Afghanistan where she was deployed for nine months during “Operation Enduring Freedom.” She served as a US Army Captain and was responsible for commanding 154 soldiers as the Commander of the 747th Military Police Company with around the clock operations. 

She also trained the first Afghan military police company. Prior to her service in Afghanistan, Mrs. Oglesby served the country as a member of the military by protecting the nation’s airports immediately following the 9/11 attacks. She served in the Army National Guard for 28 years. Mrs. Oglesby served as a Captain and Commander of the 747th Military Police Company based in Southbridge. Mrs. Oglesby retired as a Major in 2010. She was recognized by the Springfield City Council and named “Outstanding Massachusetts National Guard Mentor for 2003.” 

Mrs. Oglesby retired from the Massachusetts Probation Service in 2018 after serving as the Chief Probation Officer at Hampshire Superior Court from August 2013 until October 2018. She was an Assistant Chief Probation Officer at Springfield District Court from March 1999 through August 2013. Mrs. Oglesby first joined MPS in 1989 as a Probation Officer at Norfolk Probate & Family Court.