- Massachusetts created the nation's first juvenile correctional system in 1846 when it opened the Massachusetts State Reform School in Westboro for 400 boys.
- In 1969, Department of Youth Services was established as a separate agency under the Executive Office of Health and Human Services. Governor Francis Sargent appointed Jerome Miller as the DYS commissioner in 1969. Miller left the Department to accept a position in Illinois.
- In January 1973, Miller was succeeded by Joseph Leavy. Commissioner Leavy left the Department in January of 1976 and became the President of Communities for People. That year, Governor Michael Dukakis appointed John Calhoun as the DYS Commissioner. Calhoun left the Department in July of 1979 to become the Director of the National Crime Prevention Council.Governor Edward King appointed Edward M. ("Ned") Murphy as Commissioner in October of 1979. Murphy accepted Governor Dukakis' appointment as Commissioner of the Department of Mental Health in 1985. Murphy's replacement was his deputy at DYS, Edward J. ("Ned") Loughran. In July 1993, Loughran resigned to accept a position as Director of the Robert F. Kennedy Memorial.
- In September 1993, Governor William F. Weld appointed William D. O'Leary as the sixth DYS Commissioner. O'Leary had served as an Assistant Commissioner for the Department of Mental Health.
- On January 14, 2002, Acting Governor Jane Swift named Michael Bolden as the new Commissioner of the Department of Youth Services. Bolden replaced Robert P. Gittens who left DYS to accept the position of Massachusetts Secretary of Health and Human Services. Commissioner Bolden resigned from his position and was sworn in as the Associate Justice of the Roxbury Division of the Boston Municipal Court in 2005.
- Jane E. Tewksbury was named DYS Commissioner in April 2005. Commissioner Tewksbury’s first orders of business was to re-establish the DYS Northeast Region. Youth from Essex and Middlesex counties were being served in Dorchester and Worcester, at considerable distances from their families and communities. DYS hired a Northeast Regional Director and administrative staff to oversee operations, re-allocated existing programs and community staff and opened the Northeast Regional office in Middleton, MA.
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