This 1897 photo from Historic New England’s collection shows David Chesnut who worked at the Eustis Estate in Milton, Mass. It was taken when he was in his early twenties while working with the Eustis family’s horses. He was later employed as their chauffeur.
Following his time in Milton, Chesnut worked as chauffer for the Endicott family in nearby Dedham. He purchased property there to build a home and continued to acquire other properties, using them to house extended family and for rental income. By the mid-1920s he owned three houses, becoming one of the only Black landlords in the area.
Chesnut was a jazz enthusiast, and the trumpet was his passion. He played in several marching bands and musical groups, directed local military exercises, and hosted jam sessions in the kitchen of his home. He filled that home with jazz and the marches of John Phillip Sousa, leaving a musical legacy that lasted for generations in his family. Chesnut retired in comfort, having achieved a great deal: a long and stable career, the upward mobility of his family, and a life filled with music.
During Black History Month, we honor David Chesnut’s work, life, and music as we continue to explore his story at the Eustis Estate and beyond.
Eleanor Martinez-Proctor discovered the story of David Chesnut during her year as a research fellow for Historic New England’s Recovering New England’s Voices initiative. Read the article written by her that was published by Atlantic Black Box Project.
Media Contact: Susanna Crampton, [email protected]
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