Both John's maternal and paternal grandfathers were founders of Charlottesville and close associates (and neighbors) of Thomas Jefferson. John was born at the Winn house (which still stands) which was built for his grandfather by the mason who did the brick work on Monticello. Unfortunately, his father was apparently not a good farmer and the estate was sold in 1847, the family fortune gone. With the assistance of her father, John's mother opened a boarding house for students at the U. of Virginia but I'm sure he felt the need to leave home and get a job so as to relieve his mother of supporting him, she having three daughters to support.
So, he moved to Richmond and got a job operating a furnace at the Tredegar Iron works. He was working there when the Civil War broke out and he, with two of his cousins, joined the third company, Richmond Howitzers. This unit had been formed as state militia before the war by Jefferson's grandson George Wyeth Randolph. Joining was mostly by invitation and the Howitzers sported many sons of prominent families. I'm certain that John got in because of his cousins - the sons of a prominent Richmond physician - and his family's association with the Jeffersons (and Randolphs). John served until the fall of Richmond. When Richmond fell John was hospitalized in a private home, likely with malaria, but there's nothing in his record as to what happened to him. He definitely was not with the Howitzers when Lee surrendered.
After the war his mother was struggling and he tried his hand at several jobs in Richmond and Charlottesville. Apparently, his mother and sisters were close to destitute by that time. His mother died in 1869 and I think he felt the need to help support his sisters. But he'd also married in 1866 so needed a better job to support his wife and child. He thus became a traveling salesman selling sewing machines. Soon after his mother's death one of his sisters married an attorney who'd stayed at the boarding house and later became a senator in West Virginia. The senator supported his wife's two sisters for the rest of their lives and also helped John financially.
John's first wife died in 1871 in Richmond and, for reasons not known, he moved to Macon, Georgia where he continued to sell sewing machines (probably to the Bibb Manufacturing textile mill) and also had some small acreage where he grew cotton. There he remarried in 1874 and had two additional daughters. His first two daughters remained in Richmond but his son, John Winn Jr., lived in Macon until his death in 1938.
So, he moved to Richmond and got a job operating a furnace at the Tredegar Iron works. He was working there when the Civil War broke out and he, with two of his cousins, joined the third company, Richmond Howitzers. This unit had been formed as state militia before the war by Jefferson's grandson George Wyeth Randolph. Joining was mostly by invitation and the Howitzers sported many sons of prominent families. I'm certain that John got in because of his cousins - the sons of a prominent Richmond physician - and his family's association with the Jeffersons (and Randolphs). John served until the fall of Richmond. When Richmond fell John was hospitalized in a private home, likely with malaria, but there's nothing in his record as to what happened to him. He definitely was not with the Howitzers when Lee surrendered.
After the war his mother was struggling and he tried his hand at several jobs in Richmond and Charlottesville. Apparently, his mother and sisters were close to destitute by that time. His mother died in 1869 and I think he felt the need to help support his sisters. But he'd also married in 1866 so needed a better job to support his wife and child. He thus became a traveling salesman selling sewing machines. Soon after his mother's death one of his sisters married an attorney who'd stayed at the boarding house and later became a senator in West Virginia. The senator supported his wife's two sisters for the rest of their lives and also helped John financially.
John's first wife died in 1871 in Richmond and, for reasons not known, he moved to Macon, Georgia where he continued to sell sewing machines (probably to the Bibb Manufacturing textile mill) and also had some small acreage where he grew cotton. There he remarried in 1874 and had two additional daughters. His first two daughters remained in Richmond but his son, John Winn Jr., lived in Macon until his death in 1938.
Both John's maternal and paternal grandfathers were founders of Charlottesville and close associates (and neighbors) of Thomas Jefferson. John was born at the Winn house (which still stands) which was built for his grandfather by the mason who did the brick work on Monticello. Unfortunately, his father was apparently not a good farmer and the estate was sold in 1847, the family fortune gone. With the assistance of her father, John's mother opened a boarding house for students at the U. of Virginia but I'm sure he felt the need to leave home and get a job so as to relieve his mother of supporting him, she having three daughters to support.
So, he moved to Richmond and got a job operating a furnace at the Tredegar Iron works. He was working there when the Civil War broke out and he, with two of his cousins, joined the third company, Richmond Howitzers. This unit had been formed as state militia before the war by Jefferson's grandson George Wyeth Randolph. Joining was mostly by invitation and the Howitzers sported many sons of prominent families. I'm certain that John got in because of his cousins - the sons of a prominent Richmond physician - and his family's association with the Jeffersons (and Randolphs). John served until the fall of Richmond. When Richmond fell John was hospitalized in a private home, likely with malaria, but there's nothing in his record as to what happened to him. He definitely was not with the Howitzers when Lee surrendered.
After the war his mother was struggling and he tried his hand at several jobs in Richmond and Charlottesville. Apparently, his mother and sisters were close to destitute by that time. His mother died in 1869 and I think he felt the need to help support his sisters. But he'd also married in 1866 so needed a better job to support his wife and child. He thus became a traveling salesman selling sewing machines. Soon after his mother's death one of his sisters married an attorney who'd stayed at the boarding house and later became a senator in West Virginia. The senator supported his wife's two sisters for the rest of their lives and also helped John financially.
John's first wife died in 1871 in Richmond and, for reasons not known, he moved to Macon, Georgia where he continued to sell sewing machines (probably to the Bibb Manufacturing textile mill) and also had some small acreage where he grew cotton. There he remarried in 1874 and had two additional daughters. His first two daughters remained in Richmond but his son, John Winn Jr., lived in Macon until his death in 1938.
So, he moved to Richmond and got a job operating a furnace at the Tredegar Iron works. He was working there when the Civil War broke out and he, with two of his cousins, joined the third company, Richmond Howitzers. This unit had been formed as state militia before the war by Jefferson's grandson George Wyeth Randolph. Joining was mostly by invitation and the Howitzers sported many sons of prominent families. I'm certain that John got in because of his cousins - the sons of a prominent Richmond physician - and his family's association with the Jeffersons (and Randolphs). John served until the fall of Richmond. When Richmond fell John was hospitalized in a private home, likely with malaria, but there's nothing in his record as to what happened to him. He definitely was not with the Howitzers when Lee surrendered.
After the war his mother was struggling and he tried his hand at several jobs in Richmond and Charlottesville. Apparently, his mother and sisters were close to destitute by that time. His mother died in 1869 and I think he felt the need to help support his sisters. But he'd also married in 1866 so needed a better job to support his wife and child. He thus became a traveling salesman selling sewing machines. Soon after his mother's death one of his sisters married an attorney who'd stayed at the boarding house and later became a senator in West Virginia. The senator supported his wife's two sisters for the rest of their lives and also helped John financially.
John's first wife died in 1871 in Richmond and, for reasons not known, he moved to Macon, Georgia where he continued to sell sewing machines (probably to the Bibb Manufacturing textile mill) and also had some small acreage where he grew cotton. There he remarried in 1874 and had two additional daughters. His first two daughters remained in Richmond but his son, John Winn Jr., lived in Macon until his death in 1938.
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