[Editor's note: At this time, Octavia Stephens, her daughter Rosa and Octavia's mother lived in Thomasville, Georgia. In late October 1863, they moved from their home in north central Florida to escape possible Union incursions into the Florida interior.]

11 February 1864 letter from Capt Winston Stephens
21 February 1864 letter from Capt Winston Stephens
27 February 1864 letter from Capt Winston Stephens

Captain Winston Stephens didn't die without family close. His cousin Swepston Stephens, also in the 2nd Florida Cavalry, was right beside Winston when the fatal bullet struck him. In October 1866, Swepston Stephens wrote Octavia the following:

Ocala Oct 20, 1866

My Dear Sister Tivie,

.... If it were possible I should never tire of talking with you of dear Winston, that I could be with you how happy I should be to sit and talk of the Dear Departed. You know not the anguish of my heart when he was shot. We were side by side and tho' I was not looking at him when he was shot I heard it and turned and asked him if he was hurt. He turned and looked the reply but could not speak and just at that time my spur was cut off and consequently he fell before I could reach him. I dismounted and took him up and sit him on my house and got up behind him and took him out in that way leaning back against me. That look, the last look was full of love. His lips moved but no word escaped. I see that look now and ever will....

Swepston

University of Florida (UF) Library Archivist Bruce S. Chappell kindly allowed me to sort through the photos of the Stephens family donated to the UF P.K. Younge Library of Florida History. As I looked at them I wondered how Octavia Stephens would feel if she knew that people would grieve with her for her losses over 150 years later. Octavia Stephens never remarried. However, I was pleased to learn Winston and Octavia did leave a family which prospered, and every generation afterwards had a boy named Winston.

Winston John Thomas Stephens was born in 1829. Octavia (Tivie) Louisa Stephens (nee Bryant) was born in 1841. Winston, 12 years older than Octavia, first proposed to her when she was 15, but her parents made her wait until she was 18 before allowing her to marry. They were married on 1 November 1859. They were married less than five years when Winston was killed in a skirmish, outside Jacksonville, on 1 March 1864. Octavia died in 1908, approximately 44 years after her husband.

Octavia Stephens, with Winston (left) and Rosalie (right), ca 1868.

The son Octavia gave birth to in March 1864 was named Winston after his father. He died in 1947 at the age of 83. In the 1880s, after one year at college, he became a teacher in Welaka, Florida, where he married a fellow teacher in 1886. Their son, born in December 1888, was named Winston Bryant Stephens. Winston Stephens later went to dentistry school in Baltimore, Maryland, where he graduated from the Baltimore College of Dental Surgery in 1894 and opened a practice as a dental surgeon in New Bedford, Massachusetts.

Winston and Octavia also had two daughters. Rosalie (called Rosa) was born in 1860, and died in childbirth in 1883. Isabella (called Bell) was born on 14 December 1862 and died, from illness, on 24 January 1863, living only 41 days.

The photographs at the Library of Florida History which I examined covered several generations of the Stephens family. And it seemed every generation had a boy named Winston, and one generation was even represented by a set of twin boys. There wasn't any documentation, except names on the back of the photos, so I don't know if it was Winston Stephens, the great-grandson or the great-great-grandson, who donated the photos to the library. In May 2012, I received an e-mail from Patricia Stephens Haynie, a descendant of Winston and Octavia Stephans, who kindly let me know the materials were donated by her father, the great-grandson of Winston and Octavia.

This journal entry and Swepston's letter are from pages 328-329 of Rose Cottage Chronicles: Civil War Letters of the Bryant-Stephens Families of North Florida edited by Arch Blakey, Ann Lainhart and Winston Bryant Stephens, Jr., published in 1998 [ISBN 0813015502]. Some other information on the Stephens and Brtant familes on this page are also from the book.

We often think of the Civil War as having 622,000 soldiers killed in action, died of wounds or diseases. What we forget is that the casualties numbered in the tens of millions among civilians who suffered heartache. - Thomas R. Fasulo, Webmaster

Winston Stephens' tombstone and short history

Other Letters from Olustee
Battle of Olustee home page
http://battleofolustee.org/