The Winn Family
by Lisa Y. Henderson

Prior to the War Between the States, these families were free, and when the first census was taken in 1790 they were listed as "free persons of color" and sometimes called "free issue."

They intermarried among themselves since they were forbidden by law to intermarry with slaves. Many of them undoubtedly had some Indian blood as well as African blood.

Some of these families owned land, and the Winn family not only owned large tracts of land but they owned some slaves. The Census of 1860 lists these families as Mulattoes.

The first known member of the Winn Family was Adam Winn who originally lived in Duplin County and is believed to have been descended from the Waccamaw Indians.
He moved to Wayne County and bought several tracts of land including land on which the Town of Mount Olive is located.

Adam Winn had five sons: Adam, Gray, Washington, Charles, and Levi.

Adam Winn Jr. married and had five sons: William, Marshall, John, Woodward, and Woodley.

Charles Winn (1817) married America and had the following children: William, Meria, Churchill, Margaret, Levi, Mary, Frances, Lebyet, Wyatt, and Charles.

Gray Winn (1818-1850) married and had the following children: Betsey, Edward, Eliza, Penny, Annie, and Washington Frank.

Levi Winn married twice and had the following children: Henry, David, Pinkney, George, Charles, Mary, Martha, John, Elizabeth, Susan, and Levi.

Washington Winn (born 1820) married first Larky of Sampson County and second, Temperance Brewington and their
children were: Aaron, Levi, Apoly, James, Giles, George, Aubrey, Elizabeth, Lesley, Mary, Della, and Louella. Washington, Charles, and Levi Winn were farmers and also worked as carpenters and blacksmiths.

Read more here:
Wayne County, NC - Heritage Series
http://files.usgwarchives.net/.../history/heritage/winn.txt

He was in for the right thing.
Charles Wynn filed claim #9340 with the Southern Claims Commission. On 1 July 1872, to have his land returned.

He testified: “I am fifty-five years of age, reside in Wayne County, North Carolina …. I resided during the war in Wayne County, North Carolina, on my own land. It contained about 230 acres, 100 of which was under cultivation.”

Tony Roberts, age 40, colored, testified that he lived about a quarter of a mile from Wynn during the war and saw him often. Roberts said Wynn “believed the Union army would succeed, that he thought its cause wasa right, and he was in for the right thing.

William H. Thompson, age 28, colored, swore that he had known Wynn for 24 years and saw him every four months or so during the war. He said Wynn “hoped that the Union army would be successful, put down the rebellion and do away with slavery” and revealed that the Confederate government occasionally pressed Wynn’s wagons and drivers into service to haul its goods.

(Confederate archives revealed two vouchers for hauling arms from Fayetteville to Raleigh, dated in 1862, and signed by others on behalf of Wynn.)

In December 1898, a special attorney rejected the claims of Wynn’s estate:

“We do not care to review the testimony in the case. If the testimony were offered in behalf of a white man under the same circumstances, it would scarcely be sufficient to prove loyalty. But in view of the fact that the claimant was a colored man, his loyalty must be largely presumed from his natural sympathies with those of his own color and those who were fighting, as the colored man believed, in his behalf.”

Historical Documents of Genealogical Interest to Researchers of North Carolina's Free People of Color

https://ncfpc.net/.../14/he-was-in-for-the-right-thing/...