Wilson Advance, 28 April 1887.
Henry C. Rountree was a prosperous butcher and grocer.

Wilson Advance, 6 October 1892.
Three years before Edward Cicero Simms was appointed trustee of the Colored Graded School, he was elected constable of Wilson township.

Wilson Advance, 5 November 1880.
[And to answer an earlier question, no, Gray Farmer was not the first African-American elected to office in Wilson County.]

“Prisoners escaping from Wilson Jail. The Re-pop-li-can sheriff and deputy of Wilson eat peanuts while the prisoners escape.”
News & Observer (Raleigh), 21 October 1898.
In the months leading up to the cataclysmic election of 1898, the News & Observer almost daily published political cartoons drawn by Wayne County native Norman Jennett. Former Wilson resident Josephus Daniels had purchased the paper in 1894 and immediately converted it into the organ of the white supremacist Democratic party. In collaboration with Daniels, whom history records as “progressive,” Jennett created a series of panels ridiculing Republican and Populist political figures and featuring stereotypical caricatures of their African-American allies. Riding in the wake of terrorist Red Shirts, the Democrats swept elections, sparking a wave of fury that would ignite the Wilmington Riots and effectively disenfranchise most African-Americans for decades to come.
W.J. “Jack” Cherry, a Populist, was the incumbent sheriff of Wilson County; W.D.P. Sharpe was running against him on the Democratic ticket. (I have not been able to identify the deputy.) Days before the election, the Wilson Advance ran this doggerel:

Wilson Advance, 2 November 1898.
And the jail break?

Wilson Advance, 11 August 1898.

Wilson Advance, 15 October 1880.
“Names of prominent men residing in the several Election Districts of Wilson County NC with explanatory remarks”
5. Israel Barden (col’d). Election district: Wilson. Age: 29. Occupation: Laborer. Where born: North Carolina. Resided in the County: Several months. Ever in U.S. Army or Navy: Never. Remarks: Is quite intelligent. Can read and write a little. Appears to be the most respected col’d man in that section. The colored people prefer him to anyone of their number.
6. Harry Jones (col’d). Election district: Wilson. Age: 52. Occupation: Shoemaker. Where born: Orange Co., N.C. Resided in the County: 2 yrs., 5 mos. Ever in U.S. Army or Navy: Never. Remarks: Cannot read or write. Quite intelligent but colored people seem to lack confidence in him.
7. John Darden (col’d). Election district: Wilson. Age: 35. Occupation: Laborer. Where born: Green Co, N.C. Resided in the County: 5 months. Ever in U.S. Army or Navy: 2 Yrs. in U.S.A. Remarks: Cannot read or write. Not very bright naturally. Won’t do.
North Carolina Freedmen’s Bureau Assistant Commissioner Records 1862-1870, http://www.familysearch.org.