Pistol dueling editors are part of the history of Kentucky’s first newspaper

Editor’s Note: As Lexington celebrates the 250th anniversary of its founding, the Herald-Leader and kentucky.com each day throughout 2025 will share interesting facts about our hometown. Compiled by Liz Carey, all are notable moments in the city’s history — some funny, some sad, others heartbreaking or celebratory, and some just downright strange.

Disagreements over articles printed in Kentucky’s first newspaper led to two deadly fights, leaving one editor and a civilian dead.

When Lexington was founded 250 years ago, settlers decided they needed a newspaper to keep the 300 people in the area informed. Two of the settlers, John and Fielding Bradford, offered to return east to learn the craft and gather supplies for a press.

When they returned, they started the Kentucke Gazette, the first newspaper west of the Allegheny Mountains.

The paper’s main goal was to provide opinions on state politics and global issues to the American frontier community. Over the years, the name changed to the Kentucky Gazette and the publication grew from two pages to six pages a week. Its goal of providing community members with opinions and news remained.

In 1827, Thomas Roberts Benning came to Lexington to serve as the editor of the Kentucky Gazette, after working as the editor of the Paris Register in Bourbon County.

After Andrew Jackson was elected president, Benning turned his attention to matters at home — farming, education and abolition. Some didn’t take too kindly to the opinions he printed in the paper.

In 1829, Charles Wickliffe, the 21-year-old son of one of the area’s largest slaveholders, Robert Wickliffe, was infuriated by an editorial that painted his father in a bad light.

Wickliffe went to the Gazette office to talk to the writer of the editorial. When he saw Benning, an altercation ensued.

Benning tried to beat Wickliffe off him with a small stick, but Wickliffe pulled out a pistol. Grabbing Benning’s stick and throwing it on the floor, Wickliffe then shot Benning as he was trying to flee through the office’s back door.

“Wickliffe then pulled out another pistol and maintained his stand for a moment in an attitude of menace, in Benning’s office, and finally pulled out a third pistol and stood some time in front of the office threatening to shoot again,” the Gazette wrote about the incident.

“Mr. Benning did not fall when he received the wound but was soon carried from his office to his residence, and had his wound examined … the ball (had) gone through the intestines and lodged in the walls of the belly in the front and to one side. He lived in extreme agony about twenty-four hours and then died,” the Gazette wrote.

Wickliffe was charged with murder, but his defense attorney — one Henry Clay — was able to get him acquitted before a mostly pro-slavery jury sympathetic to the Wickliffe family.

Later that same year, a successor to the editor position was named, Wickliffe’s best friend James George Trotter.

A few months later, Wickliffe again found fault with something written in the paper.

According to an account of the duel by J. Winston Coleman, Wickliffe was upset by “some remarks made in the paper in relation to the death of Benning. This editorial insinuated that young Wickliffe had cowardly murdered the former editor of the Gazette without the latter having a chance to defend himself and hinted strongly at a ‘packed and perjured jury’ and the undue influence of Henry Clay as senior counsel for the accused.”

As a result, Wickliffe challenged Trotter to a duel.

On Oct. 9, 1829, the two men met at the Fayette County and Scott County line. The men fired and both missed their mark, with Trotter’s ball passing through Wickliffe’s pants. Wickliffe immediately demanded a second shot, to which Trotter agreed.

After reloading and taking their positions for a second time, Trotter and Wickliffe fired at each other again. This time, Trotter’s bullet found its mark. Lowering himself to the ground, Wickliffe was examined and found to be mortally wounded. After being rushed to his father’s house at the corner of Jefferson and Second streets, Wickliffe died about three hours later.

An inquiry into the duel found that it had been conducted properly and Trotter returned to his position as editor of the Gazette.

Although many friends of Wickliffe attacked him, Trotter only answered them in the columns of his paper, writing “I abhor dueling. I abhor fighting in every shape and form; but I can say to the whole host of scoundrels who … put themselves behind the breastwork of villainy and rascality, that whenever they are disposed to experiment upon my cowardice, they can be accommodated.”

It wasn’t the last duel for Trotter. According to the Kentucky State Historical Society, “Trotter seems to have been a ready and willing man of war with the pistol, as well as with the quill, when occasion demanded. We hear of him again in 1833, engaging in a personal encounter with George D. Prentice, editor of the Louisville Journal, upon the streets of Louisville.”

The Trotter-Wickliffe duel went down in Kentucky history. Wickliffe, the hot-head who went after newspaper editors was dead. Trotter, after a few more years as the Gazette’s editor, was admitted to and died in an asylum 20 years later.

Have a question or story idea related to Lexington’s 250-year history? Let us know at 250LexKy@gmail.com.