View All Posts

Sep 08

Dispatches from High Point’s Dark Ages: The Ballad of Joe Jackson, Pt. 3 - by Larry W. Cates

Posted on September 8, 2023 at 11:02 AM by Tamara Vaughan

Originally posted on September 14, 2021

This is part 3 in a three-part series. Click here to read Part 1 and Part 2

In March 1900, Joe Jackson was sentenced to the State Penitentiary for obtaining goods under false pretenses in Cary, North Carolina. Astonishingly, even under these circumstances, he managed to enlist the aid of well-meaning benefactors again:  ladies involved in prison ministry petitioned Governor Aycock to secure clemency for the seasoned desperado, who also seemed adept at charming and inspiring pity. He served far less time than the two years handed down by the court, but it became apparent that while in prison, he and a gang of confederates had managed to set up a counterfeiting operation. A few days after his release, Joe was rearrested and facing trial in a Federal District Court. A minister from High Point traveled to visit him and told him that the local citizens were breathing easier knowing that he was still in jail. Perhaps that statement was a mistake. High Point had not seen the last of the man.

When the federal case came to trial in December 1901, one offender received a ten-year sentence and four others from one to three years each in the Nashville Federal Penitentiary. Joe Jackson, on the other hand—who was the only defendant to represent himself in court and who had actually manufactured the fake currency—was acquitted by the jury. Who says that a non-lawyer representing himself has a fool for a client?

postcard of large brown building with sunset behindJoe Jackson’s short time in the State Penitentiary was productive: he and some fellow inmates set up a counterfeiting operation for which he faced trial in Federal District Court. 

By August 1902, Joe Jackson was back in High Point and up to his same old tricks. Dead drunk, he fell out of his buggy and broke his left leg in front of Sykes Drug Store when the horse shied away from a frightening object. In July 1903, he was shot again by some unknown person while gathering blackberries on the Walton Place. The ball struck just over his right eye and glanced against the forehead, fracturing the skull. He was stunned, but otherwise not gravely injured. Perhaps here was another of Joe’s old partners seeking to settle a score. 

But, Joe’s time was nearly up.

On April 17, 1904, Jackson assailed Police Chief Leighton Gray near Gray’s Meat Market on South Main Street in High Point. He crept up behind Gray, throttled him, and attempted to wrest his pistol away. With tremendous effort, Gray wrenched the hand holding the gun loose and shot twice. One shot hit Joe’s right lung; the second resulted in a fatal injury to the skull. Interestingly, High Pointers were both saddened and relieved by the news. Chief Gray even expressed regret. “I am sorry but I had to do it.” According to the news report, the policeman was “visibly affected over the fact that he had killed a man.” Local ministers Rev. J. M. Hilliard and Eli Reese conducted the obsequies over the slain Jackson, who was only 46 years old.


3 men in black suitsHigh Point’s Chief Gray, center, with Officers Myers and Lovelace, c. 1905. 

It wouldn’t be quite correct to say that the community mourned the outlaw, but there was clearly some sympathy and affection for him in High Point. The reminiscences of Jack Field suggest this sentiment in spades. 

While it is true that Joe Jackson was a dangerous man in general and nurtured wrongs both real and imaginary, … he was at the same time tenderhearted and kind to those he loved and would have laid down his life for one of these. When I was just a little shaver, Joe would take me in his arms and cuddle me like a small girl with a doll. … When Joe was outlawed and captured, the news was spread that he would pass through High Point on a certain train and hundreds gathered to get a glimpse of him, some through curiosity, others to see with their own eyes handcuffed the man they feared. Joe spied me with my father and asked him to hold me up to the car window so he could touch me. My father did and although his hands were encircled with hard steel his touch was as tender as a mother’s.

Field goes on to say that some believed Joe’s attack on Gray was just horseplay—a joke gone bad. Clearly, in the vein of Robin Hood, there was an element of reverence for the nearly invulnerable outlaw Joe Jackson and nostalgia for tales of his life and exploits. Some perhaps identified with a countercultural figure whose enemies were some of the most notable and prosperous men in the town. 

Sadly, Joe’s wife and children paid the heaviest price. One news article depicted them as destitute and desperate, seeking their father who had been apprehended yet again. One little daughter died in the 1890s. Another was entirely blind most of her life. Joe’s wife, Annie Millis Jackson, died of stomach and bowel cancer in 1917. The two surviving children were Clara V. Jackson Scott (1884-1951) and Nellie Jackson Beal (1896-1974). Surely, their lives were haunted by the memory of a notorious and irresponsible father, the repeated childhood traumas and inexplicable absences. Maybe Joe’s soft spot for other people’s children arose out of his guilt for causing so much suffering to his own.


Larry W. Cates is a reference librarian at the Heritage Research Center of the High Point Public Library where he specializes in family and local history. Contact him at 336.883.3637 or


You must log in before leaving your comment