This tale centers around one Chester L. Coltrane, a true gentleman of the Old South affectionately known as Cooter to his closest friends. Cooter was born in 1815, son of a fiery Baptist Minister. Cooter grew up a devout Christian; however he didn’t feel the call as his father had. Cooter became a business man. Cooter made a fortune in the Cotton and Sugar Cane Brokerage trade. Even dabbled a bit in shipping.
As to the peculiarities of Cooters character, they are what made Cooter, Cooter. Cooter didn’t believe in drinking in any form, other than as needed a shot of whiskey and honey to tame a cough. Cooter was as honest as they came.
Cooter believed in the sovereignty of the Union, yet also believed strongly in States rights. Cooter also was adamantly against slavery; a Southern Abolitionist so to speak, if there can be such a thing. Yes Cooter certainly was a mixed bag of principals.
Cooter living in a large port city didn’t get into to much trouble with some of his controversial views. Down plantation way, he’d have been facing a lot of personal criticism, maybe even lynching.
Cooter was a different kind of bird for sure, good or bad, that’s a good question. Don’t know of a good answer, you judge for yourself. I’m not sure that history has concluded anything in that regard.
Anyway, while Cooter was against slavery, he was for the right of the state to determine the yes or no of that question, and not the federal government. Cooter was aghast when the South succeeded from the Union as he didn’t think that was a solution either. Cooter probably was torn with a lot of personal moral conflict as to where his loyalties should lie and what he could or could not as a moral person endorse or support.
So as it is with most people, so it was with Cooter, and that was to act with what understanding and belief you had as an individual. Cooters actions were indeed most unusual and varied.
As the war between the states got going full blast, so did Cooter. As mentioned earlier Cooter was a wealthy man. Cooter hadn’t amassed wealth just for the sake of amassing like some do, but for purpose. Cooter had been very giving towards charity and public works. Cooter was distressed to the extreme over the situation between North and South. He decided to do what he could do, and he didn’t mind how much he spent in the effort.
At first Cooter took a more passive approach by making many overtures and suggestions towards resolving issues and making peace. Many costly communications were sent to both Northern and Southern legislatures, and to President Lincoln and President Davis. It became painfully obvious to Cooter that he was wasting his time.
Cooter then decided to take a different kind of active roll in things. That roll got him to be known by both Confederate and Union forces as a double agent, name unknown, but referred to as “The Fox Who Chases Hounds”
Cooter became calculating as he would infiltrate both sides and then delivery damning information to the other side. Cooters idea was that way quicker collateral damage could be done to the war machines of both sides, thus making the ability to wage war, all but disappear and bring peace sooner and perhaps by losing more lives sooner could save lives in the long run.
Cooters theory had some merit, albeit as one man he really couldn’t impact things all that much. But he sure gave it full effort.
Now since Cooter had committed life and fortune, he wasn’t bashful about where or how he spent it. He had plenty to spend. As a result a lot of slaves were freed during the Civil War. Cooter didn’t know which direction finality would go, so he took a direct role in putting his money where is mouth was regarding the wrongness of slavery.
Now the South was very big on lots of paper work when it came to slave ownership. Slaves were a plantation owners valuable assets and not cheap to come by. Even as much as the cotton growers needed slaves, sufficient money still talked loud.
Cooter was able to talk a lot in that respect. So he went to a couple of plantations and bought them lock stock and barrel at a price no one could resist. Lock stock and barrel of course included the slaves.
Cooter also decided he would look good as a Confederate Colonel, and the uniform would aid in his ploy to free slaves to the safety of the North.
So equipped with all the proper paperwork to show his ownership Cooter would take about four hundred slaves, men women, and children and have them walk behind him on his magnificent stallion wearing his impressive Colonels uniform.
This rather large entourage would then head north, generally to a border where there were not a lot of troop concentrations from either side.
Occasionally, they would run into a Confederate patrol which took a dim view of what looked like a mass slave escape. That is until the impressive faux Colonel Coltrane, produced the almighty paperwork and told a cock and bull story so outrageous that it had to be true.
He would say that these slaves were not only his, but loyal to their beloved master and the South, and as such had been trained to pass for ordinary negro refugees, but were in fact trained saboteurs who would be able to mess up the damn Yankees war effort and never be suspected.
Not only that, Cooter would add, just caring for and feeding them will drain Yankee resources. With that logic being tossed out, the patrols would always let Cooter pass and in many cases actually cheer him.
Now as this entourage got close to Yankee land, Cooter would switch from his Confederate Colonels uniform to a Yankee Colonels uniform. That kept life simple and either way Cooter tried to minimize chances of being taken as a war prisoner by either side.
Cooter made about six or seven such trips before his fortune was gone. Cooter was never caught, but both sides were painfully aware that a person that had been dubbed “The Fox Who Chases Hounds” really existed.
The war ended and Cooter now being broke and penniless was said to have disappeared into the back hill country of Tennessee to eke out a living from the land like many poor white southerners, many who hadn’t even known there was a Civil War.
Some say Cooter is fondly remembered, just not to sure where or by whom. However, the good Lord knows and that’s all that really counts.

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