McClain entered the Union Army and the Kentucky Cavalry late in 1861. McClain's unit apparently fought well in the war and Jack must have been equally efficient as a soldier for he was commissioned a year later and promoted to captain in 1864.

Captain Jack McClain

Jack lost his sweetheart, Sally Card, to a fellow Union Soldier, Alderson Keen. The story goes that Sally would not walk under a Union flag here in Burkesville and Keen was going to arrest her. However, he took her home in stead of jail and a courtship sprang up between them followed by marriage leaving McClain broken hearted.

Since McClain was such an excellent soldier during the war, he was commissioned to clear up the area of renegades who had continued to plunder after the war was over. He planned and executed each exploit with the conciseness of an army manual.

During one of these raids, he accidentally killed his best friend. Grief-stricken. He took his own life. Today he is buried in the place where he wished: "On top of the highest hill overlooking Burkesville as that is as near to heaven as I will ever get."

Another legend is that of Joe Coalman, the only white man to duly tried and executed by hanging in Cumberland County. Actually the case should have been tried in Columbia, but because of public resentment against him. Joe was granted a changed of venue to Burkesville. It was almost like jumping from the frying pan into the fire for jury condemned Joe for killing his wife with a shoe knife. He was sentenced to be hung on May 25, 1847.

Many people gathered into Burkesville from many miles around. Some brought baskets of food and picnic at Poor old Joe's expense. Some of the women folk even brought their knitting. Joe was hung on Celina Street south of the Square. The last the Square ever saw of him was when he was driven to the gallows on a two-wheel cart drawn by a yoke of oxen. The cart was  driven by Jack Doherty, a colored man, who received $5.00 for his work. The recording world was born too late to capture the music on this occasion. During the procession to the tree, Tommie Law beat the drum, Even  Shaw played the fife, and even Joe Coleman added to his last tune as he played the violin sitting upon his coffin.

Third story which has been told in more ways than one is that of the first American oil well. Actually the well was not intended for oil but for salt water. The drillers had little success in bringing in a brine well. Suddenly on March 11, 1829, the drillers, Cols. Emerson and Stockton, were amazed to see a huge gush  of thick, black liquid shoot high into the air, run into Renox Creek and then off into the Cumberland River. The mysterious black liquid caught fire. Some people say that he had vowed to strike salt water or hell and, when the oil caught fire, he thought that he really had struck hell. The story goes that he fell on the ground and began to pray. Some of the folks who heard their grandfathers tell the story, say that he ran plumb out of sight, ran clear out of the country, and probably still running today. At any rate he was never seen in Cumberland County again.

The streets of Burkesville have seen more than their share of unforgettable characters and events. One well-known and well-loved citizen who helped this area in legal transactions was Judge B.L. Simpson. Many tales have been spun, retold, fabricated, expounded, stretched, and added to by the many people who hold in high esteem the memories of his invaluable services to his town and county. One of these stories is retold in which is very unusual as the judge always liked to do the telling on someone else.

The story goes that the eminent lawyer was as to defend a fellow called Uncle Link who had been called before the court for some m0onor offense. Uncle Link has become a legend himself over the years.