Rural residents often viewed lawyers suspiciously if they moved into their neighborhood after the Civil War with the intent of making their fortune. Such was not the case with Benjamin Benson Cahoon. Cahoon hailed from Delaware and was admitted to the bar in the District of Columbia May 27, 1868. Previously he served in the 1st Delaware Volunteer Infantry in the Civil War and participated in the principal battles of the Army of the Potomac.
Cahoon wished to travel west to seek his fortune, and initially located in Jefferson City. Learning there was a better opportunity in Fredericktown, he journeyed there by ox wagon, arriving August 5, 1868, in the town he would make his home.
Cahoon became active in Republican Party politics almost immediately after arriving in Madison County. One day the Republican County Committee asked him to address a political meeting out in the rural precincts, and he accepted the invitation. He made a speech that surprised everyone by its eloquence. That night he sat in his office wondering how on earth he was going to make a go of it; he had just two dollars to his name. From these melancholy reflections he was aroused by the entrance of a sturdy looking old man who introduced himself as Capt. Belkin, proprietor of the Fredericktown flouring mill.
“I heern your speech to-day,” said the old man, “…and I like your style. Reckon you’re pretty hard up, eh? Find it tough work makin’ a livin’, eh?”
Cahoon acknowledged that times were hard and the outlook blue.
“Well,” said the old man, drawing a roll of bills from his pocket, “here’s one hundred dollars for ye and I want you to take it as a loan and pay me when you can, for I know you’re hard up and I like your style and want to see you win!”
Before Cahoon could stammer out his thanks, the old man was gone. From that time, fortune smiled on him. His practice quickly grew, and he made himself known, so that within a few months he became one of the outstanding lawyers of the area. Cahoon impressed local officials, evidenced by his appointment as county attorney in 1869, and by 1870 became circuit attorney, a position he held for two years.
Benson Cahoon purchased vast tracts of land in Madison and adjacent Wayne counties. His land holdings peaked at 55,555 acres. Cahoon promoted the region, hoping to sell this land and its resources. He produced maps of each county, with the front showing the location of his land holdings. The reverse included a detailed discussion of the virtues of both counties, including natural resources and features that might attract entrepreneurs.
Cahoon took a keen interest in local affairs and events. After his death, Dr. G. W. Vinyard, a local doctor, noted that even though Benson Cahoon was a lawyer, he always attended the annual meeting of the Southeast Missouri Medical Association. He even presented papers at some of the events and formed friendships among the members.
Toward the end of his life, Cahoon subdivided his 40-acre home place for town lots, retaining only his residence and the immediate ground. He also presented the city of Fredericktown land for Cahoon Memorial Park, today known as simply Memorial Park.
B. B. Cahoon died November 5, 1923, following several months of ill health. A life of service to the community and region turned out to have left him with little in his estate.