Many formerly enslaved people from Boone County found their way to freedom in Ontario, Canada. This was the final destination for the Underground Railroad, as US Federal Fugitive Slave Law held no sway in Canada and the risk of capture and re-enslavement was greatly reduced. Though the security gave great relief, the reality of learning their way through a new life in a foreign land could be difficult and some fared better than others. News reports favoring the position of the South often described the life of a freedom seeker in Canada as one of starvation and misery; that many regretted leaving their “easier” lives as slaves. 

Formerly enslaved people in Canada.

This widespread narrative helped one freedom seeker profit from a former enslaver. Several letters were published in the Weekly Dispatch and County of Elgin Advertiser in 1859 from freedom seeker George Hamilton and enslaver John Barton, of Florence. Though only one side of the correspondence is shown, the letters reveal the complexities of relationships between enslaver and enslaved and Hamilton’s artful deception. 

The first published note is a reply from Hamilton to Barton filled with flattery and confirmation that he (Hamilton) was better off in Kentucky and wished to return. He explicitly confirmed that he would need twenty-five dollars and passes for himself and another freedom seeker named John Zimmerman to return. In a postscript, Hamilton mentions that he would prefer Canadian currency. 

John Barton took the bait and sent money for the two “miserable” men to leave freedom for the comfort of enslavement in Kentucky, but they did not return immediately as expected. The next letter to Barton, over a month later, was written by a friend of Hamilton, who passed along thanks for the thirty dollars Barton had sent. He went on to explain that Hamilton had been ill, his condition likely worsened by the excitement of receiving his fare home. The money Barton had sent was used to pay the medical fees. Hamilton’s thanks and apologies are conveyed, along with another plea for expenses. 

Two subsequent letters over the following weeks repeated the plea for travel fare home and both were sprinkled with tantalizing clues indicating Hamilton had information about other freedom seekers and the name of the “enticer” who had helped him leave Kentucky. He ended one letter with “Please give my love to Old Kentucky and the same to yourself. Be assured that I’ll come home or die in the attempt.” Neither of those things happened, John Barton was fooled only once and George Hamilton was still in Canada years later. 

By Hillary Delaney, Local History Associate