Jameson Jenkins was born in North Carolina sometime around 1810. Presumably upon his arrival in Springfield, Jenkins filed his Certificate of Freedom papers with the Sangamon County Recorder of Deeds, on March 28, 1846. He worked as a drayman, or teamster, who transported goods and on occasion, people. In January 1850, he assisted a small group of runaway slaves North to Bloomington on their way to freedom, as he was also a conductor for the Underground Railroad. Jenkins drove Abraham Lincoln's carriage to the depot where Lincoln would depart for the White House in 1861.