When thirty-one-year-old James Armstrong, a valued slave, crossed the Ohio River in a bid for freedom on October 8, 1853, James Rudd, his master, a wealthy Louisville merchant, responded immediately, sending two members of his family, accompanied by a slave catcher from Hamlet Services, in hot pursuit. Armstrong did not get far into Indiana; he was soon caught and returned at a cost of $135 to Rudd in jail fees and other expenses. Almost two months to the day after his first escape, Armstrong was on the run again, this time in the company of Edward, a slave of Christopher Beeler. They were assisted by Moses Bard, a black barber sometimes known as Moses Hurst, and Shadrach Henderson, a black boatman, both residents of New Albany, Indiana, across the river from Louisville. The four headed first to New Albany and then north to Salem, Washington County. For some inexplicable reason, they doubled back to New Albany and took refuge in the basement of the Presbyterian Theological Seminary, where they were arrested by Louisville police on December 18, 1853. Armstrong's recovery cost Rudd $342, the bulk of which – $250 – was payment of an advertised reward. Rudd also confiscated $83 found on Armstrong at the time of his recapture. Worried that Armstrong's actions would affect the disposition of his forty-six other slaves, and clearly peeved by Armstrong's determination to be free, Rudd sold the recalcitrant slave in March 1854 for $1,600, a handsome profit, all things considered.

Armstrong's escapes bring into sharp relief a number of issues associated with the flight of the enslaved from the area, and all along the border between slavery and freedom. Armstrong, it seemed, had taken the initiative, at least in the first instance, to flee his master, to emancipate himself, and when that did not succeed, to seek assistance from those he knew had a reputation for aiding those seeking freedom. The sheer volume of advertisements in local newspapers offering rewards for escaped slaves speaks to the determination of the enslaved to be free, or at least to put some distance between themselves and their masters, as well as the commitment of slaveholders to recover lost property. J. Blaine Hudson has calculated that of all the fugitive slave advertisements he compiled covering the years 1788 to 1861, 42 percent referred to escapes in the years 1850–59.