Hayward Shepherd, a black railroad porter in Harper’s Ferry, was the first man killed in John Brown’s raid, an insurrection intended to free Shepherd’s own race from the grips of slavery. Many Democratic newspapers in both the North and South initially reported that Brown’s men shot Shepherd specifically because he refused to take up arms on the side of the abolitionists. Republican presses instead tended to use passive phrases when describing Shepherd’s death, suggesting that they did not want to report the fact that an anti-slavery group had killed a free black man. These moderate presses remained far less opinionated about John Brown and Hayward Shepherd than the extremist presses on both sides of the slavery debate. Differing portrayals of Shepherd’s in newspapers throughout the country suggests that the details of John Brown’s raid were divided more ideologically than regionally. Rumored statements from unreliable sources likely found their way into the press, causing newspapers to relay untrustworthy information about the raid in a variety of articles. The unreliability of the newspaper sources is evident in articles such as an October 19, 1859 report in the New York Herald which stated that “it is true that the negro Haywood, a porter, was shot, but was not killed, as stated by telegraph.” The fact that the deceased was named and renamed so many times – Hayward, Haywood, Heyward, and even Hayard – is also suggestive of the lack ofreliable communication between sources. The truth behind Shepherd’s death, though, seems to be most in line with the conclusion proposed by historian Tony Horowitz in his book Midnight Rising: John Brown and the Raid that Sparked the Civil War. Horowitz asserts that regardless of who shot Hayward, “the reason was almost certainly skittishness.” While this conclusion is still unflattering to Brown’s cause, it also does not provide evidence for the southern propaganda that Brown and his followers were reckless killers. Although the likely conclusion behind Shepherd’s death is relatively neutral, the extremist newspapers shaped such details of the raid to further their own specific agendas.