COPELAND AND KAGI HAD TAKEN THEIR STATION at Hall's Rifle Works a few hours before midnight on Sunday, as part of Brown's initial occupation of Harper's Ferry. Brown later sent Leary to reinforce them, after his other men returned from the hostage-taking mission at Colonel Washington's. Soon, however, the factory came under constant fire, and one more man could not possibly make a difference against the steady assault of the assembled militia. Kagi sent a note to Brown, seeking permission to retreat, but Brown ordered them to hold firm.

The three abolitionists continued fighting as best they could, repelling as many as seven attacks, but their ammunition ran low by midafternoon on Monday, and their position became impossible to defend. As Virginians crashed through the entrance to the factory, Copeland, Leary, and Kagi fled through the back door, where they discovered that the “only means of escape if any” was to cross the Shenandoah River. Copeland and the others “turned and fired one round” before wading into the shallow waters, but they hit no one. Some of the Virginians plunged in after the raiders, while almost fifty others stood on both banks and, as Copeland later put it, “opened a hot fire on us from all sides.”

Kagi was hit after he crossed midstream, taking multiple shots in the head and body. According to Mary Mauzy, a local woman who watched the scene, he briefly rose “above the water,” only to be shot again “like a dog” and then “dragged … out a corpse.”

Leary swam to a rock in the middle of the river, where he was “shot through the body” before he could gain purchase. Unable to move, he was later pulled ashore and carried to a cooper's shop, where he lived in agony for another ten or twelve hours.