One incident in particular marks [James] Montgomery's rise as a border raider to be reckoned with. In December 1858 he led a large expedition of sixty to one hundred armed freesoilers from Linn, Osage, and Bourbon Counties into Fort Scott, long hated as the “bastile of the proslavery party” in southern Kansas. Their goal was the liberation of Benjamin Rice, one of Montgomery's close comrades, who had been imprisoned for deeds committed prior to a general amnesty issued by Governor James W. Denver. Montgomery and other freesoilers believed the amnesty should have absolved Rice of past wrongdoing, and they saw his arrest as an act of had faith. They accordingly rode into Fort Scott at dawn with guns drawn, and during the ensuing firefight proslavery man John Little took a bullet in his forehead as he was wiping dust from a window pane to shoot at the raiders. Montgomery and his men freed Rice and beat a hasty retreat out of town, but not before pilfering some money and other items. Little was “a very fine young man” from a good Southern family according to proslavery Kansans, and his death caused a sensation in their ranks.