Military
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Confederate Brig. Gen. John Gregg arrived in Raymond on May 11 with orders from Pemberton to contain the right flank of the Federal army as it advanced north and determine where it was heading. Believing he faced a force only half the size of his own, Gregg decided to attack and devised an ambush in which one regiment would stop the Federal advance at Fourteenmile Creek while two other regiments crossed from the Gallatin Road and pushed the Federals against a bend in the deep creek bed. The plan was sound, but Gregg’s troops did not face an inferior force, and without enough cavalry scouts he did not know how many Union soldiers were coming up the road. Private Sumner A. Cunningham of the 41st Tennessee recalled that Raymond was overrun with soldiers on the morning of the 12 and that amid fun and feasting the long roll sounded as General Gregg moved quietly through town while townspeople watched, unaware of the carnage ahead. Pvt. W.J. Davidson of the 41st Tennessee recalled that Captain Boone’s company was sent out as skirmishers and that after Boone was killed while deploying them, his death briefly darkened the regiment before the excitement of battle took over. Lt. Henry O. Dwight of the 20th Ohio recalled that without warning a great yell from the quiet woods across the brook was followed by a crashing roar of musketry.
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