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Oates was a veteran of dozens of major conflicts throughout the Civil War, but it was his command of the 15th Alabama at the Battle of Gettysburg that gained him long-lasting notoriety. On the second day of the battle, Oates and his men charged the Union held position on Little Round Top. Approaching the crest of the hill, the men were thrown back by the first Union volley. After a brief withdrawal to regroup, they repositioned further right and attempted to take the left flank. During the next 90 minutes they made two subsequent charges to no avail. A simultaneous frontal assault and a “right-wheel forward” flanking maneuver by a desperate and depleted 20th Maine halted and captured a good portion of the 15th Alabama.