At approximately 4 p.m., Crook — with battle lines formed squarely on the enemy’s left flank — launched his assault. While most Confederates did not know Crook’s whereabouts, evidence suggests that Early had some knowledge of the attack but failed to give it credence. Brigadier General Bryan Grimes noticed some activity on the Confederate left flank around 3 p.m., at least one hour before the flank attack commenced. Concerned about the vulnerability of his position, Grimes summoned Maj. Gen. Stephen D. Ramseur and implored him to reinforce the left end of the line. The units on the extreme Confederate left, dismounted cavalry under Maj. Gen. Lunsford Lomax, a force that many other Rebel commanders rated as sub-par, were the only obstacles that stood in the way of the massive flank attack.

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Ramseur initially shrugged off Grimes’ suggestion, stating that the Union troops Grimes observed was nothing more than a fence row. But when Ramseur peered through his binoculars, he saw Crook’s 16 infantry regiments bearing down on the left. Despite that, Ramseur declined to bolster the left until he first discussed the matter with Early — a tremendous error in judgment on his part. To many, the sight of Crook’s four brigades was plain as day. A Confederate private observed in his diary that he and his comrades could see Crook’s men ‘moving heavy columns of infantry to their right all day. We can see them plainly climbing up the side of North Mountain.’

Between 4 and 4:30 p.m., as the sun began to set behind Little North Mountain, Crook’s two divisions, about 5,500 strong, struck Early’s left, encountering Confederate pickets who put up no resistance and took to their heels, reporting to their comrades in Ramseur’s Division that they had been flanked. Confederate artillery soon opened up, but did ‘little execution,’ Crook later remembered.

As Hayes’ and Thoburn’s divisions rolled down the mountain into a ravine, their orderly lines became jumbled. By ‘the time we arrived at the foot of the mountain and emerged from the woods our lines were completely broken,’ recalled Crook. Speed was everything, and that meant there would be no time to reform. ‘Thence we went, sweeping down their works like a western cyclone, every man for himself, firing whenever he saw a rebel and always yelling and cheering to the extent of his ability,’ recalled the 116th Ohio’s Colonel Thomas F. Wildes.

The Union attackers first ran into Lomax’s dismounted horsemen. Early generally held his cavalry in low regard, and those troopers did little to change his opinion that they had ‘been the cause of all my disasters’ when they could not thwart the Union onslaught.

After the war, some Confederate veterans contended that the panic-stricken cavalrymen did more than Crook’s division to create alarm among the Confederate defenders and break up the left. ‘While standing in position a cavalryman from our left came down our line,’ remembered the 13th Virginia’s Captain S.D. Buck, ‘reporting to each command that we are flanked! This did much for Sheridan and the worthless soldier should have been shot then and there.’ Buck continued his tirade against this nameless horseman, ‘That one cowardly cavalryman is responsible for this disaster.’ While unfair to blame one cavalryman for the disintegration of Early’s line, it is reasonable to surmise that the sound of firing on the left and frantic men from Lomax’s command fleeing their position must have been demoralizing to an army that three days earlier had suffered defeat.

By the time Crook’s men caromed into the Confederate left, Brig. Gen. James B. Ricketts’ division of the VI Corps had linked with Crook’s left. Sheridan’s entire army then pressed Early from the front and left, just as it had done three days earlier at Winchester. Crook had thrown Early’s army into disarray, and Old Jube’s attempts to redeploy troops to bolster his left were counterproductive, as that only weakened the areas that were under pressure by the Union VI and XIX corps.

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