As Major General Fitz John Porter's assault on Stonewall Jackson's troops struggled under the rain of shot and shell, Major General Irvin McDowell ordered Brigadier General John Reynolds to come to Porter's support. With this, Brigade Commander Colonel Gouverneur Kemble Warren shifted slightly south to occupy the ground at the end of the Union line formerly held by General Reynolds. With only the 5th and 10th New York at his disposal, the 10th would move forward as skirmishers while the 5th remained alone and vigilant. Brigadier General George Sykes, commanding the Division of which Colonel Warren's small Brigade belonged, spoke of his situation.

"The Pennsylvania Reserves, under General J. F. Reynolds, had been posted on my left, south of the Warrenton pike. Just previous to the attack these troops were withdrawn, leaving my left flank entirely uncovered and the Warrenton road open. Colonel Warren, Fifth New York Volunteers, commanding my Third Brigade, seeing the paramount necessity of holding this point, threw himself there with his brigade, the remnants of two regiments, and endeavored to fill the gap created by the removal of Reynolds." [5]

When General Longstreet's massive flank attack moved in their direction, the men of the 5th New York watched in astonishment as their peers from the 10th came streaming past Warren's small command. Colonel Warren found himself unable to order the 5th to fire until the men of the 10th cleared from their front. When they did, General Hood's men aimed a terrible fire towards the obstinate New Yorkers in their path. Colonel Warren attempted to order his men to a better position but found this both a difficult and deadly task. He would say of this part of the battle:

"I then gave the order to face about and march down the hill, so as to bring the enemy all on our front, but in the roar of musketry I could only be heard a short distance. Captain Boyd, near me, repeated the command, but his men only partially obeyed it. They were unwilling to make a backward movement. He was wounded while trying to executive it. Adjutant Sovereign carried the order along the line to Captain Winslow, commanding the regiment, and to the other captains, but was killed in the act. Captain Winslow's horse was shot. Captain Lewis, acting field officer, was killed. Captain Hager was killed. Captains McConnell and Montgomery were down with wounds, and Lieutenants Raymond, Hoffman, Keyser, and Wright were wounded. Both color-bearers were shot down, and all but four of the sergeants were killed or wounded." [5]

Despite the momentum of CSA Major General John Bell Hood's Texas Brigade, the 462 men of the 5th New York did their best to slow the Southerner's crushing advance. When the smoke cleared, 75% of the 5th NY were either killed or wounded. As a testament to their steadfast fidelity, part of the inscription on their regimental monument, pictured above, reads, "In holding this position, the regiment suffered the greatest loss of life sustained by any infantry regiment, in any battle, during the entire Civil War. The casualties were: killed or mortally wounded, 124; wounded, 223. Both color bearers and seven out of eight of the color guard were killed; but the colors were brought with honor, off the field." [C]

In his report General Sykes would add to this description. "The enemy, seeing...that our weak point lay on my left in front of Warren, poured upon his little command, under cover of the forest, a mass of infantry that enveloped--almost destroyed--him" [5]

As Hood's Texans forced back the survivors from the 5th New York, instead of retreating with his comrades, Private James Webb of Company F braved the tremendous musketry fire as he raced north along the ridge to warn the men of nearby Charles Hazlett's Battery of the onrushing danger. Hazlett's artillery, positioned just to the right of the 5th New York's line, made it off the hill without losing their guns. His actions earned the Brooklyn native the United States Medal of Honor. Despite being severely wounded, Private Webb, as his citation reads, "...refused to go to the hospital and participated in the remainder of the campaign." [31]

Alfred R. Waud sketched a somewhat crude representation of Colonel Warren's men being pushed back by Longstreet's advance. Although rough, it clearly shows the confusion and chaos of battle.