During Major General Fitz John Porter's assault on Stonewall Jackson's troops, Major General Irvin McDowell ordered Brigadier General John Reynolds to Porter's support. With this, Brigade Commander Colonel Gouverneur Kemble Warren moved to occupy the ground formerly held by General Reynolds with only the 5th and 10th New York. When General Longstreet's massive flank attack moved in their direction, the men of the 10th New York who had been out in front came streaming past Warren's remaining waiting infantry. 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 their crushing advance. When the dust cleared, 75% of the 5th were either killed or wounded. 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]

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 a tremendous fire as he raced north along the ridge to warn Charles Hazlett's Battery of the onrushing danger. Hazlett's battery, located on the hill 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 very rough representation of Colonel Warren's men being pushed back by Longstreet's advance. Although rough, it clearly shows the confusion and chaos of battle.