After the enemy disappeared in his front, Confederate General Robert E. Lee reasoned that McClellan was most likely retreating toward the James River and devised a plan to catch the Army of the Potomac in transit and destroy it.
Gambling that the Federal force would be slowed and spread out while traversing the boggy White Oak Swamp, Lee ordered his divisions of the Army of Northern Virginia, under the field command of Major Generals Benjamin Huger, James Longstreet, and A.P.
Hill, to move up quickly and simultaneously converge upon the Federal troops and supply train where they would likely emerge from the swamp and turn southward toward Malvern Hill, bisecting the front and rear of the column in the vicinity of White Oak Swamp Bridge and Glendale (or Frayser's Farm), respectively, and attempting to execute a double envelopment in the fashion of the Battle of Cannae to destroy McClellan in detail.
The coordinated assault envisioned by Lee failed to materialize due to difficulties encountered by Huger and lackluster efforts made by Major General Thomas J.
"Stonewall" Jackson, but successful attacks made by Longstreet and Hill near the Glendale crossroad penetrated the Union defenses near Willis Church and temporarily breached the line.
Union counterattacks sealed the breach and turned the Confederates back, repulsing their attack upon the line of retreat along the Willis Church/Quaker Road through brutal close-quarters hand-to-hand fighting.
South of Glendale near Malvern Hill, Confederate Major General Theophilus H. Holmes made a feeble attempt to attack the Union left flank at Turkey Bridge but was driven back.
(Glendale was the name of a tiny community at the intersection of the Charles City, New Market/Long Bridge, and Quaker [or Willis Church] Roads, which led over Malvern Hill to the James River.
[10] Leaving the White Oak Swamp and traveling westward on the Long Bridge/New Market Road, the units of the Army of the Potomac made a 90-degree southward turn near the Glendale crossroad toward the James River, and this vulnerable junction was therefore a target of primary defensive importance.
To the south, Major General Theophilus Holmes's inexperienced troops (from his Department of North Carolina, attached to the Army of Northern Virginia) made no progress against Porter at Turkey Bridge and Malvern Hill and were repulsed by artillery fire and by the Federal gunboats Galena and Aroostook on the James.
Major General Thomas Jackson approached slowly from the northeast and spent the entire day north of the White Oak Creek, making only indifferent efforts to cross and attack Franklin's VI Corps in the Battle of White Oak Swamp, then attempting to force the Federals back in a fruitless artillery duel in order that a destroyed bridge could be rebuilt for crossing his army, despite the presence of adequate fords nearby.
Jackson's presence did, however, cause Brigadier General John Sedgwick to move two of his three brigades north from the Charles City Road to reinforce the Federal position at the creek.
Moving slowly after dark on inadequate roads, the brigades of McCall's division became lost and overshot the crossroad, only realizing they had missed their objective sometime in the early morning hours of June 30.
Hill waited for the sounds of Huger's expected opening assault, Longstreet interpreted distant unidentified cannon fire as the signal to begin the coordinated attack.
In their first combat experience, Kemper's brigade conducted a disorderly but enthusiastic assault on the Whitlock Farm, which carried them through Seymour's two 1st New York Parrott rifle batteries on McCall's extreme left flank.
This sudden disturbance caused McCall to deploy his reserve brigade under Simmons from the center to the left to answer the charge, leaving his right flank weakened and vulnerable.
The Confederate brigades met stiff resistance from Meade and Seymour in bitter hand-to-hand combat where men stabbed each other with bayonets and used rifles as clubs.
Jenkins' brigade briefly captured Captain James H. Cooper's six 10-pounder Parrott rifles but were soon repulsed by the supporting infantrymen of the Pennsylvania Reserves regiments.
Artillery had changed front to the left, facing his six 12-pounder Napoleon guns southward to rake Jenkins' regiments with devastating enfilading fire but exposing his own right flank to the west in turn.
Wilcox's regiments were driven off, but soon returned supported by the brigades of Brigadier Generals Roger A. Pryor and Lawrence Branch before Randol's cannoneers could remove their six artillery pieces from the field.
Heavy fighting continued until about 8:30 p.m. Longstreet committed virtually every brigade in the divisions under his command, while on the Union side they had been fed in individually to plug holes in the line as they occurred.
Stephen W. Sears wrote that, when McClellan deserted his army on the Glendale and Malvern Hill battlefields during the Seven Days, "he was guilty of dereliction of duty.
"[30] Lee would have only one more opportunity to intercept McClellan's army before it reached the safety of the river and the end of the Seven Days, at the Battle of Malvern Hill on July 1.