We can look back with 20/20 vision, and now know the South could not have won the Civil War, matched against the North’s superior Navy, technology, population and industry, and infrastructure advantages such as the railroad system.

There were many dramatic battles, and the tide did in fact, ebb and flow. But of the moments where the Confederacy had the best and most pivotal moment in the American Civil War, a new commander in the Confederacy, Robert E. Lee, had the opportunity to deal a Death Blow to the Union. The year was 1862, and it was a moment in history when the stars aligned, so to speak, to offer the South a victory of such magnitude that the Civil War might have ended in its favor.

June 30th of that year had for days, seen the Federal Army of the Potomac in retreat from Richmond toward the James River in a series of actions later named The Seven Days.
Their leader, Union General George McClellan, was under the erroneous assumption, built upon faulty intelligence reports and Confederate misinformation, that he was facing an enemy he estimated at near 200,000 strong, when in fact the Rebel army was no larger than his own, about 90,000.

The Yankees had already fought several heavy actions at Beaver Dam, Gaines’s Mill, and Savage Station. Now the Federals were marching in strung-out columns on the few roads leading south, while the Confederates had the advantage of a series of roads that ran east and west.

That was they key: Potential choke points and flank ambush opportunities, and even the ability to cut the tail of the snake. After attempts to break the Federal line at White Oak Swamp had failed, Confederate commander, General Lee glanced at his map and immediately grasped his good fortune, for the road network below the swamp appeared to offer a once in a lifetime opportunity.

Union General McClellan was heading south, for Harrison’s landing on the James River, and Lee realized he could use the three East/West roads (Charles City, Darby Town, and River Roads) to attack McClellan’s forces; while at the small village of Glendale, the Yankees would bee bottlenecked on only one North/South road. Taking the Yankees in Glendale would cut them in two, affording envelopment and potentially, complete destruction.

Orders were issued immediately, in which Stonewall Jackson was to attack the Union forces rear at White Oak Swamp, thus holding the entire Union rearguard in place. A division under Theophilus Holmes was to cannonade whatever Yankees to reach Malvern Hill (south of Glendale), likewise keeping the Yankees pinned down there.
Meanwhile, Longstreet and Huger’s divisions (a force of over 40,000) would burst through the Federal retreat at Glendale, breaching their long line of march. It was a simple, even brilliant plan. It need only be implemented.

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