How the South Could Have Won the War

By David Thomas
The Cleveland Civil War Roundtable
Copyright © 2008, All Rights Reserved

Editor’s note: This article was originally published in The Charger in the spring of 1999.

In the beginning of the Civil War, the Confederacy won many decisive victories. As the war continued, however, the Confederacy weakened and in the end, the Union was the victor. But, could the South have won? There are five events that, had they turned out differently, might have allowed the South to win:

  • First, had Thomas “Stonewall” Jackson not died, he would have been of great importance to the Confederacy in future battles.

  • Second, had cavalry commander J.E.B. Stuart been at Gettysburg, the South might have had a decisive northern victory and won the War.

  • Third, had England come into the War as the Confederacy’s ally, the Northern blockade could have been broken, allowing the South to sell its cotton to England and be re-supplied.

  • Fourth, had the railroad system not fallen into Union hands, the Confederacy would have been able to transport supplies and men to the army.

  • Finally, the Mississippi River was of great importance to the Confederacy. Had Grant not captured it, the Confederacy would have still been able to use it for transportation.

Had history turned differently at these five points, the South might very well have won the war.

The Loss of Jackson

Stonewall Jackson is shot by his own pickets while out scouting the area between Confederate and Union lines at Chancellorsville.

When Jackson died near Guiney’s Station in Virginia on May 10, 1863, Lee was devastated. Jackson had been of great importance to the army and made many indispensable contributions. It was at the First Battle of Manassas on July 21, 1861 that Jackson earned his legendary nickname “Stonewall.” It was Confederate General Barnard Bee who said, “There stands Jackson like a stonewall, rally behind the Virginians!” Jackson had also been vital during 1862 when be made his famous Shenandoah Valley Campaign, which kept the valley in Confederate control. Jackson had also produced a high sense of morale among his troops, which strengthened the army even more.

On May 3, 1863 during the Battle of Chancellorsville, Jackson was wounded by North Carolina infantrymen who mistook him for Union cavalry. Jackson would have his left arm amputated. It looked like Jackson would recover and be back in the saddle. But pneumonia set in and he died a week later on May 10, 1863. It was Lee who stated after Jackson’s arm was amputated, “General, you have lost your left arm, and I have lost my right.” Jackson’s corps would be split in two and given to Ambrose Powell Hill and Richard Stoddart Ewell. Had Jackson not died, he probably would have been at Gettysburg with Lee and produced a Southern victory due to his superior strategies and tactics.

Breaking the Union Blockade

The Union Navy patrolling the Southern coast

When Lee made his first invasion of the North In September 1862, he hoped to achieve a decisive victory. With this victory, the Confederacy hoped to have England enter the war as their ally because of the cotton the South could trade with England. Unfortunately, Lee’s army would lose what would become the bloody Battle of Antietam. The British lost interest in supporting the South, and looked to Egypt to get their cotton. Had the Confederacy won a decisive northern victory and had England allied with them, they would have an overpowering army and navy. More important, key supply lines could have been kept open and the British Navy could have diverted Northern military energy.

J.E.B. Stuart at Gettysburg

J.E.B. Stuart

When Lee made his second invasion of the North in June 1863, he did not have his “eyes” which was J.E.B. Stuart and his renowned cavalry. Stuart was off joy riding in the North and would not return until July 2, 1863. Lee was thrown into battle “blind” with Meade’s Army of the Potomac at a sleepy little crossroads town in Pennsylvania. Since Stuart was absent, Lee had no knowledge of the enemy’s strengths or movement.

The army might have been destroyed had it not been for General James Longstreet’s scout Harrison. He had spotted the Union army while on reconnaissance and reported it to Longstreet who informed Lee. Lee was furious with Stuart’s unnecessary absence when be needed him most. Stuart’s tardiness may have cost Lee the Battle of Gettysburg. Had Stuart been there when Lee needed him, the Confederacy would probably have been aware of the Union positions and crushed them.

The Confederacy’s Railroads

The railroads were of great importance to Lee’s army. They allowed the army to be re-supplied with provisions, ammunition and men. But because the Union army captured the railroads, the Confederacy could not send supplies to the army. Thus it began to starve and decrease in numbers, until it finally had to give up. Never was this more apparent than at Petersburg where railroads at City Point provided Union soldiers a never-ending supply of food, uniforms, ammunition, and arms, while the Confederate troops received no re-supply.

A railroad depot in Tennessee during the Civil War

Losing the Mississippi

When Ulysses S. Grant captured Vicksburg, Mississippi on July 4, 1863, the Union army gained full control of the Mississippi River and split the Confederacy in two. This event weakened the Confederate Army. This allowed the Union to focus their entire efforts on the East.

Union gunboats sailing past the batteries of Vicksburg


It is not hard to picture the following scenario. Jackson survives, and continues to lead a superior force against poorly led Union troops. At Gettysburg, Stuart warns Lee of Union troop movements, allowing Lee to capture the high ground. The British break the Union blockade, allowing the Southern economy to flourish and the troops to be re-supplied. Key railroads remain in Southern hands, allowing for troop movement and provisioning. And the Mississippi River stays in Southern hands, forcing the Union to fight on two fronts.

Had the Confederacy achieved these five goals, they most likely would have won the war. The Confederacy would probably have become their own country and the United States would today consist of thirty-nine and not fifty states.