Missed Opportunities – Four Battles That Might Have Ended the U.S. Civil War Long Before 1865

Could the Civil War have ended one, two or even three years earlier? Historians have long imagined scenarios which might have forced a speedy conclusion to the conflict. (Image source: WikiCommons)

Could the Civil War have ended one, two or even three years earlier? Historians have long imagined scenarios that might have forced a speedy conclusion to the long and bloody conflict. (Image source: WikiCommons)

“Debates about how the bloody four-year conflict might have ended have raged for years.”

By Jim Stempel

WHAT IF THE South had marched on Washington D.C. in 1861 after the First Battle of Bull Run? Suppose General George McClellan had been bolder during the 1862 Peninsula Campaign. Picture General George Meade pursuing and destroying Robert E. Lee’s army once and for all after Gettysburg. Could any of these scenarios have led to an early conclusion to the U.S. Civil War?

Debates about how the bloody four-year conflict might have ended had one commander or another moved with greater haste, boldness, or discernment have raged for years.

In fact, some of the war’s finest scholars, and more than a few ‘armchair historians’ as well, have explored all manner of ‘what if’ scenarios. And playing these sorts of guessing games carries risks – anyone bold enough to hypothesize is often greeted with scorn, derision and ridicule. After all, Civil War buffs are a passionate breed!

Nevertheless – and grasping full well the firestorm such speculation often ignites among aficionados of the period – I will offer up a few speculations of my own, stipulating as I do, that they are my own humble opinions, and nothing more.

Could the Union army have been destroyed following the Battle of Cold Harbor? Lee believed so. (Image source: WikiCommons)

Both Lee and Grant were convinced that victory was within reach in 1864. (Image source: WikiCommons)

The Overland Campaign

The most hotly debated question has always been: were there times when the South might actually have won the war? I think the answer to that question is a qualified yes, so let’s begin here.

In my recent novel Windmill Point (published by Penmore Press) I have tried to bring to life through historical fiction the two-week period in the late spring of 1864 when both North and South had reason to believe victory was within their grasp.

At the time, General Ulysses S. Grant had confidence that Lee was weak and that one more hard push would crush his opponent’s army. Lee believed that another bloody disaster like the one his troops had inflicted at Cold Harbor might well cause Northern political will to dissolve. But the Rebel leader also realized that if the Union army gained the James River it could lay siege to Richmond. With the enormous advantage the North maintained in men, material, manufacturing, etc., a siege of the Southern capital would be fatal to the Confederacy.

The fighting and jockeying for position went on for weeks until Grant finally executed one of the most well conceived tactical and logistical maneuvers of the war – he slipped away from Lee, crossed the James, and marched on Petersburg unopposed. In doing so, he erased Lee’s slim chance for victory.

McClelland's army was vulnerable to a potentially war-ending knock out blow in 1862. (Image source: WikiCommons)

Was McClelland’s army vulnerable to a war-ending knock out blow in 1862? (Image source: WikiCommons)


Yet a far better occasion for Southern victory materialized earlier in the war. In my book The Battle of Glendale; The Day the South Nearly Won the Civil War, I presented what I thought was the best opportunity the South had to achieve a victory.

It was spring, 1862 and McClellan was beating a hasty retreat from the gates of Richmond in a string of rearguard actions that would later come to be known as The Seven Days. McClellan, mentally overwhelmed by events, was convinced he was being pursued by a foe that outnumbered him two-to-one. In fact, the opposing forces were nearly equal. The Federal army was strung-out on miles of narrow country roads making for the James River; the Confederates pursued in three separate columns. One prong, under Thomas “Stonewall” Jackson, dogged the Federal rearguard. Another under Theophilus Holmes, rushed to head off the Yankee retreat at Malvern Hill just north of the James. A third detachment, the “battering ram” of James Longstreet, moved to overwhelm the enemy’s hastily assembled defensive line just west of a small country village known as Glendale. If it could strike in force, the Union army would surely be cut in two.

McClellan, overwrought and delusional, had abandoned his army for the safety of the gunboat Galena on the James without appointing a second in command. The leaderless Army of the Potomac had never been more vulnerable.

Astonishingly, Lee’s brilliantly conceived plan would go horribly wrong, bungled in an inexplicable succession of command errors and miscues that went off repeatedly and spectacularly like a string of errant fireworks. Yet despite the myriad of setbacks, a single brigade of South Carolinians did momentarily break the Yankee center, thus cutting the Federal army in two. But with no units rushing in to widen the gap, the fleeting chance to annihilate the Union army was lost. Never again would the South be presented with such an opportunity. As Douglas Southall Freeman wrote of Glendale, “It was the bitterest disappointment Lee had ever sustained, and one that he could not conceal.”

Union guns were rushed to the northern outskirts of Washington D.C. in 1864, as Jubal Early moved to take the Yankee capital from the rear. (Image source: WikiCommons)

Union guns were rushed to the northern outskirts of Washington D.C. in 1864, as Jubal Early moved to take the Yankee capital from the rear. (Image source: WikiCommons)

Early Too Late to Take D.C.

The last Confederate opportunity that I think bears examination is Jubal Early’s 1864 raid on Washington, which followed close on the heels of the Cold Harbor. Early’s Division had worked its way up the Shenandoah Valley, crossed over into Maryland and was marching virtually unopposed on Washington. Brushing aside a valiant effort to stop him along the Monocacy River near Frederick, Early closed on the outer defenses of the Yankee capital, finding them almost undefended. But “Old Jube” was no Stonewall. Southern scouts found Washington’s earthworks vacant in places (Grant had virtually stripped the garrison for his spring campaign), yet Early still balked.

The chance to enter the city, put government buildings to the torch and even raid the treasury was tantalizingly close, but Early turned away. Of course, his small army – perhaps no more than 9,000 men – could never have held Washington. But the political damage it could have inflicted upon the Lincoln Administration would have been incalculable, particularly in an election year. And it was the White House, not Meade or Grant, or even the people of the North that was the real force behind the Union war effort. But Early dallied, and by the following morning Grant’s reinforcements had arrived. Suddenly outnumbered in hostile territory, the Southern commander had little option but to race for home.

Might the Civil War have ended at Antietam's "Bloody Lane"? (Image source: National Parks Service)

The Confederacy might have been crushed decisively at Antietam’s “Bloody Lane” had the Union army moved more swiftly. They did not. (Image source: National Parks Service)

Dashed Hopes in the North

As for missed Union opportunities to end the war early, I believe there was really only one.

Many argue that Meade lost such a chance by not aggressively pursuing Lee’s army after defeat at Gettysburg, but I think that analysis fails to adequately take into account the condition of the Federal army at the time.

The Army of the Potomac had been mauled in the three-day battle, and its command structure was grievously compromised. Meade had lost four corps commanders (Reynolds, Hancock, Sickles, and Gibbon) in the fighting, along with numerous division and brigade commanders. He himself had been awake for nearly 72 hours straight and his army was simply in no condition to mount an aggressive pursuit on July 3rd or 4th, no matter what opportunities presented themselves.

I think the only real opening to end the war in a single blow for the North was lost in 1862 during the late morning hours at Antietam. It was then that Union forces overwhelmed and then crushed the Confederate center at what later would be called “the Bloody Lane.” As Federal commanders on the field frantically begged for reinforcements to press the attack, George McClellan, watching the action from afar at the Pry House, demurred.

The Confederate battle line had been blown wide open, no Southern reinforcements were rushing forward to fill the void. That’s because there were none. Yet McClellan, utterly incapable of seizing the moment, refused to budge. Decisive action and boldness were simply not a part of his DNA, so sadly, the war would rage on for almost three more years.

51lAAtHxOQL._SX348_BO1,204,203,200_Delusion, confusion, fear, ignorance, hubris, exhaustion – upon these familiar human frailties do the spokes of history often turn, and turn they did during the American Civil War.

(Originally published in MilitaryHistoryNow.com on Apr 22, 2016)

Jim Stempel is the author of the new Civil War novel Windmill Point. He has published books on military nonfiction, historical fiction, spirituality and satire. His articles have appeared in numerous journals including North & South, Concepts In Human Development, and The New Times. He is a graduate of The Citadel, Charleston, South Carolina, and lives with his wife and family in Western Maryland.

5 comments for “Missed Opportunities – Four Battles That Might Have Ended the U.S. Civil War Long Before 1865

  1. Veritas
    22 April, 2016 at 1:38 am

    I believe you may have missed the failure of Bragg to follow up and destroy the union army after he had crused it in 1863 and allowed it to retreat to Chatanooga. Had he persued it he would have destroyed this army.

    Lee should have also ordered his army to carry out guerilla warfare after tye St. Petersburg seige had started. He could not have won but then neither could the North and eventually the North would have come to terms rather than wage an endless unpopular war.

    • 22 April, 2016 at 2:11 pm

      Good points! But I think that even had Bragg followed-up — which was not in his nature to do — that success would not have ended the war. The Potomac Army was still in the field, and that was ultimately what mattered. As to guerrilla warfare, you have a point. Many Confederate officers wanted to fight that way. Porter Alexander has a fascinating tale regarding that in his personal memoirs, titled Fighting for the Confederacy. He was with Lee at the surrender and suggested a form of guerrilla warfare, but Lee would not hear of it. Lee believed — accurately, no doubt — that that sort of response would doom the South for generations, an with that he steered the South toward a peaceful future — something he gets little credit for. But excellent points. Thanks. Jim Stempel

    • JimS
      9 June, 2016 at 11:39 am

      In my opinion, Bragg actually made the right call in not listening to Forest in this case. Forest was wrong in his report. The Army of the Cumberland had retreated but they were not fleeing, they were busy making field fortifications and getting ready for another fight. Further, at key roadblocks the advance elements of any pursuit force would have been going up against tough units in prepared positions armed with repeaters. There would have been no element of surprise. I don’t think it would have been easy to destroy the Army of the Cumberland and it may have turned into a battle similar to Franklin only earlier and further south. Keep in mind the Army of Tennessee was also mauled pretty bad at Chickamauga as well.

      The real opportunity missed to destroy the Army of the Cumberland was before the Battle of Chickamauga but Wheeler (general incompetence) and Forrest (inexperience at commanding that many troops) made mistakes that let Rosecrans get his forces back together in the brink of time. Failure in the Saddle by a Dave Powell (while a little harsh on Forrest) is an excellent read regarding both before and after the Battle of Chickamauga.

      Well if Lee had opted for guerrilla warfare, the south would have really howled. I am glad that Lee didn’t go that route as it would have simply been more deaths for a lost cause and they still would have been defeated. You would have a harsher peace imposed on the south and as Johnson (who was already wanting to make a harsher peace than Lincoln) was in office for the next 4 years, the south isn’t going to get a favorable peace when the U.S. Armies in the field have successfully defeated their armies and driven them into guerrilla style war. Also going guerrilla style probably would have eroded any sense of mercy in Grant relatively quickly. Though the south would have been so completely crushed that there is likely no Jim Crow era, no segregation, that would have been a plus.

      I am curious why you think the North couldn’t have won. Even guerrilla fighters need ammunition, arms, and food to fight. Who is going to provide that? Further, 1864-1865 showed the Union forces had no qualms about burning crops. Also by 1864-1865 I think you miss just what a potent force the Union cavalry had become. Look at what they did in Alabama and Mississippi.

  2. Abraham Blondeau
    22 April, 2016 at 2:58 pm

    Thanks for the article! It is always interesting to dwell in the counter factual for a while. Churchill wrote a Civil War counter factual wittingly titled “If the South Had Lost the Battle of Gettysburg.”

    I do not think the South could achieve a military victory over the North, but they could have fought to recognition at least. Just as in WW1, where the last German offensive in late 1917, early 1918, almost broke the Allies back, I think Lee’s only chance was in 1864 when the North was war weary and President Lincoln’s political power showed signs of weakness. If Early had hit Washington, if Bragg or Johnson had been able to stop Sherman’s capture of Atlanta, and if Lee could have held the James River, it is possible there could have been an armistice or political recognition.

    However, the North should have crushed the Southern armies long before 1864 if they had been led properly. It was the beginning of the age of attrition, and some differences cannot be made up by maneuver and courage alone.

    In the end, the war ended the way it should have with a Union victory. Lee had a greater reputation in defeat than if he had waged guerrilla war, and the modern American command system was established. America had a bigger destiny to fulfill, and could only do so united.

  3. Douglas Masucci
    12 June, 2016 at 8:00 am

    Thank you for the article.
    I just finished Windmill Point, a great read! I never realized that Grant was actually forced into the battle at Cold Habor.
    One of my wife’s great,great,great uncles (I may have miscounted) was one of the few confederates lost in the initial battle there

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