Military history is full of blunders. Even the best among history's greatest leaders made mistakes in their careers, often at critical times. Napoleon took too long to invade Russia; the Crusader kingdoms decided to march their army in full armor across a burning desert to attack Saladin on his own ground; President Truman even called Douglas MacArthur a "dumb son-of-a-b****."
During the American Civil War, any ill-timed loss or setback could have been catastrophic for either side. So winning when it mattered was vitally important. Too bad no one told these guys.
The Battle of Fredericksburg
There's no better example of poor execution ruining an excellent plan than the Battle of Fredericksburg. When the Union Army under Ambrose Burnside wanted to invade Virginia across the Rappahannock River, all went exactly as planned... until it came time to actually cross the river. Gen. Henry Halleck, who was an excellent administrator but terrible field commander, didn't get the bridges downriver in time for the Union to keep the initiative. By the time they actually crossed the river, the Confederates were ready for them. But even so, the Federals could have been better—and that's Burnside's fault.
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Burnside wasn't exactly acting with military precision when he ordered his subordinates to attack the rebels with "at least a division" when the original plan called for some 60,000 troops. His underlings, following their orders, threw a thousand men in single waves at the reinforced enemy lines. Outnumbered immensely, the Union Army was easily repelled by the Confederates, and then retreated across the Rappahannock.
The Battle of Shiloh
At Shiloh, the Confederates boldly placed their camp near Sherman's headquarters, achieving complete tactical surprise on the morning of the battle—a fight Sherman had been desperate to avoid. Eventually, the unprepared Union troops were forced into a fight by the approaching enemy army. But the Confederates weren't able to press this advantage because Confederate General Albert Sidney Johnston left P.G.T. Beauregard in command of the army from the rear, and then ran off to lead the fight from the front. Beauregard's coordination led to the whole confederate Army getting mixed up in the fight. Later in the day, Johnston was killed after spending too many lives trying to take a fortified Union position called the "Hornet's Nest"—an unnecessary venture.
The next day, the Confederates were down to half-strength, and the lull in the previous day's fighting had allowed reinforcements to reach the Union Army. Not realizing he was now outnumbered more than two-to-one, Beauregard remained in the battle and was himself surprised by a Union counterattack the next morning. The Confederates were later forced to retreat, having completely lost the initiative.
The Battle of Cold Harbor
Cold Harbor could have won the war for the Union in 1864. Instead, it became a lesson learned. During the Overland Campaign, Grant and the Union Army worked away at Lee and the Army of Northern Virginia for nearly two months with some 120,000 troops, outnumbering Lee two-to-one. The culmination of the campaign was an attack on the Confederate defenses at Cold Harbor, where Grant gambled that Lee's decimated army would be so exhausted it would fall to a Union onslaught. If Grant was right, and the defenses fell, then he could go on to Richmond, and the war was over.
Of course, that's not what happened. What happened is the same thing that happens when any army throws thousands of men at reinforced defenses manned by veteran troops: wholesale slaughter. Grant massed his men in front of the Confederate defenses, allowing the rebels to spray Union troops with canister with ease. Grant lost nearly 10% of his army—more than 12,000 men—and the war dragged on.
The Battle of the Crater
During the Siege of Petersburg, VA, an engagement that lasted nearly a full year, Union engineers dug a mineshaft underneath the Confederate defenses. It was a brilliant plan to destroy the Confederate defenses from below instead of attacking them head-on (Grant had learned a lesson from Cold Harbor). A special division had been drilling and training for the assault on the rebel lines that would begin immediately after the mine was blown up. They would roll up the rebels through the hole created in the defenses, and everyone could go home. The only problem was that that division happened to be an all-black U.S. Colored Troops unit, so at the last minute, Gen. George G. Meade swapped them out with a bunch of untrained rabble and put the world's worst officer in charge of the attack.
The mine blew as planned and created a giant crater on the battlefield. The officer in command, Gen. James Ledlie, didn't brief his men that they would be attacking around a crater and then got drunk during the battle. Instead of going around the crater and attacking, the Union troops ran into it, found it was too deep to get out of and were stuck inside while the rebels killed them.
The Battle of Antietam
While Antietam isn't technically a loss, it should have been a slam dunk for the Union Army. Instead, it was a gross loss of life. They outnumbered the rebels three-to-one, Lee had divided his forces into three different parts to facilitate its movement, oh, and George B. McClellan actually had Lee's entire battle plan the whole time. It was found by two Union soldiers and delivered to the Union commander who waited a whole 18 hours to do anything about it. After squandering his foreknowledge of Lee's plans, McClellan then dithered further, allowing Lee's forces to mass near Sharpsburg, Md.
Once the armies were all set, the battle began, and the slaughter commenced. What should have been an easy rout for the Union turned out to be the bloodiest day in American history up until that point. After barely managing a win, McClellan allowed Lee's army to escape without further harassment. McClellan's lack of aggression was so apparent that President Lincoln fired him for it.
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Featured photo of the Battle of Shiloh: Wikimedia Commons