Audacious and Dangerous

Waterloo50

Major
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Jul 7, 2015
Location
England
I have been looking through some of my books and searching online for the most Audacious and Dangerous plans ever conceived during the Civil War, I was looking for plans that looked like they could never work but did with great success. I was reading about the more obvious plans that were risky like how Lee and Jackson Split Their Forces and Outflanked the Union Army or the battle of Cedar Creek and the cunningness of Gen John Gordon.

So I have a question, it doesn't matter if its a small skirmish or a large battle as long as the plan was Audacious, brilliant and unbelievable. Can anyone offer other less well know plans that could be considered 'Audacious' I particularly enjoy plans where the odds are stacked in the opposing forces favour.
 
My first offering will be controversial due to the nature of the action. I'd say that Quantrill's raid on Lawrence was both audacious and tremendously risky. It never should have worked, but it did. Even the retreat back to Missouri should have failed, but it didn't. In terms of planning and execution, it was a success. In terms of morality, it will always be condemned by most. Even some of Quantrill's own men would question the morality of what they saw in Lawrence and would leave him because of it.

Secondly, I think Shelby's great raid of October, 1863 was both audacious and risky. It didn't accomplish anything permanent, but it sure upset a bunch of Yankees and tied them up for a period of time. In that regard, I'd say it was a success.
 
Early's 1864 invasion of Maryland.

The plan was to scare the Yankees in Washington and draw off troops from the Petersburg campaign. It worked!
The plan to free the 15,000 Confederate Prisoners was pretty radical and perhaps a little over enthusiastic and it was called off. Was there a plan or was Early reacting to a situation as it unfolded?
 
My first offering will be controversial due to the nature of the action. I'd say that Quantrill's raid on Lawrence was both audacious and tremendously risky. It never should have worked, but it did. Even the retreat back to Missouri should have failed, but it didn't. In terms of planning and execution, it was a success. In terms of morality, it will always be condemned by most. Even some of Quantrill's own men would question the morality of what they saw in Lawrence and would leave him because of it.

Secondly, I think Shelby's great raid of October, 1863 was both audacious and risky. It didn't accomplish anything permanent, but it sure upset a bunch of Yankees and tied them up for a period of time. In that regard, I'd say it was a success.
I half expected to see Quantrill's name mentioned and although the raid on Lawrence is known as a massacre, it was still a dangerous plan none the less.

I need to read up on Shelby's raid, I don't know too much about it.
 
CSS Hunley
You want me to go underwater in that thing?

The CSS Hunley, In my humble opinion that has to rank as one of the most daring raids of the war. A clear plan, audacious, downright dangerous and a success.
I forgot about Naval engagements, there must be loads of audacious and dangerous naval plans.:thumbsup:
 
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The plan to free the 15,000 Confederate Prisoners was pretty radical and perhaps a little over enthusiastic and it was called off. Was there a plan or was Early reacting to a situation as it unfolded?
In a 'small nutshell', we find Early had his own objective, the march on Washington, as a ploy to divert some of Grants troops from around Petersburg to take pressure off Lee. A separate section of Cav was assigned to ride with Early, but to break off, move toward Point Lookout ( breaking rail lines, and any supply depots in their way) in order to free the prisoners there. A ship was also dispatched, carrying arms for the Lookout prisoners. The idea then was to have the freed soldiers move on Washington DC. only 80 miles (as the crow flies) away.
However, the Cav are finally released by Early far to late to accomplish their 2 missions, having only 4 days to move approx. 300 miles, dodging Union Cav and soldiers, while still tearing up railroads. And, the ship was so delayed by bad weather, they finally turned back to port, not even getting close to their objective.
 
In a 'small nutshell', we find Early had his own objective, the march on Washington, as a ploy to divert some of Grants troops from around Petersburg to take pressure off Lee. A separate section of Cav was assigned to ride with Early, but to break off, move toward Point Lookout ( breaking rail lines, and any supply depots in their way) in order to free the prisoners there. A ship was also dispatched, carrying arms for the Lookout prisoners. The idea then was to have the freed soldiers move on Washington DC. only 80 miles (as the crow flies) away.
However, the Cav are finally released by Early far to late to accomplish their 2 missions, having only 4 days to move approx. 300 miles, dodging Union Cav and soldiers, while still tearing up railroads. And, the ship was so delayed by bad weather, they finally turned back to port, not even getting close to their objective.

A great plan then but it went wrong because Early hesitated with his Cavalry, If the Cavalry had been successful but the prisoners were left unarmed I wonder if they would have still marched against Washington.

Thank you for your post, its appreciated.
 
Some daring deeds:

Dahlgren's raid on Richmond to free Union prisoners. Failed.

Confederate sabotage at City Point. August 8, 1864. Success.

US Navy attempt to sail up the James and into the Richmond docks. May 15, 1862. Yankees had iron ships. Just two weeks earlier such an attempt worked at New Orleans. This attempt was stopped at Drewry's Bluff. Failed.

St. Alban's Raid. Failed.

Portland, ME "escape plan". Summary: Lt. Charles Reed, CSN, captured civilian ship Tacony and made it a small raider - Federal ships went after her - Reed captured the fishing boat Archer and transferred to it - burned Tacony in hopes Feds thought that was the end - slipped into Portland, ME - captured Revenue cutter Caleb Cushing - made dash out of harbor - chased by two armed civilian ships - Reed blew up ship and surrendered to mayor - on way to prison in Boston had to be heavily guarded - locals wanted to tear him and crew apart - later exchanged. Failed.

Around Petersburg, Winter, 1865. Summary: Lt. Reed led crew which snuck out of siege - went overland with long boats - freezing, snowy - aim to capture USS Atlanta (former CSS Atlanta) and wreck havoc at City Point - informer dashed plans - Reed & co. saw Yankee cavalry waiting - retraced steps back to Richmond. Failed.

Charleston Harbor, October 5, 1864. Torpedo boat (semi-submergeable) CSS David successfully attacked USS New Ironsides but did not damage her enough to move off station (went for repairs in June, 1864). Failed. Lots of daring stuff went on at Charleston: two naval fleet attacks on the harbor (failed); CSS Chicora and Palmetto State attacks on blockading fleet - destroyed two ships.
 
A great plan then but it went wrong because Early hesitated with his Cavalry, If the Cavalry had been successful but the prisoners were left unarmed I wonder if they would have still marched against Washington.
Unarmed, really doubt that. I think the plan Audacious and Dangerous, likely even dumb. From my readings on Point Lookout, over the last 10 years, those men were in absolutely no condition for that kind of movement. even with full arms.
Not even sure many could carry their arms for any distance. It would have taken months, for many of them, to start to get back into condition. At least, IMHO.
 
Confederate sabotage at City Point. August 8, 1864. Success.
Just had a quick look at this one, Confederate secret service, real James Bond stuff right there and a time bomb, brilliant plan.:thumbsup:

A good description of the explosion.

An hour later, a huge explosion obliterated the barge and most of the wharf, sending debris and the bodies of soldiers flying into the air. 58 people were killed in the blast and another 126 were wounded. Gen. Grant and his aide Horace Porter were near the scene of the explosion. Horace later recalled "…there rained down upon the party a terrific shower of shells, bullets, boards, and fragments of timber. The general was surrounded by splinters and various kinds of ammunition, but fortunately was not touched by any of the missiles." Even from their "safe" vantage point, Maxwell would later report that his local guide Dillard was permanently deafened by the blast.
 
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Unarmed, really doubt that. I think the plan Audacious and Dangerous, likely even dumb. From my readings on Point Lookout, over the last 10 years, those men were in absolutely no condition for that kind of movement. even with full arms.
Not even sure many could carry their arms for any distance. It would have taken months, for many of them, to start to get back into condition. At least, IMHO.
That's something I hadn't even thought about, I guess it depends on the treatment the men received whilst incarcerated and how long they had been held for, so perhaps you are right when you say 'likely even dumb'.
 
"Commando" attack by Lt. William Cushing, USN, on the CSS Albemarle. Albemarle was clearing out the NC coast (area around Plymouth) of Yankees. Had to be stopped. Success.

CSS Arkansas (ironclad) - dashing through, guns blazing, the Union fleet near Vicksburg (July 15, 1862). Successfully docked at Vicksburg amongst cheering crowds. Raised morale; few casualties on both sides; embarrassed Adm Farragut and his officers. Arkansas was damaged almost to the point of uselessness.
 
I'm going to throw in Johnsonville, where Forrest's cavalry captured three Union steamboats and a gunboat, and cost the Federals at least two or three million in damages - Forrest thought it was closer to six million. The battle stopped Thomas' army for a while from preventing Hood's invasion of Tennessee and severely disrupted Union river traffic. This earned Forrest one of his more famous monikers - Sherman dryly wrote, "That devil Forrest was down about Johnsonville making havoc among the gunboats and transports."

The other dangerous and audacious move would be Brice's Crossroads. Forrest was outnumbered three to one and had no doubt he could whip Sturgis. It was the only battle where a commander counted on the weather to make a win!
 

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