What were the top 5 missed opportunities of the American Civil War?

I might not be following. How exactly does Johnston relieve the siege of Vicksburg by standing and waiting for Grant to attack him?
Sorry for any confusion, but I am referring to the battle of Jackson, on May 14, 1863. The stubborn fight put up by Gregg two days prior at the battle of Raymond convinced Grant he needed to deal with Johnston and destroy Jackson before turning his attention back to Pemberton and his Vicksburg army. Had Johnston defended Jackson and held the rail center, Confederate reinforcements would have been able to arrive, disembark and quickly reinforce Johnston's growing "Army of Relief." By abandoning Jackson, he made it impossible to quickly gather his reinforcements into a threatening strike force to the east of Grant, allowing Grant's forces to then turn and deal with Pemberton at Champion Hill on May 16.
 
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Sorry for any confusion, but I am referring to the battle of Jackson, on May 14, 1863. The stubborn fight put up by Gregg two days prior at the battle of Raymond convinced Grant he needed to deal with Johnston and destroy Jackson before turning his attention back to Pemberton and his Vicksburg army. Had Johnston defended Jackson and held the rail center, Confederate reinforcements would have been able to arrive, disembark and quickly reinforce Johnston's growing "Army of Relief."
Ah, I see the source of the confusion.

The ~20,000 figure I gave for Johnston's force was after all the relief troops had arrived (i.e. the high point of Confederate forces in theatre, just before Vicksburg surrendered). On May 14 Johnston's force at Jackson was only about 7,500 strong, and Grant's force that had already crossed the river outnumbered him about 7:1 - if Johnston stands and fights he'll be crushed.
 
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I think Grant and Sherman were looking for a chance to get east of Johnston while he was in Jackson. They would hold the bridges over the Pearl River, and push Johnston westward, so that his force was trapped in Vicksburg, too.
Johnston's force was small and not experienced. And when Loring was told to fight, he saw there was another entire corp in his front, of full roster divisions.
The Confederates had only hazy ideas of the dimensions of Grant's operation, until they saw the US troops.
 
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On May 14 Johnston's force at Jackson was only about 7,500 strong, and Grant's force that had already crossed the river outnumbered him about 7:1 - if Johnston stands and fights he'll be crushed.
That was May 14th. By May 16th Ector's and McNair's veterans would be expected to arrive giving Johnston an additional 3,000 or so troops to the 7,500 already concentrated there. Johnston had substantial artillery available to stiffen his defensive position. With Pemberton threatening to maneuver his Vicksburg troops against Grant's rear during this same time period, I don't believe Grant would have committed his total force (7:1 or whatever the odds) against the 7500 Confederates then holding Jackson. He might have, in which case your scenario would be correct (Johnston's force would have been crushed), but given the precarious position of Grant's army and the state of the intelligence available to both sides (both sides were woefully short of cavalry), would he take that gamble? I just can't see it painted quite as "black and white" as yourself. I think had Johnston been just a bit more of a gambler, he had a chance to hold Jackson against any initial assaults Grant might have thrown at him and perhaps turned the tide of the whole Vicksburg campaign at that point. Not very good odds still...but a distinct possibility at least.
 
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That was May 14th. By May 16th Ector's and McNair's veterans would be expected to arrive giving Johnston an additional 3,000 or so troops to the 7,500 already concentrated there. Johnston had substantial artillery available to stiffen his defensive position. With Pemberton threatening to maneuver his Vicksburg troops against Grant's rear during this same time period, I don't believe Grant would have committed his total force (7:1 or whatever the odds) against the 7500 Confederates then holding Jackson. He might have, in which case your scenario would be correct (Johnston's force would have been crushed), but given the precarious position of Grant's army and the state of the intelligence available to both sides (both sides were woefully short of cavalry), would he take that gamble? I just can't see it painted quite as "black and white" as yourself.
What kind of odds do you require to overmatch someone enough to defeat them easily? Let's say for the moment it requires a 3:1 advantage.

In that case, Grant can leave about 15,000 troops PFD to hold back Pemberton's Vicksburg troops (who were about 30,000) and Pemberton can't gain that amount of overmatch against Grant.

Ector and McNair didn't reach Johnston historically until the 26th, but let's say they'd arrive by the 16th. What would the situation look like on the 14th?
Well, to answer that we need to look at the divisions Grant sent to attack Jackson - pretty much the 15th and 17th Corps, with the 13th Corps acting as the covering force (at Raymond).

The force PFD in the part of the 13th Corps that crossed the river was about 17,700 PFD. (That's everything except the parts that fought at the Battle of Helena.)

The other forces that crossed the river were:
7th division of the 17th Corps: 6,500 PFD
HQ + 3rd division, 17th Corps: 6,600 PFD
Main Body 15th Corps 11,100 PFD
2nd Division 15th Corps 5,900 PFD. (Crossed 11th May.)

The 3rd Division 17th Corps (6,500 PFD) crossed the river on 13th May and would be available to join the covering force by the time Pemberton got there; the 2nd Division 15th Corps might have been in either force (attack on Jackson or covering force)

This puts the division of Grant's forces as of the 14th of May as:

Certainly attacking Jackson 24,200 PFD
Certainly in the covering force 17,700 PFD
About to join covering force 6,500 PFD
In covering force or attack force 5,900 PFD

So on the 14th (with fighting beginning around 10AM on that day, as historically) Johnston could have 7,500 in Jackson and be attacked by 24,200 PFD - more than 3:1 odds. If he's able to hold out against that for two days for Ector and McNair to arrive, then 13th Corps alone could hold out against Pemberton for two days even if Pemberton had more than 50,000 troops - and whichever one 2nd Div 15th Corps was in makes things worse.

This is just based on the troops Grant historically committed to the attack against Jackson, no matter how poor his intel was. And historically Grant was kind of gung-ho about attacking dug in positions - consider his actions when he reached Vicksburg...
 
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So on the 14th (with fighting beginning around 10AM on that day, as historically) Johnston could have 7,500 in Jackson and be attacked by 24,200 PFD - more than 3:1 odds. If he's able to hold out against that for two days for Ector and McNair to arrive, then 13th Corps alone could hold out against Pemberton for two days even if Pemberton had more than 50,000 troops - and whichever one 2nd Div 15th Corps was in makes things worse.
Not convinced...sorry. But thanks for your detailed reply!
 
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From the top of my head:

1. Jonston not sending Jackson and his command to closely follow the routed Union Army straight into Washington D. C.; reorganize as quickly as possible his army and follow Jackson, ASAP.

2. McClellan not blowing through the thin defenses of Yorktown line with forces at hand.

3. Little Mac not attacking Lee 24 hrs earlier at Antietam.

4. Hooker not remaing at Chancellors vile after his lines had been stabalized after Howards rout. His larger army was still between Lee's forces and those of Jackson's.

5. Braggs turning away from his advantageous position against Buell, and allowing Buell's army to escape. in its retreat from Ky.
 
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1. Jonston not sending Jackson and his command to closely follow the routed Union Army straight into Washington D. C.; reorganize as quickly as possible his army and follow Jackson, ASAP.

Famous as Jackson would become, at Bull Run he was just one of twelve brigade commanders, in his first major action; and his brigade had suffered the heaviest losses, about one quarter of its strength. If the Confederates were going to organize a pursuit, it probably would not have been a matter of following Jackson. Johnston's four brigades suffered most of the Confederate casualties, so a pursuit would probably have been conducted by Beauregard's Army of the Potomac. Perhaps some of our knowledgeable friends can suggest which units were in position and in a state to take the lead.
 
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2. McClellan not blowing through the thin defenses of Yorktown line with forces at hand.
Ooh, another chance for a numbers argument where I know the numbers.

What day in particular are you thinking of that McClellan should have done this?


3. Little Mac not attacking Lee 24 hrs earlier at Antietam.
And a third one!

Since this one has a specific date attached I'll cover it in this post, but I will be interested in the date for Yorktown as well.

So "24 hours earlier" is technically dawn on the 16th, but I'll instead assume midday on the 16th when the fog has burned off.

As of this time, the statuses of the divisions on both sides were as follows:

DH Hill, DR Jones, Hood+Evans - already there on the 15th.
Stuart - already there on the 15th.
This is 14,694 infantry, 4,500 cavalry (and 138 guns including the reserve artillery) in effectives.

Ewell - crossed the Potomac dawn of the 16th after camping south of the river overnight, ca. 4,400 infantry effectives.
Jackson - crossed the Potomac at dawn after having straggled heavily on the march, ~1,600 infantry effectives when they arrived at the field, but more troops straggle in over the course of the day.

Walker - crosses the Potomac at noon at ca. 3750 men after resting at Shepherdstown to bring up stragglers.

Total - about 20,700 inf effectives on the field at noon and perhaps another 4,000 by 1pm (counting 250 stragglers from Jackson as having arrived by noon, which is probably a low bar).


McClellan:

On the field
1st Corps: 8,600 infantry (this is based on Meade's estimate of strength carried into combat) and 46 guns around the Pry House to the Pry (upper) Bridge
Richardson's division and Sykes' division: ca. 6,700 infantry and 30 guns at the Porter (middle) bridge
Artillery Reserve: say 42 guns (42 guns engaged overall, haven't tracked batteries)
Cavalry: ca. 2,500 and 22 guns

At Keedysville etc.
Sedgwick's and French's divisions of 11,117 infantry and 30 guns

At Boonsboro etc.
12th Corps: 7,239 infantry and 22 guns

At Appletown etc.
9th Corps: 11,714 infantry and 32 guns

Hence the decision to send 12th Corps to support 1st makes sense, there was a road to the Pry Bridge.

At noon on the 16th (i.e. after the fog lifted at 1100 hrs), McClellan had around 26,400 infantry, 2,500 cavalry and 170 guns at the area of the Porter Bridge, facing ca. 24,500 infantry, 4,500 cavalry and 186 guns. He has two corps marching to the field (9th and 12th) within range to come into action by nightfall if he goes straight up the middle (that is, attacking down the one road to Sharpsburg) but he doesn't have time to get troops into position for a broad front attack.

So the numbers are actually about equal until 12th and 9th Corps can arrive.
 
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Thoughts?
Five lost opportunities? Neat question. I'll probably forget something really important, but here is a quick list:

1. First Bull Run. The US Army was a mass of confusion due to the loss of many officers who defected to the Confederacy, but the Confederate Army was still in its formative stage. The Army that pre-existed the war really should have won the fight. A convincing victory for the Union might have dashed the hopes of the rebelling states. This was a missed chance to crush the rebellion.

2. Gettysburg. Lee's failures here are well-known, but the original idea about trying to force a political decision to end the war through putting a scare into the northern populace was a gamble worth taking at that stage. It didn't work, but it was a missed chance for the Confeds.

3. The weeks prior to Chickamauga. The federals had Bragg's Confeds on the run but Rosecrans allowed his army to extend itself too far while giving chase and he got caught. A better job of chasing the Confederates without over-extending his own forces might have allowed Rosecrans to drive Bragg deep into Georgia months earlier than Sherman eventually did. This could have shortened the war.

4. Ford's Theater. Had someone been around to give an effective defense of the President, Lincoln might not have been killed. A full second term for Lincoln would not have shortened the war but it might have made for a more effective Reconstruction. The mis-management of the effort by presidents Johnson and Grant did as much damage to the nation at large as did the war itself.

Best I could do!
 
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2. McClellan not blowing through the thin defenses of Yorktown line with forces at hand.
Since no date has been forthcoming, I'll just have a look at the issue of the "thin defences".

The first thing we need to realize is that Magruder's comments about his weakness are in many cases either mistaken or lying. He claims to have to defend a line over ten miles wide, but the Yorktown line is simply not that wide:

Yorktown1862.png



The scale in the bottom left shows that the actual line is only a few miles long, and even that sort of overstates things because there are only a few crossing points of the Warwick. (The rest of it is deep enough that it cannot be forded.)

The crossing points, and the routes by which McClellan's force approached the Warwick line on the 5th, are shown below.

Warwick_approach.jpg

(note that the crossing point around Garrow has no road leading to it, and the same is true of Wynns Mill - neither of these is a road way to cross the Warwick and it requires recon to find them, which leads to a delay.)

On the 5th, McClellan ordered both his approaching columns to attack by bayonet charges if necessary - the left at Lees Mill and the right at the gap between Yorktown and the Warwick (the Red and White redoubts). However, neither column was able to successfully attack because of the volume of enemy firepower.

On the 6th, McClellan did not re-order an attack. On the 7th it began raining hard enough to shut down all movement for a few days.
So how many troops were there in the Warwick line on the 5th and the 6th?

The best estimate we can obtain is by looking at the actual per-regiment reported strengths from late April and cross-referencing this with regimental arrival dates.

The troops who were at Yorktown on or before the 5th of April were:

Brigade Regiment Strength Type
1: McLaws 5th LA 744 Inf
2: McLaws 10th LA 595 Inf
3: McLaws 15th VA 476 Inf
4: McLaws Noland Battalion 162 Inf
5: McLaws Garrett 50 Art
6: McLaws Young 57 Art
7: Cobb 16th GA 488 Inf
8: Cobb 24th GA 660 Inf
9: Cobb 2nd LA 782 Inf
10: Reserve 10th GA 582 Inf
11: Ewell 32nd VA (1 coy) 29 Inf
12: Ewell 52nd Va Mil 30 Inf
13: Ewell 68th Va Mil 20 Inf
14: Ewell 115th Va Mil 40 Inf
15: Ewell Old Dom Rifles 60 Inf
16: Ewell Allen's battalion 500 Art
17: Ewell Companies Art 121 Art
18: Colston 3rd VA 550 Inf
19: Colston 13th NC 575 Inf
20: Colston 14th NC 625 Inf
21: Wilcox 9th AL 550 Inf
22: Wilcox 10th AL 550 Inf
23: Wilcox 11th AL 656 Inf
24: Wilcox 19th MS 800 Inf
25: Wilcox Stanard 60 Art
26: Winston 8th AL 800 Inf
27: Winston 14th AL 700 Inf
28: Winston 14th LA 750 Inf
29: Winston Macon 60 Art
30: Ward 2nd FL 530 Inf
31: Ward 2nd MS Battalion 360 Inf
32: Rains 13th AL 474 Inf
33: Rains 26th AL 283 Inf
34: Rains 6th GA 703 Inf
35: Rains 23rd GA 370 Inf
36: Rains 19 batteries, Yorktown 1151 Art
37: Crump 46th VA 356 Inf
38: Crump 9th VA Mill 29 Inf
39: Crump 21st VA Mill 39 Inf
40: Crump 61st Va Mill 201 Inf
41: Crump Det Cav 18 Cav
42: Crump Det East Shore 58 Inf
43: Crump Matthews Lt Dr 40 Cav
44: Crump Armistead 46 Art
45: Crump Heavy Art 332 Art
46: Reserve Arty Pendleton 720 Art
47: Magruder Magruder's cav 990 Cav
48: Wise Wise and Hampton cavalry 700 Cav


Which totals

Type Strength
1: Inf 14627
2: Art 3097
3: Cav 1748


That's what's there the day McClellan reaches Yorktown.

As for arrivals on the 6th:

Brigade Regiment Strength Type Arrival
1: Cobb Cobb's 594 Legion April 6
2: Early 20th GA 560 Inf April 6
3: Early 23rd NC 540 Inf April 6
4: Early 24th VA 740 Inf April 6
5: Early Jeff Davis 80 Art April 6
6: Rodes 5th AL 660 Inf April 6
7: Rodes 6th AL 1100 Inf April 6
8: Rodes 12th AL 550 Inf April 6
9: Rodes 12th MS 650 Inf April 6
10: Rodes King William 80 Art April 6

Type Strength
1: Legion 594
2: Inf 4800
3: Art 160


Their dispositions on the 6th are:

Warwick Line_6th.jpg



I do not see a way to simply roll over Magruder's force. He has ~2,000 infantry to oppose each of the crossing points (with 5,000 in the rear as reserves if need be) and another 6,500 covering the mile or so from the head of the Warwick flooded region to the York river, plus over 3,200 gunners (which is to say, on the order of 160 guns). As a point of trivia interest it is almost as strongly defended as Vicksburg in terms of total men*, and notably more concentrated per mile.**

*After the casualties in the field battles Vicksburg's defenders were not more than 25,000 men all told, and counting troops that arrived on the 6th the defenders of the Warwick line were also 25,000 men all told. It is unclear if the categories were the same, but if they differed it is in favour of the Warwick forces being larger.
** The Vicksburg defences are about 6.5 to 8 miles of perimeter that all needs to be defended, while the Warwick line can be concentrated on a few points of attack and is only about five miles long counting the whole length.

There were missed opportunities at the Warwick line, but "just roll straight over them" is not one of them.
 
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If anyone's interested, I can do a quick precis of the alternate possibilities at the Warwick line which can be considered missed opportunities. It's worth considering though that in no case would this gain more than about a month, so it's not necessarily a "top five" missed opportunity.
 
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Five lost opportunities? Neat question. I'll probably forget something really important, but here is a quick list:

1. First Bull Run. The US Army was a mass of confusion due to the loss of many officers who defected to the Confederacy, but the Confederate Army was still in its formative stage. The Army that pre-existed the war really should have won the fight. A convincing victory for the Union might have dashed the hopes of the rebelling states. This was a missed chance to crush the rebellion.

2. Gettysburg. Lee's failures here are well-known, but the original idea about trying to force a political decision to end the war through putting a scare into the northern populace was a gamble worth taking at that stage. It didn't work, but it was a missed chance for the Confeds.

3. The weeks prior to Chickamauga. The federals had Bragg's Confeds on the run but Rosecrans allowed his army to extend itself too far while giving chase and he got caught. A better job of chasing the Confederates without over-extending his own forces might have allowed Rosecrans to drive Bragg deep into Georgia months earlier than Sherman eventually did. This could have shortened the war.

4. Ford's Theater. Had someone been around to give an effective defense of the President, Lincoln might not have been killed. A full second term for Lincoln would not have shortened the war but it might have made for a more effective Reconstruction. The mis-management of the effort by presidents Johnson and Grant did as much damage to the nation at large as did the war itself.

Best I could do!

Interesting! I never thought about the Ford's Theatre angle. Most folks look at either ways to win the war, or ways to avoid it. Very few look at post-war reconstruction opportunities. Well done!
 
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Too easy. There were a great many missed oppotunities but only two that might have ended the war.

1) First day at Gettysburg. Jackson on the left would not have hesitated a second, the Union forces would gave been swept off of Cenerary Ridge and the whole affair could have forced Washington to sue for peace.

2) Gordon being prevented from attacking the naked Federal right at the Wilderness until it was too late in the day. Might have sent the entire army running
.
 
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1) First day at Gettysburg. Jackson on the left would not have hesitated a second, the Union forces would gave been swept off of Cenerary Ridge and the whole affair could have forced Washington to sue for peace.
How's the force balance? Remember that the fewer Union troops on the field the less catastrophic a defeat is.

There are definitely opportunities for a decisive victory at Gettysburg, or a victory followed by a shattering of the Army of the Potomac, but I've generally felt they refer either to better march order in the week or so leading up to the battle (so Lee's forces can arrive on the field earlier) or things going as planned for Lee's day two attack, or the like.
 
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Too easy. There were a great many missed oppotunities but only two that might have ended the war.

1) First day at Gettysburg. Jackson on the left would not have hesitated a second, the Union forces would gave been swept off of Cenerary Ridge and the whole affair could have forced Washington to sue for peace.

2) Gordon being prevented from attacking the naked Federal right at the Wilderness until it was too late in the day. Might have sent the entire army running
.
1- Jackson was not there, so no missed opportunity. Had Jackson been there, he would have had no better guidance from army HQ than Ewell.
Understand Lee was asking 2 divisions to push 2 Federal Corps off ridges that had required 4 CSA divisions to run up on the ridges.
 
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1- Jackson was not there, so no missed opportunity. Had Jackson been there, he would have had no better guidance from army HQ than Ewell.
Understand Lee was asking 2 divisions to push 2 Federal Corps off ridges that had required 4 CSA divisions to run up on the ridges.
It is worth considering whether the Federal corps in question were able to fight their full potential - a lot of 11th Corps for example was probably not up to much further fighting on Day One, in particular, because those men had been in two engagements so far and broken in a rout at both of them.
Counting by brigade to see how many brigades had merely withdrawn rather than broken would be an interesting project.
 
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As for the missed opportunities during the Warwick Line operations. They are, roughly in temporal order:


Not alerting the CSA for another few days. Heintzelmann's operation was what alerted the Confederates to the movement onto the Peninsula, and if that hadn't happened (and thus the CS reinforcement and movement had been delayed a few days) you could have either got the capture of Magruder's (small) force in the Big Bethel area (with a landing by 1st Corps south of Yorktown but north of the Big Bethel area) or simply no time to rush reinforcements to Magruder; you do still need to overcome the garrison of Yorktown itself, though, as it's a bastion fort.

1st Corps available to promptly move on Gloucester Point. 1st Corps was the formation with the amphibious landing capability. In this case taking Gloucester Point offers the possibility of allowing ships up the York straight off and rendering Confederate supply at Warwick untenable.

Bombardment of Yorktown with ships. Simple enough; using heavy weapons to attack Yorktown by sea offers the prospect of reducing it earlier than the siege guns offered that prospect by land. The fort was not well defended against attacks from ships running past overnight (which was a common tactic in the West) while it only had one gun able to range out as far as rifles, so some shipboard rifles would have also been able to make good practice.

The attack on the 16th at Garrow Ridge goes off. This was intended to be a five-division assault with operational surprise against the weakest part of the line - a "deliberate attack" with engineering support to identify the crossing point - but a misguided probing attack both ruined the surprise (alerting the Confederates) and collapsed the dam they were going to use.

None of these really gain you a huge amount of time. The best combination of them is probably the CSA not being alerted, 1st Corps being landed behind Magruder's forces (to trap them) and then the naval reduction of Yorktown because that opens up the York within a few days of the alarm being given, but even then you only get about a month.

A full corps' worth of sealift is available at the end of the operations, and troops are on ship.
This on the other hand is the big one - the ability to land a full corps at Eltham's Landing the day after Yorktown is abandoned offers the prospect of putting a "cork" across the Peninsula strong enough to stop Johnston from getting out and early enough to dig in. (As it was there was only enough transport for one division at a time, and since Franklin's division had disembarked to add to McClellan's planned assault against the line once the guns had done their work it took them a while to re-embark - so transporting enough troops to block about 60,000 Confederates would take too long.)
 
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It is worth considering whether the Federal corps in question were able to fight their full potential - a lot of 11th Corps for example was probably not up to much further fighting on Day One, in particular, because those men had been in two engagements so far and broken in a rout at both of them.
Counting by brigade to see how many brigades had merely withdrawn rather than broken would be an interesting project.
i doubt there were 10,000 Federal infantry formed on the ridges. My concern was the artillery that the Confederates could not answer.
Assuming the CSA troops pushed the infantry, and the guns limbered up, Lee would have lost at least 20% of his army gaining a town with little value
 
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