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Originally Posted by Mason Malmuth
1. If Jackson lives, the Southern victory at Chancellorsville might have been even more over whelming which could have allowed Lee to threaten Washington.
And if Lee threatens Washington, what does this get him? Washington was heavily fortified and it would have been easy for the government to uproot and move further North. If anything, this might have made things easier on Lincoln if a few Copperheads could have found their way into Confederate hands during the evacuation. The Union doesn't surrender even if Lee takes Washington. There are cases to be made for Lincoln's prospects getting weaker, but also cases to be made for Northern resolve increasing if the press (which was quite active) played up Southern perfidy sufficiently.
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2. If Jackson goes north with Lee to Gettysburg, the Confederate army probably would have preformed much better.
The question is "to what extent?" If Jackson is there, do the Confederates seize the high ground on the first day? If the Confederates seize the high ground, does the Union army engage at all, or do they simply move around and look for a new spot? If everything else remains the same, but Jackson has command of Longstreet's units, do the Confederates magically do better at Devil's Den or on Little Round Top? It's hard to see how. Once Lee makes the disastrously bad decision to fight at Gettysburg, the Union victory isn't entirely a foregone conclusion, but they're heavy favorites. And if we're playing the "what if" game, if Grant had been in command instead of Meade, it's entirely likely that Lee's whole army is destroyed or captured trying to cross back over the Potomac. Lee had enormously good fortune to go up against commanders as passive as McClellan and Meade when he made his biggest strategic blunders.
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3. Jackson possibly could have been sent to the West to command The Army of Tennessee and he definitely would have been a much better commander than Braxton Bragg.
This is a more interesting case to be made, as the western theater was arguably more important to the overall war effort than the scrum on the Virginia-Maryland border.