“Lee wins and then what?”...head straight down rt.97 into D.C....that was the whole point of Pickett’s charge...break on thru to the other side.
“He’s hundreds of miles behind Union lines”
...not as bad off as you would think....it’s only about 55 miles over to Harper’s Ferry....less to Point-of-Rocks....besides, across the Mason-Dixon line in Maryland there were many families whose sons were in his army...and many more who were Southern sympathizers....Lee’s problem would have been the longer he was outside of VA the greater the chance he would be trapped....he went North in 1862 and 1863 and was lucky to get out both times.
Lee could have invested DC on many occasions. He never did because he knew that his army was too small and too poorly equipped to take Washington under siege conditions - his army's forte was attacking infantry on the march, something they did supremely well.
Lee also knew that you cannot besiege a city with access to the sea effectively if you do not possess the ability to blockade it - without a blockade the attackers automatically double or triple the cost in men and materiel.
Lee also realized that even if he managed to take Washington, by the time he reached the city proper the US government would already be gone and administering the nation from New York or Boston.
Lee knew that the cost/benefit of taking Washington was a huge losing proposition for the Confederacy. His goal was to defeat the Army Of The Potomac in detail and remove it from the chessboard.
besides, across the Mason-Dixon line in Maryland there were many families whose sons were in his army...and many more who were Southern sympathizers....
Lee's Army had already been through Maryland in the Sharpsburg campaign six months before. He gained well less than a thousand new recruits and got a polite but not very passionate welcome.
Maryland only had a grand total of eight or nine regiments plus four or five random companies in the Confederate forces. In contrast, Maryland had more than 35 regiments in the US Army.
To provide some comparison, Texas had an 1860 population of 600,000 and fielded more than 100 regiments in the Confederate forces. Maryland had an 1860 population of 700,000 yet fielded less than 10% of the strength for the Confederacy that Texas did.
Lee’s problem would have been the longer he was outside of VA the greater the chance he would be trapped....he went North in 1862 and 1863 and was lucky to get out both times.
People have pointed out some aspects of Lee's Northern strategy on this thread. My opinion is that his strategy contained all of the following:
(1) Resupplying his forces from the well-stocked Federal larder.
(2) Keeping his troops far away from Richmond to prevent them from being redeployed to other theatres.
(3) Humiliating the US Army by forcing it as far back into its own territory as possible with an eye to (A) boosting anti-war sentiment among Democrat traitors, (B) sending a message to foreign powers that might spur intervention on the Confederacy's behalf, (C) keeping the US Army from foraging in VA.
(4) Destroying the rail and telegraph links between the East and the Midwest. During the Sharpsburg campaign this was paramount - if Bragg had made it to Cincinnati and Lee had decisively controlled Harper's Ferry, they would have effectively as good as split the Union in two again.
(5) Most important: destroy the Army of the Potomac.