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So in 1862, Lee crossed over into Maryland east of South mountain, and criss-crossed this way and that through the mountains and over the Potomac to capture the garrison of Harpers Ferry, culminating in the crisis of September 14 when McLaws's command was bottled up in Pleasant Valley. His initial goal had been to force a battle with the main Union field army by threatening Washington, Baltimore, or Harrisburg from Frederick Maryland, but he probably overreached for the opportunity to bag Harpers Ferry, and lost thousands of men to straggling as he scrambled to defend against McClellan's thrust through South Mountain.

So what if instead, he crossed the Potomac west of South Mountain and marched up the Cumberland Valley with his army of 69,000 veterans, with the goal of fighting a battle somewhere in southern Pennsylvania or northern Maryland east of South Mountain? Longstreet with Jones, Hood, and Walker could cross South Mountain through Monterey Pass, while Jackson could use Cashtown gap, with McLaws and Anderson marching on Harrisburg? He could bag the garrison at Martinsburg, which would probably dissuade the garrison at Harpers Ferry from any threatening action, and without major rivers or mountain ranges dividing his army, he could face McClellan's army without needing to desperately scramble his men into position, and thus deploy more men. At the time, about 18,000 men in the Army of the Potomac were brand new; they'd just completed their organization and equipment, and had conducted no training. Most of the rest of the army was still smarting from defeat at Bull Run, which was partially alleviated by the victories at South Mountain.
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