This still puzzles me. With only one third of his army General Lee held back the entire Union army for two days and left Maryland unmolested but he is the loser?

I went back and re-read General Lees original goals.

1. To occupy the Northern part of Virginia vacated by the Union army in time to take advantage of the fall harvest.

This he did.

2. To cross the Potomac to...

To prolong a state of affairs in every way desirable, and not to permit the season for active operations to pass without endeavoring to inflict further injury upon the enemy, the best course appeared to be the transfer of the army into Maryland. Although not properly equipped for invasion, lacking much of the material of war, and feeble in transportation, the troops poorly provided with clothing, and thousands of them destitute of shoes, it was yet believed to be strong enough to detain the enemy upon the northern frontier until the approach of winter should render his advance into Virginia difficult, if not impracticable. The condition of Maryland encouraged the belief that the presence of our army, however inferior to that of the enemy, would induce the Washington Government to retain all its available force to provide against contingencies, which its course toward the people of that State gave it reason to apprehend. At the same time it was hoped that military success might afford us an opportunity to aid the citizens of Maryland in any efforts they might be disposed to make to recover their liberties. The difficulties that surrounded them were fully appreciated, and we expected to derive more assistance in the attainment of our object from the just fears of the Washington Government than from any active demonstration on the part of the people, unless success should enable ns to give them assurance of continued protection.

This he did as well. He engaged the Union army and hurt it at every point capturing key places and supplies. Lees actions stunned the Union command into what Lee called a "quiescent" state for over two months not moving again towards Richmond until November 17, 1862.

As for getting aid to the people of Maryland he hoped he could but he thought the odds were against him. He movement was to mess with the minds of Washington more than to actually cause a rebellion in Maryland.

"we expected to derive more assistance in the attainment of our object from the just fears of the Washington Government than from any active demonstration on the part of the people"

So why did he lose?

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David Upton