Question

What quality of General McClellan may have hurt the Union and helped the South?

Answer 1

He was too cautious

Explanation:

General McClellan was a rather great tactician, in actuality, he had quite a few stratagems for defeating the South (he also graduated from West Point). Matter of fact, he was called "The Young Napoleon". He was also known for being too caring for his soldiers, and not wanting to spare them at any risks. This allowed for the South to get away at a moments were McClellan could've pounced and obliterated the South, but decided not to due to loss of life. This did earn him the affection of his soldiers, but not of his supervisors. This is why he was discharged after failing to pursue Lee after the Unionist victory at the Battle of Antietam (https://en.wikipedia.org/wiki/Battle_of_Antietam), because of his circumspection.