“Civil War” is a contradiction in terms, and the war itself was a series of strange turns and ironic events. The two most important Union generals couldn’t be more different. George McClellan was destined for greatness. He was admitted two years early to West Point, graduated second in his class, and went on at the age of 34 to be second in command for the Union in May 1961 under Winfield Scott, taking full command in July.

Scott was more than twice McClellan’s age and one of the young nation’s most admired military heros. But Scott was old. McClellan poured his energy into doing all those things you do when you’re undermining an opponent – badmouthing through the whisper network, cutting people out of meetings, and assuring the boss that he can do it all. McClellan succeeded in his goals, and he replaced Scott.

McClellan was perhaps too successful. Unlike Ulysses Grant, he had never known low rank or defeat. And when he became the leader of the Union military, he froze. He overestimated his enemy’s strength, which resulted in the humiliating defeat in the first major battle of the Civil War at Bull Run.

You have to take risks to win a battle, and McClellan just couldn’t bring himself to take any risks. He was always on the cusp of action, but thwarted by the imagined machinations of the Confederate machine. He blamed others: he wrote to his wife that the cabinet members were “a most despicable set of men” and Lincoln himself “a well-meaning baboon.”

Grant ranked 21st out of 39 at West Point. He was forced to leave the army in 1854 because of his drinking problem. He rejoined in June 1961, right before McClellan took over as general. Grant was ordered to begin a river campaign to move south and take Fort Henry in Tennessee. Grant was afraid as he set out for the enemy: “my heart kept getting higher and higher until it felt to me as though it were in my throat. I would have given anything then to have been back in Illinois, but… I kept right on.” The Confederates fled as he approached, and Grant realized that the enemy colonel “had been as much afraid of me as I had been of him. This was a view of the question I had never taken before; but it was one I never forgot.”

Grant’s campaign waged successful skirmish after successful skirmish, and ultimately gave the Union much-needed momentum. Grant was known for making do with the resources on hand, never asking for reinforcements and never complaining. He was not a perfect leader, but he was good. As Lincoln observed, he did the work.