Most interesting discussion. A couple of examples of military brilliance and never losing a battle despite commanding smaller armies comes to mind: Alexander the Great and "Stonewall" Jackson. I am a humble truck driver, not a military historian so I may be way off but if memory serves Alexander is considered the greatest military genius of all time. Generally, his armies(at least at the beginning of his career) were far smaller than the "superpowers" of the day. Specifically, Alexander faced an army six times larger than his own. I believe the opposing commanders' name was Darius. I don't recall the battles' name but certainly Alexander crushed an army outrageously larger than his own though manuever and his own personal genius. No possibility of attrition here. Of course, the stomping of Darius' army was only a warmup and Alexander went on to conquer everything he set his sights on.
Briefly, about General Jackson. Jackson was a humble, strictly religious man whose military genius was unquestioned even in his brief lifetime. After his famous victories, he became well known throughout the world. As I recall, Jackson never lost a battle and was constantly badly outnumbered by Union armies. He was a master of manuever and surprise, always appearing where the enemy least expected him and in greater numbers than they. The following is pure speculation but if Jackson had not been killed by friendly fire, he and Lee might very well have been able to reinvade the North with unknown consequences to the outcome of the war. I think Jackson is the only military genius who did not publicly display cockiness or smugness with his own ability. Indeed, he humbly thanked his Creator for his victories and, I think, refused to take credit. Perhaps this is one brilliant maneuverist(who never lost a battle) that Jason could like. My two cents.