In retrospect he was always victorious. That winter spent losing toes to frostbite was a glorious success; it cemented his legend. His series of defeats, routs and retreats swelled to a fine triumph, since he lost less (much less!) when forced to withdrawal than anyone could have expected.
Well, what did you think? Classic war of asymmetry. Wear them down, minimize your own losses, maximize your advantages. Facing a better-trained, better-equipped, better-supplied force, accept that you’re going to lose more often than you win. But entrench yourself: make losing cost them more than it does you. You have to want it more.
And later, after the confederation he’d fought for and declined to lead had collapsed in on itself (unwieldy), he deigned ascend what was less than a throne. And his first act, his first major act, was to put down a new rebellion. Our grain, our whiskey, our money, they cried. Free travel on the Mississippi! He sets out with his army of dervishes behind him and crushes them. Absolutely destroys them.
In retrospect, like all his other decisions, it turns out to have been the right move.